How did I get here? Not here in the world, but here in this point in my life. This wasn't what I had imagined. This isn't the way it was supposed to go, is it?
Here I stand, a man dressed as a woman, quite convincingly I may add, as another man passionately plants a deep kiss on my lips. My wife stands off to the side in utter shock, eyebrows raised and jaw agape. What decisions led me to this point? Could this have been avoided, or was this always the road I was meant to travel? Do I give into my impulses and allow this to continue, or do I put a stop to everything right now, blowing my cover as a crossdresser and facing the consequences?
To get these answers, I guess we'll have to go back a few weeks to when this all started; back to when my wife Victoria caught me dressed in women's lingerie. In all truthfulness, I guess this all started when I was a young boy and decided that I wanted to see what it felt like to wear a pair of women's stockings. Over the years, that developed into full on crossdressing, including lingerie, outfits, wigs, makeup, and a collection of heels that rivals that of my wife.
Normally, I was very safe about my crossdressing. I had been closeted about it for at least 15 years, and I always made sure that I have several hours of free time with my wife out of the house before venturing down that path. That gave me the time to grab all of my things out of storage and enjoy a little time dressed in the chosen outfit. It usually wasn't sexual, I just enjoyed the feeling of the transformation from man to woman, although sometimes I would get myself all turned on at the sight of the woman looking back at me in the mirror.
I am six foot and about 170 pounds; a little large for a woman, but average sized for a man. I have a trim athletic build, nice legs, and a bit of a booty. So with a little bit of shapewear, I'm able to pull off a convincing woman, albeit a tall one, especially in heels.
On this particular day, my wife had run out to get lunch and do some shopping with a girlfriend. She told me that she expected to be gone for about 3 to 4 hours. It was tight, but it would be plenty of time to get an hour dressed as my female persona, who I called Ashley, and still have time to clean up all the evidence before Victoria returned. I had put on my 38DD breast forms and gotten my wig and makeup all to my liking. Just as I pulled on a pair of tan stockings to go with the green bra, panty, and garter set that I was wearing, my wife burst through the bedroom door.
I don't know which of us was more shocked, but I froze like a deer in headlights, unsure of what to say or do. Victoria, in her initial shock, thought that I had another woman in the bedroom.
"Who the fuck are you?" she started to say. "Wait...Aaron? Is that you?"
I was frozen stiff. Unable to respond, yet too afraid to run away. I was busted.
"Oh my God," she laughed. "What the fuck are you doing?"
"Um, what are you doing home?" I finally uttered out, sheepishly.
"Well, I had almost gotten to the restaurant when Holly called and said she had something come up and wouldn't be able to make it, so I came home to see if you wanted to join me for lunch." She laughed again. "But it looks like you already have plans."
"Victoria, I'm so sorry. It's not what it...well it is, but...I don't really know what to say." I stumbled about my words, unsure of how to explain this shocking sight to my wife.
I took off the wig and began pulling off the stockings and lingerie, uncomfortably aware that my wife was watching me like a hawk.
She cocked her head, intrigued, but clearly confused by the situation. "I didn't know you had this side of you Aaron. I mean, I have several questions, but I can't help but notice how nice your legs look. You honestly had me thinking you were a woman until I saw your garish makeup."
I frowned. "Yeah, I'm not so good with the makeup. Lack of experience I guess."
I paused, unsure of how she was taking this. "I'm confused, are you pissed?"
Victoria still stood there, eyeballing me as I removed my breast forms.
"I'm not exactly sure," she said. "First off, is this just something you do, or were you about to meet with someone? Are you gay, or trans? Are you looking to transition to female permanently? And how long has this been going on? Looking at your suitcase full of clothes and shoes, I'm guessing it's been happening for quite some time."
I did my best to explain and answer all of her questions, and to her credit, she remained quiet and listened. I'd told her that it started when I was young, well before we had even met, let alone got married. I had always figured it was a phase I'd eventually grow out of, but instead I only traveled deeper and deeper into the rabbit hole.
We discussed my affinity for women's fashion and shoes. She admitted that she did find it weird that I always knew the perfect shoe for her outfits whenever she was getting ready. I showed her my entire collection of clothing, shoes, lingerie, stockings, and of course makeup and accessories. Finally I showed her my several pairs of breast forms, hip pads, cinchers, and other shapewear. It was actually quite a relief to finally get all of this off my conscience.
She finally breached the subject of my sexuality again. "So, what does all this mean? Are you gay, bisexual, trans?"
I just shrugged. "I...I don't really know. I can tell you that I'm not gay. I mean, I don't have any desire to be with a man, as myself or my female personality. And I love women, maybe too much. Perhaps that's why I enjoy being one."
She smirked, "Have you ever played with a dildo?"
"No!" I blurted out, maybe a little too aggressively. "No, but I guess I have thought about it."
Victoria just pondered my answer in silence.
"I...I have put a finger inside though. I didn't not like it."
Perhaps I said too much. Victoria continued to stare at me in silence, but at this point I couldn't stop myself from talking.
"I've also talked with other crossdressers and trans women on social media, like Reddit and Kik. I guess I find them attractive. But I've never looked for a hook-up, I promise." I continued to ramble on nervously. "It's always just been to share and get tips from others like me. Again, I'm so sorry."
Victoria finally broke her silence. "No need to be sorry for being who you are. I mean, I wish you would have been honest with me from the beginning. I'm hurt that you felt you couldn't trust me with this."
It just occurred to me that she now had dirt on me. Dirt that I did not want getting out to my family, friends, and coworkers.
"Victoria, please...you can't tell anyone about this." I stammered.
She just shook her head. "Why would I tell anyone? It obviously took a lot of effort for you to confess all this to me, even though you only did it because you were caught red handed. I'm still your wife and I will keep all of this in confidence."
"Thank you," I pleaded.
"But," she said defiantly. "I don't want you sneaking around and lying to me anymore. I can deal with your alter persona, but I won't tolerate lying. I have always been honest and up front with you, especially when it comes to extramarital sex."
I just nodded in shame. She was right. She had always been honest with me. It was me who drove us to an open marriage. More accurately, it was me who practically begged my wife to have sex with other men. It was always my fantasy to watch her fuck another man. It took a lot of reasoning and pleading, and it almost destroyed our marriage, but she finally graced me with the experiences I craved.
Victoria had always been up front about what she expected from me and what she planned with other men. She would always tell me when she'd receive a proposition from another man, and it would always be a unanimous decision on whether or not she would accept. Sometimes I got to watch, and sometimes I would just hear about it the next day, but if one of us said no, then that was it...no questions asked.
I felt even more shame for keeping my true self from my wife.
"You're absolutely right," I admitted. "I've been selfish. I won't keep anything else from you."
Victoria smiled. "Great! I've got just one last question for you. Have you ever gone out as...um"
"Ashley," I informed her. "Ashley Ryann, actually."
"Ashley, huh? I like that. Have you ever gone out as Ashley, or do you just hang around the house?"
I slunk back into the bed. "No, never. I've always been terrified that someone I know might recognize me. I considered staying at a hotel out of town and going to the bar as Ashley, but I could never bring myself to do it. Besides, like you said, my makeup is garish."
Victoria grinned, "I could easily help you with that."
"Really?" I beamed. "I would love that."
I couldn't believe how this was turning out and I couldn't believe how accepting my wife was being. I would have told her years ago if I had thought this reaction was even possible.
"Of course," Victoria continued. "Actually, that really may help me out with something I've been meaning to ask you about."
She had my full attention now. "Really? What is it?"
She sat by me on the bed. "Well, you know Mike from my office right?"
I knew Mike alright. He didn't know about our open relationship, but he knew that Victoria was married. That didn't stop him from coming on to my wife every chance he got. It actually bordered on sexual harassment.
In fact, Victoria had often told me about his advances on her. She always loved the attention, but she was usually put off by how forward he was. She described him as a frat boy, only after as much pussy as he could get his hands on. Every woman was just a conquest to him, whether or not she was spoken for.
"Yes, I'm aware of Mike," I responded. "What did he do now?"
"Well, you know my feelings about him, but he keeps pestering about going to this new bar in the city with him. He wants to take me and wants me to bring a girlfriend for his buddy."
Taken aback, I spit out, "And what did you tell him?"
Victoria shrugged, "I told him no, of course. But if you were to go as my girlfriend, I think that might be fun."
I couldn't believe what I was hearing. Just an hour prior I was afraid that my marriage was over, and now my wife was suggesting taking me out on a date as my female persona. On top of that, she'd be on a date with a guy she had always claimed to hate.
"I'd love to go out with you," I said eagerly. "But I'm not interested in dating a guy. Besides, I thought you couldn't stand Mike."
"To be completely honest, you're right. I can't stand Mike," Victoria admitted. "But a little birdie told me that he's hung, and I figured if it's just sex, then what's the harm? As long as you approved, of course."
I just sat there stunned. I wanted to go out as Ashley, but I wasn't too keen on the idea of being on a double date. Also, I never really cared who Victoria fucked, but I never thought she'd want Mike. I was completely caught off guard.
"If we did this, I wouldn't fuck him on the first date. I'd be right by your side all night to make sure you were comfortable. If at any point you wanted to stop, we'll leave and call it quits." Victoria did her best to calm my fears and reassure me.
"I don't know. I just don't think I can do it," I admitted. "I'm sorry."
Victoria didn't let up. She just changed her tactic.
"How about this? How about you get dressed back up as Ashley and I'll help you with your makeup. Then we'll go shopping...you can take Holly's place. We'll buy you an outfit or two. Just to get you comfortable as Ashley in public. If you still don't want to do the double date afterwards, I'll drop it."
"Right now?" I asked, incredulously.
"Yeah, right now." She was practically begging me to join her as Ashley.
How could I turn that down. A chance to finally present myself as Ashley to the world, and a shopping trip with my wife to buy clothes for me. I was practically floating at the prospect.
"Okay," I said eagerly. "Where do we start?"
Victoria eased me into it gently. "Why don't you pick out an outfit to head to the mall, and once you're dressed, I'll do your makeup and give you some pointers."
I sprung into action. So many options. I had never actually picked an outfit for me to venture out as Ashley. Most of my clothes were sexy and a tad slutty. What would I wear to the mall?
I put the lingerie set away and grabbed more modest undergarments; a black mesh bra and matching thong. I also grabbed a pair of black sheer-to-waist tights. I worked my way back into the breast forms. It was a full vest version that I had to pull over my head. It went from mid-neck down to a few inches below the breasts and covered my shoulders as well.
I threw a small pair of hip pads in the tights to help with my figure. I had several pairs, but opted with a more realistic version, rather than some plastic fantasy. Finally, I put on a modest maroon colored dress. It was a U cut neck, but it was high enough that it didn't show any cleavage. The hem was knee length ansent, had a panel of lace and a tie up the left leg. I topped it off with a black choker to hide the transition from breast plate to skin, and then threw on a pair of black ankle boots with a 4 inch heel.
I normally wore a long, bright red wig. It was my fantasy look and I loved how it highlighted my face. I resigned myself to a wavy shoulder length dirty blonde wig, however, as I was too afraid to draw attention to myself at the mall.
Once I had my outfit in place, I turned to my wife. "How do I look?"
"I love it!" She beamed. "Now let's work on that makeup."
She took my hand and walked me to the bathroom. Victoria said that I had actually done a really good job on the foundation and the contouring, but I really messed up the eyeliner and eyeshadow. She also said that the bright red lipstick was a little too aggressive for going to the mall. She fixed me up with false lashes, a smoky eyeshadow, and a flawless liner with a wing. Victoria topped off the look with a soft pink lip gloss.
"There," she said. "I wouldn't know you from Adam. You look amazing. Have a look," she said as she motioned to our full length mirror.
I just gawked at the woman that stared back at me. I always thought that I had done a pretty good job in my transformation, but with my wife's help, I finally felt like a complete woman. Of course I still sounded like a man.
"I'm in love," I admitted. "But you'll need to help me with my voice."
"We can work on that a bit in the car, but I wouldn't stress it too much just yet. We live in a trans friendly town, but you'll definitely need to soften your tone. I can help."
I couldn't believe I was about to head out of the house. The butterflies in my stomach were relentless. Normally I could work a six inch platform heel like a professional dancer, but I felt wobbly in my chunky four inch boots.
Victoria smiled at me and took my hand. "Are you ready to introduce Ashley to the world?"
"I guess no better time than the present," I answered.
She led me to the car. I got in on the passenger side and she drove us to the mall. It was probably for the best. While I was comfortable walking in heels, I had never driven. On top of that, I needed to focus on my voice.
It was a short drive, but we made good progress. She helped me to raise my pitch without sounding too fake or breathy. It still sounded weird to me, and I had to focus really hard to not lose character, but it was better. We sat in the parking lot a few extra minutes to work on it before I finally built up enough courage to finally step out of the car.
"Are you ready?" Victoria asked.
I gave her a quick kiss on the lips. "Let's do it. Thank you for this. I really appreciate your understanding."
My wife just smiled back and watched as I stepped into the world for the first time, born anew. I waited, and she eventually joined me at my side and walked with me into the mall. At only 5'5", I towered over Victoria, especially in my 4-inch heels. I felt like every single person that we passed was staring at me and could see right through my charade. Victoria sensed my apprehension and reached out to grab my hand.
"You're doing great," she whispered.
"I feel like every person here is pointing and laughing at me," I said shakily.
Victoria reassured me. "Of course you do. You are way out of your comfort zone, but I promise, hardly any one is looking at you, and those that do only see an attractive woman."
"A gargantuan woman," I corrected.
She sighed, "There are plenty of women that are taller than you babe. Just relax. Let's head into Akira and find you something cute."
Victoria knew exactly how to calm my nerves. She had never spent any time with Ashley, but it was like she had known her her entire life. Focusing on the clothes helped me to take my mind off of everyone else, and what girl doesn't like shopping for herself.
We perused the whole store and found a few dresses and skirts in my size that I thought were sexy, but wasn't committed to. Finally, I came upon a tan bodysuit made of sheer mesh. It was just a few shades darker than my skin tone. It was sheer enough that it would show a bit of cleavage, but still opaque enough that I wouldn't be completely on display. Finally, it had a zipper front that would allow me to show off my ample, albeit fake, chest.
"This is it!" I squealed.
"That's hot," Victoria agreed. "Why don't you go try it on?"
"Try it on?" I was confused. "I've never actually tried anything on in a store before. I've always just brought it home and hoped it would fit."
Victoria laughed. "Well, that's the benefit of being a woman. You can actually use the women's fitting rooms and see if an item fits you BEFORE you buy it. Here, let me grab a saleswoman."
She flagged down a worker who helped me into the fitting room and complimented me on my dress. I was all smiles.
I put on the bodysuit and a short black skirt that I thought would compliment it nicely. It cut to mid-thigh and had an aggressive slit up the right side. It was actually kind of slutty, but it was definitely my style. I looked at myself in the mirror and fell in love all over again. I peeked out from behind the curtain and called out to Victoria.
"Pssst, Victoria...come take a look."
She joined me in the fitting room.
"Wow! You look amazing in that. Definitely shows off a lot of leg though."
I frowned. "Is it too slutty? I was thinking about wearing some nude fishnets and a pair of shiny ankle boots with it"
Victoria pondered the outfit. "No, not TOO slutty, but it definitely shows off your goods..."
She paused.
"I'm sorry, I can't stop staring at your legs. Who would have thought my husband was hiding stems like those?"
"Shhh!" I quieted her. "Don't give me away."
I made a quick peek out of the fitting room to make sure no one was within earshot.
Victoria grimaced. "Oh my God, I'm so sorry. You look great Babe! You should totally get it."
I nodded. "I think I will get both the bodysuit and the skirt. The bodysuit is a must. If the skirt feels too short, I have some longer ones that will work as well."
I changed back into my clothes and headed over to the shoes while my wife continued to look for a dress for herself. Most of the shoes were quite exotic; neon colors and straps galore, but I was able to find what I was looking for. They were almost perfect; a glossy, patent leather ankle boot with a side zipper. The only issue was that it was a 6-inch platform. I tried them on and strutted around the store. They fit like a glove.
I heard a voice from behind me. "You absolutely have to get those."
I hastily turned to see the woman that helped me into the changing room, but was too startled to respond.
"Those look amazing on you," she continued. "They would kill with that bodysuit and skirt you picked out."
I finally built up the courage to speak. "You don't think it's too tall of a heel?"
"Girl, Hell no! You rock that 6-inch heel with your long ass legs. Go on and flaunt what you got."
I just smiled as I checked myself out in the mirror. "I think I will. Thanks for the confidence boost...I'm sorry, I didn't catch your name."
"Gianna."
"Well thank you Gianna, you have been a wonderful help today, and you have absolutely made my day."
"Of course," she added. "Us girls have to be looking out for each other, and Honey...you're gonna slay in those boots."
Gianna had sure earned that sale with all the compliments, but she also gave me a much needed confidence boost. Victoria finally returned, several dresses in hand.
She quipped, "Hey, nice shoes...wanna fuck?"
"Thanks, and yes I do," I laughed. "It looks like you've been having fun," I teased. "Whatcha got there?"
"Just a little black dress for myself, a girl can never have too many."
"I actually don't have one," I said as I shied away.
"Get the fuck out, seriously?"
I just nodded.
"Come with me," Victoria demanded as she took my hand and dragged me to the little black dress rack. "You absolutely need this dress."
She handed me a gorgeous body contouring dress that was cut to mid-thigh and had a plunging neckline that would show off ample cleavage. It was adorned with black nylon mesh sleeves and mock turtleneck all the way down to the deep V. It would hide the edges of my breastforms perfectly while still showing off my cleavage.
I just stared in wonderment. It was amazing how my wife already knew my tastes as a woman, but I guess after years of buying things for her, she just knew what I'd like for myself.
"I'm guessing you like it?" she asked.
"I love it!" I squealed as I grabbed it out of her hand and headed back to the fitting room.
As I was trying it on, a hand holding a pair of heels popped through the curtain.
"Try it with these," I heard my wife say.
She handed me a gorgeous pair of black 5-inch pumps with a thick ankle strap adorned with rhinestones. They were the ideal fuck-me-pumps to go along with the fuck-me-dress she had just picked out.
I got everything on and stepped out of the changing room. Victoria just watched in amazement as I transformed right before her eyes. Where just a few minutes before stood a scared, intimidated crossdresser, now stood a proud and commanding woman.
"How do you feel?" Victoria asked.
"Like I was born to be Ashley." I responded. "I've never felt this good in my life. I can't believe how sexy I look and feel. I think I'll go on that double date with you."
"Attagirl, let's buy you all the things and I'll set up the date for next weekend."
*************************************************************************************************************
I was on pins and needles all throughout the work week. Every minute I spent at the office I was just dying to get home and practice my voice exercises and work on my makeup with Victoria. She was a blessing; so patient and informative. With her by my side, I felt like I could conquer anything.
Friday had finally come, the day of the big double date. Victoria told me that we were going to a bar called the Social Club. It had games like pool, foosball, shuffleboard and all the like, plus a large dancefloor and a live band. I was once again a nervous wreck. It was one thing to go out shopping with my wife. Now I'd have to appear as a woman and be personable with another man. I was having second thoughts.
Victoria did her best to encourage me. "Why don't we both take half a day, come home, and just get pampered. Once we get you all dolled up I bet your nerves will settle."
"Okay," I relented. "I could use that."
I wasn't feeling much better at work. Around 11 o'clock I told everyone that I thought I had a stomach bug, and that I needed to go home. It didn't take much effort on my part to build the lie because my stomach was in knots and it was visibly obvious to anyone who glanced my way.
I got home and started with a hot, steamy shower and a refreshing full body shave. It felt amazing to be completely smooth. Victoria came home while I was lotioning up after the shower.
"Getting a head start, are we?" she mused.
"I wasn't getting anything done at work. I figured there were better things for me to do here."
"Fair enough," she relented. "Good to see you shaved your legs for your date tonight." She said with a wink.
Victoria poured us each a cocktail as we began to work on getting ready for the evening. I meticulously worked on my makeup, but still needed my wife's help with the eyeliner and eyeshadow. We decided on a similar shadowy look to last weekend, but went a little bolder with the eyeshadow. Victoria worked her magic, and it came out looking fabulous.
I shimmied into my breast forms and dressed in the bodysuit and skirt that we had picked out. I accented it with a black bra with silver metal studs that was just barely visible through the tan mesh of the bodysuit. I wore the nude fishnet stockings under the bodysuit, making sure to achieve a perfect, smooth tuck that left no indication of what actually laid in wait beneath. Having tucked away the last of my manhood, I slid the skirt into place and accented the outfit with the platform heeled boots and a wide corset belt.
Finally getting a good look at myself in the mirror, I felt rejuvenated. I decided on wearing my bold, fire engine red wig instead of the dirty blonde. I slid it on and the last of Aaron disappeared, finally revealing Ashley in all her glory. The bright red hair fell on my shoulders, highlighting the immaculate job Victoria did on my makeup.
"Holy shit!" Victoria said as she finally rejoined me in the bedroom. "You look like sex on a stick."
"What does that even mean?" I laughed.
"I don't really know, but you are definitely gonna be the talk of the club girl. Bring it in here."
Victoria gave me a sincere hug, the top of her head resting under my large fake breasts. She truly was happy for me. Now I just needed to gather the courage to get through the night.
My wife looked completely fuckable, dressed in a leather mini skirt, a dark red tank top with plunging neckline, and knee high "fuck-me-boots." She was petite yet athletic and had flawless olive skin from her latina heritage. Her 32DDs and tiny waist were on display. It was going to be hard not giving her all my attention tonight.
"I don't know how I'm supposed to focus on my date with you looking like that." I said.
"You'll be fine. Once we get settled you'll fall right in where you need to...I promise."
"Okay, just don't leave me alone with the guys."
"Of course baby," she comforted me. "You'll learn that we girls never leave anyone to go solo unless they want it. Now let's get your nails done before we head out."
I decided on a red polish to match my hair. Victoria provided a long necklace that practically went down to my navel. If I hadn't been fully covered by the bodysuit, it would have rested perfectly in my cleavage. I had decided to leave the bodysuit zipped as I was too afraid to draw attention to myself with open cleavage.
We went downstairs and waited for the boys to arrive. Right on time, Mike pulled up in a Cadillac Escalade. We waited for them to come to the door, but I couldn't help but peek out the window.
"Holy fuck, they're both huge," I gasped.
"Oh yeah," Victoria giggled. "I forgot to mention, Mike and his friend both played linebacker for Nebraska. Mike is like 6'7" and his friend looks about the same."
"Well, I guess I don't need to worry about my height so much."
I was happy, but totally intimidated. It immediately occurred to me that this was a prelude to Mike fucking my wife. She'd had big dicks before, but if Mike was only average for his build, he'd still split her in half.
We answered the door and Victoria introduced me to Mike and his friend, Teddy. Victoria informed them that I was a college friend visiting for a week from out of town. They complimented both of us, and we stood around and chatted for a few minutes before finally getting into the Escalade, Mike and Victoria in the front, Teddy and I in the 2nd row. This was it, there was no turning back now.
Fortunately, Teddy and I got along perfectly. We both had the same tastes in music and entertainment and spent much of the evening discussing the intricacies of different genres of metal, comparing which concerts we had been to and who we had yet to see. At one point, he put a hand on my thigh while we were sitting in the booth. I was stunned, but I allowed it. Victoria definitely noticed, however, as I saw her nod slightly in my direction.
Mike on the other hand was a complete tool. He thought he was God's gift to women and acted like a pompous ass. I don't care if he's as hung as Victoria claimed, I don't see how women put up with him. Victoria laughed at his ridiculous acts, but I just rolled my eyes back at her. I've watched her get fucked by other guys, but I had never met this woman before. I could not believe that she was into this guy.
The guys tried to get us out on the dance floor. I was reluctant, but after talking a lot of shit about my Foosball game, the guys challenged Victoria and I to a game for the right to a dance. Normally I could take the 2 of them by myself, but it appeared Victoria was actively working against me. At 4-4, she had an easy pass to me, but gave the ball away to Mike, easily letting him score the winning point.
"Oops, I guess we owe you two a dance, huh." She fawned ignorance, but I just glared daggers in her direction.
"Come on babe, let yourself go," she whispered in my ear. Victoria attempted to urge me onto the floor.
She dragged me by the arm out onto the floor and pressed me up against Teddy. He put his hands on my hips and I reluctantly placed one on his chest and the other on his back as we danced to a cover of Journey's "Faithfully." Fortunately, I love that song, so I gave in and tried to relax.
I must have gotten carried away in the music, because before I knew it, a wave of euphoria flowed through me. I felt completely at ease in Teddy's arms, slow dancing to 80s music. His hands on my hips electrified my body. I ran my hand down his chest, getting a good feel of his pecs and abs.
The song ended and finally snapped me out of my stupor. What the hell was I doing? The band broke into ZZ Top's "Legs," which of course Victoria said was dedicated to me. She got the attention of everyone on the dance floor and had them hooting and hollering for a show from me.
I was so embarrassed, but Teddy assisted me with a playful dance and show of my long legs, ending with a twirl and a dip. I came up a little too fast and ended up completely in his arms.
Too fast was right. I needed to slow down before I gave Teddy the wrong impression. I thanked him for the dance and for saving me from the embarrassment of being the center of attention. We went back to our booth for another round of drinks and to just chat while Mike and Victoria continued to make a scene dancing.
Teddy was actually a really cool guy and I got the feeling that if he knew me as Aaron, we would be pretty good friends. Of course I could never tell him that. I would be devastated if my secret got out. I was playing with fire as it was, leading him on the way I was on the dance floor.
The night continued much as it had without any drama. Mike continued to make obvious advances at my wife, which she gleefully took as a cue to tease him, only egging him on further. Teddy and I had a great evening, but it was getting late. That, and I had never spent more than an hour or two in heels. Dancing and clubbing all evening was taking its toll on me.
Mike drove us back to our house. We said our cordial goodbyes in the car and then we both headed toward the front door.
Just then, Teddy called out, "Ashley, hold on a minute."
I turned to see him jogging up to me. He caught up and pulled me in close, grabbing one hand in his and putting the other on my back. My free hand naturally found its way to his chest once again.
"Hey, I was just thinking. We had so much in common...and, well...I have two tickets to see Phantom of the Opera at the theater tomorrow. Would you like to go see it with me?"
I let my emotions take control of me, and without even thinking I blurted out, "That is my favorite show; I'd love to!"
That's when it happened. I was so caught up in thinking about how much I loved Phantom of the Opera, that I completely forgot that I was on a date with a man. A man who was currently embracing me. A man who had just asked me out on a second date, which I had accepted. Without me even noticing, Teddy leaned in and gave me a goodnight kiss.
It was no peck on the lips either. His tongue parted my lips and found its way into my mouth. Stunned, I just went with it. I pulled myself in closer and let him give me a proper goodnight kiss. His tongue was soft and his mouth was sweet from drinking rum and Coke all night. I closed my eyes and enjoyed being a desired woman.
Teddy slowly pulled away, our lips smacking as we parted. "Goodnight Ashley. I'll pick you up at six?"
I batted my eyes. "Sounds good Teddy. I'll see you then."
I turned and immediately saw Victoria staring at me, jaw practically on the floor. I put a hand to my lips and gave her a cheeky grin.
"What was that?" She demanded.
"I...I don't know what came over me. He caught me off guard with the show tickets, and...and I couldn't say no to Phantom of the Opera. Before I knew what was happening, we were making out. I couldn't stop him without giving myself away."
Victoria just smirked. "Well, you look like you enjoyed it."
"I have to admit, I didn't not like it," I shrugged. "But what am I gonna do now? Now I have to go on a real date with Teddy."
"Babe, this was a real date. Now you're going on a second date." Victoria laughed.
"Well I was never expecting to see him again." I explained nervously.
"Don't worry," Victoria calmed my nerves. "It's just a second date. He won't expect anything more than another Goodnight kiss. Besides, what a perfect opportunity for you to bust out that new little black dress and put some mileage on it."
With that done, we made our way to bed. We undressed, but I stayed as Ashley. I would have thought that I would be horny for Victoria, but I couldn't get my mind off Teddy. My wife cuddled with me as we drifted off to sleep, but deep in the recesses of my brain, part of me wished that it was Teddy cuddling me in bed and not Victoria.
The next afternoon went by in a blur. I couldn't wait to see the play, but I was more nervous than I had even been the night before. Victoria offered her help getting ready, but I decided to take the challenge on my own.
"Aww, my little girl's all growns up," she teased, mocking my love for the movie Swingers. "I'll be just downstairs if you need me."
I prepared for the evening much like the previous day; shower, full hair removal, lotion, makeup, eyelashes, breast plate, wig, nails. It took some time, but the result was stunning. Teddy was in for a treat tonight.
I began to put on the mesh and polyester blend bodycon dress, but realized I was going out, and I should wear some kind of undergarment. All I had was lingerie though. I went with a black lace bra, panty, and garter set and a pair of 5 denier, black Marilyn stockings. They were so sheer, they were barely there. I topped off the look with a silver necklace, a few bracelets, and then finally put on the 5-inch pumps with the ankle straps.
Finally, I joined Victoria on the couch in the living room.
"Well look at you. You look amazing." She complimented me. "That little black dress is gonna bring Teddy to his knees."
"I'm just hoping to get through the night," I confessed. "What if he tries to make a move?"
"You'll be fine. Just be honest with him. He's a good guy. He won't go farther than you let him...and if you need me, I'll be right here and just a phone call away."
"Really?" I asked. "I figured you would be setting up a vitamin D injection with Mike."
"Cute," she giggled. "But no, I didn't want you to be worrying about me while on your date with Teddy."
Just then, Teddy pulled up and came to the door. I didn't know what I expected, but I was stunned by his look. He looked very dapper in charcoal slacks, a pinstripe button up, and a charcoal vest. He greeted me at the door with a small kiss.
"Ashley...wow! You look...amazing!" He gushed.
"Thank you, you clean up pretty well yourself," I replied bashful.
From the couch, Victoria yelled out, "You too kids have fun tonight, but don't keep her out all night, you hear Teddy."
Teddy laughed, "Yes Miss Victoria, I'll have Ashley back at a reasonable hour."
He then grabbed my arm and led me to the car, opening the passenger door of his BMW 7-Series before joining on the driver side.
"Wow, nice ride." I complimented.
"Thanks, I'm actually more of an American Muscle car guy, myself, but I just fell in love with the 7-series. It's comfortable and handles great."
"I actually owned a Trans Am in my younger days," I laughed.
"Of course you did, Ashley. You seem to be right in line with everything I like." He said, almost dumbfounded.
The night continued in this fashion. We laughed and recounted all our likes and dislikes, sometimes almost seeming like we had the same childhood. I left out the part where I used to play football up through high school.
Teddy truly made the night enjoyable and put me at ease from the start. It felt natural to be out and about as Ashley, and despite my initial hesitation, was perfectly happy being on a date with this man.
The show was incredible. I had seen it on TV and in the movie theater, but I had always wanted to see it performed live. The Phantom and Carlotta were really good, but the actress playing Christine Daaé was amazing. Everytime she sang, I found myself gripping Teddy's leg. The performance was very moving and emotional and really had me embracing my life as Ashley.
Teddy held my hand as we left the theater and walked back to the car. I was so comfortable that I actually placed my arm in his and laid my head on his arm as we waited for the valet. I looked up at him and just smiled.
"Thank you so much for taking me to see Phantom. It was even better than I could have ever imagined."
Teddy smiled back, "Thank you for joining me and being the prettiest girl in the theater."
I blushed and shied away, but inside I was bursting with joy. I was so overwhelmed with happiness, that I accidentally let my guard down and let my true feelings show.
"I don't want this night to end," I whispered.
I didn't mean for Teddy to hear, but apparently I was louder than I thought.
He answered, "Well, would you like to come back to my place for a drink?"
Shit! Did he just ask me to come over? I am so not ready for that.
"Um...well, I guess..." I stuttered.
Teddy interrupted and saved me from answering. "You don't have to. Was just a thought. I really like spending time with you and I don't want the night to end either...but I don't want you to do anything you're not comfortable with."
I thought about it for a minute. What was I so afraid of? He is a nice guy and he likes me for who I am, and he clearly respects my boundaries. I was so nervous. My stomach was in knots, but I really liked him and wanted to spend more time with him.
"No, I'm ok. I'd love to join you for a drink. Thank you." I consented.
We got back in his BMW and headed to his condo in the city. It was a gorgeous place with an incredible view, but as I sat on his couch while he went to make me a vodka tonic, I couldn't help but think how crazy this all was. Just a week ago I was a closeted crossdresser who had been caught in the act by his wife. Now, I was on a second date with an amazing man and waiting for him to join me for drinks in his living room.
Teddy sat next to me on the sofa and we enjoyed our drinks while talking about the show. I actually felt at ease and got in close and placed a hand on his leg as we chatted.
Then, without warning, Teddy leaned in and gave me another kiss. Again I was caught off guard and initially pulled away.
"I'm sorry," Teddy apologized. "I got carried away with the moment."
I felt bad. I actually wanted him to kiss me, I just wasn't used to being kissed by a man yet.
This time I caught Teddy off guard. I placed a hand behind his head and pulled him back in to continue the kiss. I bit and sucked on his bottom lip, reveling in how soft and sweet it was. After teasing him in that manner for a minute or so, I plunged my tongue into his mouth and massaged his with my own. I wanted this man, and I wanted him now.
Teddy responded with his hands, caressing my curves from breasts to hips. I let out a slight moan into his mouth as I continued to probe with my tongue. He took that as a cue to be more aggressive with his advances. This time I welcomed it. Teddy wrapped his big arms around me and pulled me close.
We explored each other's hard bodies with our hands while making out on the sofa. His hands fondled the underside of my breasts and gripped at my back. I ran my fingernails down his clothed back, desperate to feel my hands on his skin.
I put both hands on his shoulders and pushed him back as I finally pulled my mouth away from his. Teddy looked at me, confused at why I had now pulled away, but the look in my eyes was that of pure desire. I quickly slid my hands to the buttons of his vest and shirt, fumbling to get them open with my long painted nails.
I finally got his shirt open and dove in with both hands, clawing at his hard, smooth pecs. I had felt them already several times above his clothes, but now that I had unencumbered access, I held nothing back. I cupped both pecs with my soft hands and dug my nails into his chest, leaving tiny indentations in his skin. I was in awe of how small my hands looked against his body.
I broke out of my trance and looked Teddy in the eyes as I stalked him like a wild animal. Teddy laid back and allowed me to take control as I pushed him back against the armrest of the sofa. The hemline of my dress rose and showed off the lace tops of my stockings as I straddled his body and crawled my way up his chest.
Teddy's abs twitched as I brought my lips to his skin just above his belly button. I traced the distance along his abs all the way to his left nipple with my tongue before finally taking his nipple in my mouth. I continued to concentrate my attention to his pecs, playing with his nipples in my mouth and grasping at them with my hands.
Finally, I made my way north and nibbled on Teddy's neck, inhaling his scent as I did everything in my power to turn him to putty in my hands. I didn't plan on going this far, but it was like there was an unseen force controlling my actions. I couldn't stop as I dove back into Teddy's lips, letting him explore my mouth with his tongue.
Teddy grunted as I rubbed my perfectly tucked and panty covered cock against the length of his hardening dick. He grabbed my ass with both hands and started to pull my dress up over my hips. I finally panicked and grabbed both of his hands with mine before he exposed my secret. I needed to retake control and focus Teddy's attention elsewhere.
I really shouldn't have let it get this far to begin with, but I could hardly control my own actions. It was just supposed to be a drink before heading back to Victoria, but now I had Teddy half naked and on the verge of undressing me. What I did next would have serious consequences.
For what seemed like an eternity, I sat there, both of my hands gripping Teddy's wrists as he held onto the hem of my dress. Unsure of what to do, I just stared into his eyes. I was sure he could see how scared I was and for the first time since we met, I felt like he knew my secret. I didn't want to stop, but I also couldn't let him expose me.
Finally, I lifted his arms and pinned them above his head. I kissed his lips and traced my way down his body in reverse, kissing every inch of his body as I made my way toward the waistband of his pants. My bright red hair was scattered across his tanned chest as I lifted his waistband and left red lipstick on his pelvis, just above the band to his boxer briefs.
I flung my hair back over my left shoulder as I once again looked Teddy in the eyes while undoing his belt and the zipper to his pants. Teddy panted in anticipation as I ran my hands along his thighs. There was no turning back now. I was about to cross several lines and had no qualms about doing so.
I could sense that Teddy was big, at least significantly bigger than me as I felt around his groin and saw the growth in his pants. I pulled his pants down and rubbed Teddy's cock through his briefs while continuing to kiss along the waistband. Finally, I dug a fingernail under the waistband, allowing his erect penis to spring free towards his belly button. He had to be around 8 inches long, and a healthy girth. Not skinny, but also not intimidatingly thick.
I let my lips move across the purple head of his now exposed cock. The sensation was overwhelming. I licked my lips and let them glide up and down the exposed part of his glans before closing them with a smack as I came off the tip. Teddy moaned in pleasure as he placed a hand on the back of my head, encouraging me to go further.
Not long ago I would have been disgusted by my actions, but in the moment, I did not need the encouragement from Teddy, but I did welcome it. I went with the momentum and pulled down the rest of Teddy's briefs, finally exposing the full length of his cock. I was hypnotized by the sight of it. It was beautiful as it seemed to glow in the soft light, like a beacon guiding my lips to find a home at the end of its length.
I admired Teddy's cock as I lightly traced it from balls to head with my fingernail, drawing a moan and a shudder from Teddy. After teasing for a few moments longer, I took the base of the shaft in my right hand and massaged my thumb against his glans.
Again, I marveled at his size. Having only held my own five inch and change cock in my hand, Teddy's dick looked massive in comparison. I licked my lips and brought my head to the tip of his penis, allowing the head to ever so slightly part my lips and penetrate my mouth. I moved my head lower, taking the entirety of the head of his cock into my mouth.
Subconsciously, I moaned as I got my first real taste of a man's cock. I wasn't disappointed. Teddy filled my mouth and I savored the feel of every ridge and vein with my tongue. I worked my way up and down the first few inches of Teddy's length with my mouth while working the bottom half of his shaft with my hand.
"Oh my God!" Teddy whispered under his breath. "Your lips are amazing. You're such a good little cocksucker."
I slurped off the tip of his cock leaving a trail of saliva attached to my bottom lip and gave Teddy a devilish grin.
"I'm just getting started," I said in a breathy voice.
Some force had possessed me and taken over my body. Teddy's cock in my mouth was the only thing that could quench my desire. I returned my focus to his dick and attacked it with a ferocity I had never experienced. I didn't just want to give Teddy a great blowjob, I wanted to give him the best blowjob of his life. I wanted every future blowjob to be compared to this one.
Teddy thrusted his hips in time with my head as I bobbed up and down on cock, slurping and slobbering down his entire length. I used both hands to massage his thick shaft and then massaged his heavy balls to encourage him to push his cock deeper into my mouth.
The head of his dick hit the back of my throat. At first I felt like I was going to choke, but I fought back the tears and the queasy feeling and continued my work on the head. Teddy thrust again and again, repeatedly hitting my gag reflex. I couldn't take much more. I was going to lose it.
Tears started to leak from the corners of my eyes, ever so slightly ruining my eyeliner. I pulled my mouth off of his dick, gathered a breath, and plunged Teddy's cock as far into my throat as I could bear. He slid past my gag reflex as I swallowed him up, inch by inch. My throat burned as it was invaded and stretched by his thick, stiff rod.
My lips almost reached the base of his shaft before my momentum stopped, leaving a large lump in my throat in the shape of a cock. I pulled off and gathered my breath while I continued to stroke the massive snake with my hands. Then I returned for more, burying that cock back into my throat, taking as much punishment as I could bear.
Rapidly, I moved my head up and down as Teddy pumped his hips into my face. I opened my mouth and my throat as wide as I could manage. Teddy gripped my head with both hands and forced his dick the rest of the way, slamming my nose into his pelvis. The pain shot through my nose and into my skull, causing more tears to break free, smearing my makeup.
Teddy continued to pound away as I gagged on his cock, spit flying from my nose and mouth. He had his way with me, using my mouth and throat as his personal fuck toy. I loved every minute of it.
I wanted to please him. I wanted him to fill my stomach with his cum. I wanted to be his personal receptacle. Teddy obliged. His thrusts came faster and faster, his chest rising and falling as his breaths became more labored. He was reaching the point of no return.
I grabbed both of his ass cheeks with my hands and squeezed while pulling Teddy as deep into my throat as possible. Finally, Teddy's muscled legs stiffened as he rewarded my throat with stream after stream of hot, sticky cum.
I continued to bob my head up and down to match his spurts, tonguing his balls every time a bottomed out. Teddy pumped at least seven streams of cum into my belly, completely filling me and soothing my throat as I finally pulled off his cock.
"Ohhhhh Fuuuuuuuuck! Ho-Ly shit!" He exclaimed. "Ugh, ugh, ugh."
Teddy grunted with every spurt until I had swallowed every last drop of cum he had to offer me. He continued to moan and arch his back as I proceeded to clean his dick with my tongue, making sure to tease the underside of his head with my tongue. Teddy squirmed with pleasure as I refused to let go of his manhood.
Finally, I had my fill and granted him relief as I set his dick free from my mouth.
Teddy threw his head back and gasped, "Oh my God. That was amazing. How...how did you do that?"
Confused, I looked at him with a slight frown. "How did I do what?"
"How did you make me cum so much? I have...I have never cum so hard or so long." Teddy said between rapid breaths.
I didn't want to tell him that it was my first blowjob, but I was super proud of my efforts. It was the best compliment I could receive.
"I guess I just know my way around a nice dick," I claimed.
I immediately regretted my choice of words. It made me sound like a slut. I didn't want him to know it was my first blowjob, but I also didn't want him thinking I would suck anything with a dick.
I tried to walk back my words. "I haven't been around many, but your cock really got me worked up. It deserved my best effort."
Teddy agreed. "Well, that was the best blowjob I've ever had. I have never face fucked anyone like that. It was incredible."
I didn't know how to respond. I was just so happy that he enjoyed my performance and had such a memorable experience. I wanted more but decided it was probably best to stop while I was ahead, although I had not felt desire like this in quite some time, and never in my wildest imaginations would I ever have thought that I could have these feelings for a man.
I grabbed some water from the end table and then stood and straightened out my dress.
"Well, that was really fun, but I should probably start heading back home. I don't want Victoria to worry." I claimed.
"Are you sure I can't repay the favor?" Teddy offered.
"Oh, thank you, but as much as I'd like to...and believe me, it's killing me to say no, but I really should be going."
I wanted so bad for Teddy to fuck me and make me a real woman, but I knew that I'd have to tell him the truth, and then who knew what would happen.
"Okay, because I am more than willing to take care of your needs if you wanted. I'm not trying to pressure you, and we definitely don't have to have sex...but I'd like to try to do for you what you did for me. If you'd let me, of course."
I thought long and hard on it. Really long and hard...just like his dick...that I wanted inside me.
"I...I would love to...but, um." I bit my lip to stop myself from talking.
"But what? Is everything okay?" Teddy reached for my hand and seemed genuinely concerned for me.
Oh fuck. I had to tell him. Come whatever may, but I needed to see where this was going. I needed to see it through to the end, just in case there was a chance he was accepting.
I sat back down on the sofa next to Teddy. "Um, well...I guess there's something I need to tell you. I don't really know how to say this, but here goes."
Teddy put a hand to my leg to reassure me, but then he cut me off and spoke.
"Ashley, I know what you're going to say, and I appreciate you coming out to tell me, but I already know. Victoria told Mike and I last week. I know you're a crossdresser."
I just sat there stunned as Teddy continued.
"At first I was hesitant to go on the double date with Mike, but Victoria shared a picture of you shopping for your outfit for the date, and I must say, I was blown away by how stunning you were. I knew I just had to meet you, so I agreed to go on the date, but Victoria made Mike and I promise not to let you know that we knew your secret."
I couldn't believe it. I was so embarrassed. "I can't believe you both knew the entire time."
I hid my face in shame, but Teddy lifted my chin to look at him.
"Ashley, to be completely honest, if I hadn't known beforehand, I wouldn't have known until you told me. But I'm really glad you did. It was killing me keeping it from you."
I was still in shock and embarrassed. "I can't believe my wife did that to me. What else did she hide from me?"
"Well, since you brought it up," Teddy frowned, "Victoria was the one who gave me the tickets to the show tonight. She told me that if I wanted a second date that you wouldn't resist a live showing of Phantom of the Opera."
My wife had completely played me. I did not know how to process this new information. Should I be furious with Victoria or thankful that she made this evening possible? I was literally shaking from my nerves. I did not expect my confession to play out in this manner.
Teddy placed one of my hands in both of his. "Ashley, there's no reason to be upset. I really like you, and everything else has been completely honest. I just didn't want to let the opportunity to spend more time with you to slip away without trying, so I took up Victoria on her offer. But if you want to leave, I understand and I'll take you home."
I was on the verge of tears. My wife betrayed my trust, but she also seemed to know me better than I did myself. If I was being completely honest with myself, I wasn't upset with Teddy; I was more embarrassed that Mike knew who I was the entire time he was being so blatantly forward with my wife.
As my mind raced with fears and wild imaginations, Teddy remained a rock, focused on trying to calm rapid breathing. Just then, he took a calculated risk. He pulled me close and passionately kissed me on the lips as he caressed my face with both hands.
I melted into his arms and let all my tension flow back into him. It was a risky move on his part, but it had worked. My mind slowly focused on returning his passion instead of worrying about the past.
Teddy broke the kiss and said, "See, would I have done that if I didn't truly want to be with you?"
"I guess not," I relented.
He stood and took my hand. "Come on, I'll take you home."
Now it was my turn to take a risk.
"No, I think I'll stay a bit longer," I said through a widening grin.
I sat down on the large circular ottoman and pulled Teddy back down on top of me. He softly landed on me, between my spread legs, his face landing on my fake but soft DD breasts.
Teddy didn't take long to welcome my invitation. He took control and instantly it felt like there were at least a dozen hands all over my body. He squeezed and caressed my breasts through my dress, his hands felt my hips and thighs. I felt him grab a handful of my ass. I was in heaven.
Teddy had pulled his boxers back up, but his pants still hung at his knees. He popped off of me and quickly removed them before grabbing the hem of my dress and pulling it up over my hips. This time I let him. He exposed my garter belt and stocking tops and then placed his hand on my panty clad crotch.
I was still tucked away securely, but his touch made my loins burn with a heat I had never felt. I wanted this man to fuck my brains out. I pulled him back down on top of me. His bulge pressed into me. I brought his head to mine and whispered into his ear.
"I want you to fuck me, Teddy. Make me a real woman. Make me your bitch."
He sprung into action. Teddy pinned my hands above my head by my wrists and continued to grind his thick bulge into my crotch. I bucked my hips back to meet his thrusts.
"Oh fuck...yes!" I moaned.
Teddy released my hands to pull off his boxer briefs, again setting his massive cock free from its enclosure. I couldn't wait to feel its weight on me. He placed his dick on my still flaccid and tucked cock, only separated by a thin layer of silk and nylon mesh. Teddy grabbed my hips and pressed himself into me.
The feeling was incredible. Teddy pulled my dress even higher, exposing me up to my belly button. I held my dress in place as he attacked my body with his tongue. He licked all my curves as he sucked and caressed my body, but only teased my crotch with light breaths and faint touches. I wanted to shove myself into his mouth.
At last Teddy rose from my body and concluded his teasing.
"Turn over and get on your knees," he ordered.
I did as he commanded, eager for him to reward my obedience with his beautiful cock. I slowly turned myself over and arched my back as I raised my ass in his direction, keeping my face and breasts pressed to the sofa.
"Just like a pornstar. I knew you were a filthy girl." He complimented me.
Teddy caressed my ass and ran his hands down my stocking clad legs. He put both hands between my legs at my thighs and slowly pushed apart.
"That a girl, spread those legs for me."
I did as he ordered. I needed him to satisfy the fire inside me.
Teddy grabbed my thong and pulled it to the side, careful to leave me still tucked away. Then I felt him press his heavy dick against my hole. I let out a huge sigh of relief. He had yet to penetrate me, but the feeling was spectacular.
He lubed up the head and pressed himself up against my opening but I instinctively pulled away.
Teddy grabbed my hips and eased me back. "Nah, nah, nah...come back here you."
I inched my way back towards Teddy's erect dick, nestling it between my buttcheeks before I stopped and inhaled a deep breath. Teddy leaned into me, pressing the head of his cock into my ass. The pressure was immense. It was not so much painful, but it was uncomfortable...at first. My breathing increased rapidly as I got used to the intruder.
Teddy didn't press any further, but he held me in place by my hips, preventing me from squirming away again. Once my breathing returned to normal, he increased the pressure and popped the bulbous head past my sphincter and into my ass.
I let out a sound that could only be classified as half moan and half scream. I wanted so bad to continue, but the pressure was greater than anything I had ever felt. It seemed like he was going to rip me in half.
"Stop, stop...you have to take it out." I begged.
Teddy placed a hand on my back. "Just take a deep breath and try to relax. It will slide right in once you calm down," he urged.
I closed my eyes and took methodical deep breaths.
In.
Out.
In.
Out.
I finally felt the muscles in my legs and back loosen. Just as I had gotten used to the pressure in my ass, Teddy leaned forward and the entirety of his length disappeared inside me.
"Ohhhhh fuuuuuuck!" I moaned.
Teddy laughed, "I know, right."
His cock was heavenly and he just left it buried in me to the hilt. I turned my head to look at Teddy and saw the most amazing view.
He was kneeling upright behind me, his firm chest out proud as he mounted his conquest, dick fully inserted into my virgin ass. He slowly pulled back, revealing his thick, veiny cock inch by inch until only the head remained inside.
The feeling of being emptied left a void inside that I now needed filled. Teddy paused a second, waited for me to push back, and then finally thrust himself back inside me until his thighs slapped against mine.
"Mmmmm," I moaned. "Oh my God, you feel so good inside me." I was practically crying out in pleasure.
Teddy picked up the pace. At first, his thrusts drove me away as the pressure increased, but once I got used to the rhythm, I met each of his thrusts with one of my own.
Our thighs slapping provided the beat to our sexual dance. I felt Teddy's massive balls slapping into my tucked cock. I turned and admired the sight of this Adonis making love to his woman. Teddy's abs rippled with every thrust, dripping with sweat. He had a firm grip on my garter belt and pulled me back into him in a rhythmic motion.
He began to grunt with every thrust of his massive cock. I could tell he was getting close.
I urged him on. "Cum inside me Teddy. I need to feel your cum fill me up. Please! Please! Cum in my ass!"
He increased his pace to something ungodly fast. I didn't know it was even possible to fuck that fast and hard. Teddy's balls slamming into my flaccid cock had me on the verge of cumming myself. I could no longer keep myself propped up on my elbows.
I moaned like a bitch in heat as my chest fell to the sofa. "Oh! Oh! Oh! Ooooooh yes!"
I reached a hand between my legs and rubbed my small cock. Holy shit! I was going to cum.
I spasmed as I came. My legs quivered and my whole body shook. I screamed "Teddy" as cum dribbled from my tucked cock and coated Teddy's dick as he continued to pound me into submission. I came for what felt like minutes when I finally felt Teddy's balls flex and his legs stiffen.
He gave me one last thrust and buried his dick in my ass as deep as it would go. Teddy grunted and let out torrent after torrent of cum into my depths. He filled every last inch of me with his cum until it had no place else to go except to erupt from inside me with a loud "splurt!"
Teddy collapsed onto my back, letting his cock slip from inside me and rest against my panty and cum covered crotch. He breathed hard as he buried his head in my neck and took in my scent.
"That...was...incredible," he got out between labored breaths.
I reached behind with my free arm and held his head close to mine. I had never in my life had such intense and passionate sex. I didn't want to let him go. Not even sex my gorgeous wife compared to what I had just experienced.
My transformation into Ashley was complete. I no longer wanted to be Aaron. I wanted to live my life as Ashley and I wanted Teddy to have me whenever he wanted.
As my head began to clear from its euphoric haze, the weight of what I had done finally hit me. My wife had set me up on this date, but I had still been unfaithful without discussing it with her first. Besides, it's not like I could get what Teddy gave me from her, so was it really cheating? Just to be safe, I had better get heading home and try to sneak in quietly.
I was still enjoying the weight of Teddy's body smothering mine, however, and was reluctant to break the embrace. Just then, unexpectedly, the front door flung open and in walked Mike. I just stared at him wide eyed, once again feeling like a deer in headlights.
"Holy shit, Teddy." Mike chuckled. "I can't believe you got that bitch to fuck you."
"Teddy!" I squealed. "What is Mike doing here?"
"He lives here." Teddy stated matter-of-factly. "He's my roommate. I thought you knew. I told him you were coming over and he headed out."
"Actually," Mike corrected. "I just came from your house Ashley. I showed your wife what it feels like to be fucked by a real dick, but from the looks of it, Teddy showed you the same. Hahaha."
Mike gloated in his newfound dominance over me. I couldn't believe Victoria fucked him when she said she was going to spend the night alone. I felt betrayed, and yet at the same time ashamed that I had done the same to her. I hung my head in shame as I stood and began to clean the evidence of my infidelity from my body.
Teddy helped me with a towel and handed me my things. "Come on Ashley, I'll drive you home."
I thanked him and was glad that he was such a gentleman compared to Mike. I definitely got the better of the two, no matter how hung Mike actually was.
Teddy helped me to rush out the door, but that didn't stop Mike from getting in one last dig at my expense.
"Hey Ashley," he hollered from across the room. "Next time I fuck your wife, why don't you tag along. I'd love to fuck both you bitches back to back. You know, to see which of you is the better lay."
I ignored his jab as I walked out of the condo, but in the background I heard him laughing at his own joke.
Teddy helped usher me to his car. "Don't listen to Mike. He can be an ass sometimes. I had a really great night. I would really like to see you again sometime if that's alright with you?"
I was still stunned by the turn of events. "I would too, but I think I need to talk some things over with Victoria before that happens."
"I understand that," Teddy agreed.
Unfortunately the ride home was mostly quiet and awkward. Doing the walk of shame with the man who notched me on his bed post was uncomfortable, no matter how much I enjoyed his presence.
We pulled up to my house. It was mostly dark, save for the light in the front window. That was good news. Hopefully Victoria was already asleep and I could sneak in and clean up without her seeing my walk of shame.
I thanked Teddy for an amazing evening and gave him a goodnight kiss appropriate for his performance.
"Goodnight Teddy. Tonight was probably one of the best nights of my life. I'd love to see you again too. Call anytime."
During the silence of the drive I decided that I would deal with the consequences of my actions from Victoria, but no matter what happened, I definitely wanted to spend more time with Teddy. Hopefully, he would give me another good fucking as well, but for now, I had to focus on getting into my house quietly.
Teddy walked me to the door and I gave him another kiss goodbye. He walked back to the car and I slowly entered the house, careful to make as little noise as possible. It was dark, but it seemed as though Victoria was upstairs and hopefully asleep.
I took off my heels and began to creep up the stairs when the light in the living room flickered on.
Victoria called out to me, "Are you just getting home now?"
"Um, yes," I swallowed hard.
"Well come sit by me. Tell me how the show went? You must have gone out afterward, huh?" She didn't seem bothered by my appearance or late arrival.
"Yeah, something like that." I said as I joined her on the couch.
Victoria was still in her yoga pants and tank top. If she had just fucked Mike, she didn't look the part. At least not like me, hair a mess, makeup destroyed, dress disheveled and likely covered in cum in places I couldn't find.
"Oh my God, what happened to you?" Victoria gasped as she finally saw my appearance.
Then it finally dawned on her. Her hand flew to her mouth as she covered her gaping expression.
"You didn't? You did! Oh my God, you fucked him didn't you?" Her tone varied with each sentence, emphasizing each word.
I just nodded in shame.
Victoria completely caught me off guard. She pulled me in for a hug.
"Get in here." She said. "I'm so proud of you for embracing Ashley. I mean...I can't believe you actually did it, but I'm so happy for you!"
"Thanks, I guess," I stuttered. "You mean you're not upset?"
"Of course not!" She consoled me. "I actually hoped you would go home with him, I just didn't expect it. I guess that explains why Mike dropped by unexpectedly. Teddy must have kicked him out of the condo."
"Yeah, about that." I confronted her. "I didn't know they lived together. Mike walked in on us post-coitus. He definitely got an eyeful and he definitely made a point to let me know that you two had spent the night fucking."
"Oh what a fucking liar." Victoria steamed. "He came over expecting to fuck but I sent him home. I didn't want you to come home to that if you called it a night early."
"Oh, I see." I felt terrible. "Well, he told me that the next time he fucks you, that he wants me to join in so he can see who is the better lay. I really don't know what you see in that guy."
"Yeah, you're probably right. I think I should leave him wanting. Teddy seems great though. Are you gonna tell me all about your first time?"
I stayed up recalling the evening with Victoria on the couch. She hung on my every word and was thrilled to hear me tell her every detail about losing my virginity as Ashley, and she was definitely impressed by my descriptions of Teddy.
"Ashley," she said endearingly, "I am just so happy that this happened for you. I don't exactly know what this means for us, but I just want you to know that I support you, no matter what happens."
I thanked her and embraced her for her caring and concern.
"I love you Victoria. You are still the love of my life, but I really enjoy the part of me that is Ashley. Maybe, if you're up for it, and I can convince him, we can have Teddy over and we can both have him? I'd really like to hang that over Mike." I said as a devious grin spread across my face.
Victoria returned the look. "I think that sounds like a great idea!"