*****All characters in the story are 18 years of age or older*****
My phone buzzes and I give it a brief glance out of habit.
"Holy shit, it's Jason." I say aloud.
And it's not just a text, he's actually calling me. I reach to grab the glowing device, but hold it at a distance as if it were a venomous snake. I never expected to hear from him again. Maybe it was an accident. In the decade of our friendship, I do not think he has ever actually called me. Should I just let it go or do I actually answer?
Jason has been my best friend practically my entire life. We met in First Grade, and up until this year, we have had most of our classes together. This past summer, right before our Senior year, his family moved a few towns over. Now, for the first time since I can remember, I started a school year without my best friend.
Fortunately, we are only about 30 minutes from each other, and even though he now goes to a rival school, we still hang out when we can. In fact, it normally wouldn't seem out of place at all for Jason to be messaging me at any time of day, but after last weekend, I never expected to hear from him again.
On Friday after school, I went over to his house and went with him to a party thrown by one of his friends from his new school. At some point in the evening, some girl confused me with another one of her girlfriends. Normally, not a problem, but once I told her that I wasn't the girl she was looking for, she exploded in laughter and made a huge deal about how much I looked like a girl.
My long hair and waifish looks made me the butt of all their jokes. It was probably just the alcohol flowing, but soon all the guys were pinching my ass and pretending to hit on me. The fact that I was from a rival school seemed to encourage the behavior even more. Jason didn't join in the mockery, but he couldn't exactly stand up for me either without being ridiculed himself. I turned to a bottle of Vodka and tried to numb the embarrassment.
The liquor didn't exactly help in that respect, but it did help to loosen my tongue. After the party, I stayed the night at Jason's house, not wanting to drive back home after drinking. We chatted a bit and he apologized for not having my back at the party. I told him not to worry about it, and that I understood why he couldn't, but I didn't think that I'd be going to anymore of his school parties. He agreed and we laughed, but then he said something that I now realize was a joke, but my drunk mind took it as something else.
He said, "Allen, you do have to admit though, you have a very pinchable ass."
For some reason I took that as a cue to confess to my best friend that I had been a closeted crossdresser for years. I told him that I liked to steal items from my older sister, and that I actually looked really good in her old cheerleader's uniform, leotard, pantyhose and all.
Unfortunately I had completely misread the room. When I was met with silence, I panicked and pulled up a picture of me in the aforementioned uniform on my phone and showed it to Jason.
"Why are you telling me this?" He asked, thoroughly confused.
"Um...honestly, I don't know," I said. "I guess it's the vodka and all the attention on my ass today."
Quickly, I tried to reverse course, but it was too late. The damage had been done. The awkwardness was unbearable. I woke up before Jason and snuck out, saying a quick bye to his mom as I rushed out the door.
All week I couldn't stop thinking about how stupid I was. What if he told our other friends? I couldn't believe what I had done. I had not heard from Jason since and never expected to hear from him again, but now he's calling me on the phone.
I finally slid the green icon to answer just before it went to voicemail and slowly brought the phone to my ear.
"Ummm...hello?" I practically whispered.
"Hey, uh...Al...it's...Jason."
This time my tongue was frozen. The lack of alcohol had rendered me speechless.
Jason continued, "Actually, it's probably better if I just talk...Oh man, how do I say this? I actually rehearsed it three times, but now I don't know how to start."
I knew what was coming and I was prepared to hear it. "Just say what you have to say, bro."
"Okay, here it goes. I don't know why you told me what you did last week, but I haven't been able to stop thinking about it."
"Yeah, me too," I interrupted.
"No, I mean I haven't been able to get that picture of you in that cheerleading uniform out of my head. You were...well you were right, you did look really good in it. I...I can't stop thinking about your legs."
I was completely floored. I was expecting him to tell me to never talk to him again.
Jason struggled to find the words, "I guess what I'm trying to say is, well, I wouldn't mind seeing it again."
"The picture, you mean?" I asked.
"No...well, yeah but," he stuttered. "What I mean is, I wouldn't mind seeing more of you like that."
"You want to see me in my sister's cheerleading uniform?" I asked, completely blown away at the turn of events.
Jason finally found the courage he was hoping to summon. "Yes, but I was wondering if you just dressed like that for fun around the house, or do you ever go out like that?"
I let out a small laugh. "No, I've never been out of the house in my sister's clothes. I can't even believe I told you, let alone showed you the evidence."
"Would you?" He asked.
"Like, would I wear it for you?" I questioned.
"No, would you go out in public as a girl?"
I had never really thought about it. I loved dressing up and I loved the way women's clothes and makeup made me feel. I had to admit, I could pull off a pretty convincing girl.
"I had never really considered it, but in the right circumstance, yes. At least I think I would."
Jason let out a sigh of relief. "Good, okay...um, well then can I ask you another question?"
Finally relaxing a bit, I said, "Sure...go ahead."
"Well, would you consider going to Sandberg's Homecoming with me as a girl? It's in two weeks, and I thought I had a date, but she bailed on me last minute."
I practically gasped, "You want me to be your homecoming date?"
He was hurt by my response, but in my defense, I couldn't believe what I was hearing.
"No, not like that. But, I'm embarrassed to go by myself and I don't want to not go to my Senior year homecoming. I just thought, you're my best friend, and I know we'd have a good time. You opened up to me and I didn't know how to respond, but if you'd let me, I'd like to see more."
I didn't know how to respond, but the prospect of getting to dress up in a sexy dress and show myself off had my mind flooding with ideas. I knew I wouldn't be able to say no.
"Please say something," Jason begged.
"I would be happy to." I finally said. "I have no idea where to begin or how we're going to pull this off without either of our parents finding out, but yes. I would like to try."
The rest of the conversation was a blur, but we decided that I'd tell my parents that I'd be taking a girl from his school to their homecoming and that I would be staying at Jason's house that night. I still didn't know where I would get ready for the evening, but Jason said he'd take care of it and that he would let me know. I just had to focus on getting an outfit put together.
Over the next two weeks, the initial excitement that I felt slowly morphed into nervous tension. What if the students from Sandberg recognized me? Maybe this was all just a prank to continue their earlier hazing of me. Jason did his best to calm my fears, but I was still hurt from that party and afraid of what might come at the dance.
It took a lot of convincing on his part, but I finally sent Jason a few pictures of me dressed as a girl, including the picture in the cheerleader's uniform that started all of this. In reality, him asking for a few pictures should have made me more nervous, but for some reason it really helped to put me at ease.
I took some money that I had been saving for some upgrades to my car and went dress shopping. I had bought small things here and there, like nylon stockings and jewelry in person, but I had never actually shopped for an outfit. I headed to a dress shop out of town, fortunately it was closer to Sandberg than it was my school, so it was not very likely that I would run into anyone I knew.
The woman working the store was very understanding and I was very upfront about my situation. My heart was pounding through my chest, and I felt like she could hear the terror in my voice, but I told the woman that I was transgender and that I was in need of a Homecoming dress. She practically squealed with glee and introduced herself as Claire.
Claire honestly seemed more excited about helping me find a dress than I was about getting to try on all the pretty clothes. She helped me relax and brought out a few items that she felt went best with my complexion.
At 18 years old and having never really been into sports, I really am quite diminutive and demure. I'm 5'6" and at only 130 pounds, I have a tiny waist, small shoulders, and as the students of Sanberg recently discovered, tend to carry a bit of plumpness in my buttocks and have womanly hips. My skin is tanned, not quite bronzed, but I do work outside in the summer, so I've held onto a bit of color. My hair is a wavy shoulder-length brown with natural blonde highlights, also a product of working in the sun.
Claire brought out three dresses for me to look at. The first was an emerald green spaghetti strap with a tight bodice that flared into an A-line that capped at knee length. The second was a strapless floor-length coral gown that had an iridescent shine to it. But it was the third that caught my attention.
The object of my desire was an off the shoulder, navy blue dress with inset sequins and a mid to low-thigh hem. The bodice was fairly form fitting but the skirt was wavy and puffed out from layers of tulle underneath the main fabric. It was so feminine and pretty that I reached out and touched the fabric with my hand.
"I take it you like this one?" Claire asked.
"I do!" I replied excitedly. "I like them all, but that blue one is simply gorgeous."
Claire nodded her approval. "Why don't you take all three to the fitting room and try them on? When you're ready, I'll help you with the fitting."
I couldn't wait. I bounded into the changing area with a hop in my step, ready to play dress up. Why hadn't I ever thought to do this before?
Of course, it would be a little awkward if I kept coming in to try on dresses but never purchased anything.
I tried on all the items Claire brought for me. The coral dress was pretty, but it was too formal for Homecoming and a little out of my price range. The emerald dress looked amazing with my skintone and I loved it until I slid the navy blue dress up my body. It felt and looked amazing. Claire even brought me some jewelry and a pair of 3-inch heeled, open-toe sandals to wear with it.
This was definitely the dress for me, but Claire noticed a slight frown on my face.
"What's wrong hun? It looks great on you." She asked.
"It does, and I absolutely love it...but I wish I filled it out in the chest a little bit more, if you know what I mean."
Claire smiled and gave a knowing nod. "I think I may have just the thing for you. Wait right here."
She disappeared to the back of the store while I admired my reflections in the mirrors. I could probably pull off A-cups with the addition of a bra, and I still loved how I looked, but a more feminine figure definitely wouldn't hurt.
Claire returned with what looked like a strapless bra.
"This should be your size." She said as she handed it to me. "It won't give you bountiful breasts, but it will help push up what you have and give you some cleavage."
Claire motioned to her own chest with cupped hands and smirked.
I slid the dress down and put on the strapless bra.
"It's really tight!" I exclaimed.
"It needs to be," she responded. "It needs to force everything into place."
That it did. I couldn't believe how this little thing squished all of me up into a fair amount of cleavage. I pulled the dress back on and marveled at the wonders of a pair of boobs.
"Wow!" was all I could manage.
"If you think that looks good, try a little bit of bronzer on the sternum and highlights on the top of your breasts. It will make them appear even bigger."
I just smiled at the mirror, happy as could be.
"Tell you what, if you buy that dress, I'll throw in the push-up bra for free."
"Claire, I think you have yourself a deal."
I bought the dress, a handbag, a silver necklace, and matching clip-on earrings. I didn't get the shoes because I wanted a closed-toe and all she had were sandals. A quick trip to the mall fixed that though, as I found a 4-inch heel, silver pump with an almond toe, and they had it in my size 9.
As I was leaving the mall, I glanced in Victoria's Secret and saw the most amazing lingerie set on display. It was a matching blue with shiny silver accent jewels and silver straps. It came with a bra, thong, garter belt, and nude, almost white looking glossy stockings with a navy lace top. The bra was even able to be worn strapless or as a halter. I was transfixed.
I went in to peek at the price tag.
"$149.99!" I gasped. That's as much as I paid for the rest of my wardrobe for the dance. I imagined what it would feel like to slide the silky smooth garments on and how they would look as I got ready for the dance. Unfortunately, I couldn't bring myself to spend that much money on something that wouldn't be seen anyway. It would have to remain just a fantasy.
I brought my items home and stashed them away in my closet, where my parents wouldn't bother looking. I was still unsure about where I would be getting ready for the dance, but I already had butterflies thinking about putting on all the finishing touches. Of course my mind kept drifting back to the lingerie I couldn't afford.
I texted Jason and described my outfit. He seemed excited and I almost sent him a picture, but decided that the first time he saw it should be in person. He told me that his parents were going out on the day of the dance and that I could use his house to get ready. I was to be there around 5 o'clock and park down the street so no one saw my car later in the evening.
It was the day before the dance and everything seemed ready to go. I had a nervous excitement about me and I couldn't wait to get home from school and get all of my things together. The only problem was that I couldn't get that lingerie set out of my head. I decided that after class, I'd drive back out to look at it, hoping it wouldn't be as grand as I was making it in my head.
The day dragged on forever, and when the bell finally rang, I sprinted to my car and sped back to the mall. I was huffing and puffing by the time I speed walked up to Victoria's Secret. There it was. Staring back at me. It felt like there was an angelic glow around the display.
I thought to myself, "Of course it would look better in person than I had been picturing it all week."
Just then, a saleswoman broke me out of my trance. "Can I help you with something?" She asked.
I felt like I was possessed. "Yes, I'd like to buy this set." I said robotically.
I was cursing myself as she bagged the items for me, but when it came time to pay, I dutifully handed her my credit card.
"Fuck, I need to make sure my mom doesn't see this bill." I thought to myself.
The saleswoman cashed me out and commented, "Thanks for shopping...whoever that is for is quite the lucky lady."
"You have no idea." I said with a grin.
I couldn't believe that I spent that much money on lingerie, but my heart felt full. I couldn't wait to put it on. Fortunately, I only had to wait a day.
After so much anticipation, the day had finally come. I spent the entire day trying to stop myself from clock watching. I still couldn't believe that I was actually going on a date with my best friend, let alone going to a school dance as a girl. I packed all of my things in an overnight bag, and said goodbye to my parents as I headed over to Jason's house. Thankfully, they were none the wiser to my real intentions.
I arrived and parked down the street as Jason requested. Like he said, his parents were already gone for the evening. He let me in and after a minute or so of awkwardness, he told me I could use his parent's bedroom to get ready.
I dropped my bag on the bed and just sat down for a minute. I felt like I had to catch my breath. Was I really doing this? Jason was down in his room getting ready, and I was about to transform myself into a woman for him in his parent's own room? What was I thinking? I was starting to hyperventilate.
I tried to calm myself and set upon my task of getting ready, but nothing could stop my heart from thundering inside my chest. Finally, I looked at my bag with a frown and realized that inside waited an immaculate dress and matching lingerie. My breathing finally slowed and I was able to focus on what I needed to do.
Having already shaved, waxed, and washed my whole body, I jumped right into finally putting on my outfit for the evening, starting with my lingerie. I slid the sheer nylon stockings up my smooth legs, releasing the lace top at the highest point of my thighs with a snap. I pulled up the thong and tucked my meager penis away, making sure to present a smooth front. I then fastened the garter belt on my waist, above my hips. The straps and accents cascaded down my abdomen, coming to a rest just above the top of my panties. Lastly, I leaned over and clasped the silver garters to the blue lace of the stockings.
Fortunately, the Victoria's Secret bra was a bit bigger than the push-up I got from the dress store. I layered the blue lace bra on top of the nude pushup and admired the sudden appearance of full B-cup breasts and a fair amount of cleavage. I took Claire's advice and added the makeup to make the cleavage more pronounced. She definitely knew what she was talking about. I couldn't believe how round and full my chest appeared.
I finally slid into the dress, pulled it up onto my shoulders, and struggled to contort myself in a way that would allow me to get at the rear zipper. The bodice dripped like a liquid off my chest and then flowed outwardly at the waist, ending in the sparkly tulle a few inches above my knees. I posed in the mirror and admired my new breasts and ample rear, still showing despite the puffed skirt.
Now it was time to transform my face. I set up in the bathroom and went to work on my makeup. I applied foundation, concealer, contouring, highlights, and a pink lipstick that made my lips plump up. I pulled out all the stops and used all the tips and tricks I had learned from watching countless makeup tutorials. I applied feathery false lashes and gave myself a smokey eye shadow that started dark near the eye and then transitioned to blue and silver in the corners.
I styled my hair with a lazy wavy curl. It rested nicely just above my shoulders and cut my face in a way that seemed to thin it out. Finally, I put on my dangling, silver earrings, matching necklace, a bracelet, and metallic blue press-on nails. I then slid my feet into my 4-inch pumps and gave myself a twirl to admire in the mirror.
The woman looking back at me was drop-dead gorgeous. I knew I was good, but the sight before me was a work of art. I was so happy, I could hardly contain myself. I finished off with a few sprays of perfume on my neck and breasts, grabbed my clutch, and then headed out of the room to find Jason.
The upstairs was dead quiet, so I quietly crept downstairs to find him. My heart was pounding, and I found myself gripping the railing extra tight as I discovered a weakness in my knees from the anticipation of Jason seeing me for the first time. The door to his room was open and I caught a glimpse of him with his back to me, affixing his tie. I stood in the doorway and waited for him to turn and finally see his date for the evening.
Jason turned and saw me leaning against the door jam, a small smirk on my face, confident in my look and trying like hell to hide my nerves.
His eyes shot open and his jaw hung low. I took that as a good sign.
"Well, how do I look?" I asked, trying to elicit a reaction.
"You look...incredible! I can't believe it. I mean, damn! You'll be the hottest girl at the dance."
"Now I know you're lying." I said.
"Seriously Allen...actually, what should I call you?"
"Oh, I hadn't thought about that. Call me Allison." I responded.
He pondered for a second and then said, "Seriously ALLISON, I had no doubt you'd look good, but I did not expect this. You look, mature, and sexy, and just wow! I don't know what else to say."
"Well thank you," I said, embarrassed by all the compliments. "You look pretty dapper yourself, Jason."
And he did. He wore a light gray suit with a navy blue button-up shirt to match his date. I was actually really impressed. Jason cleaned up well.
"Oh, I almost forgot," Jason exclaimed. "I got you these."
Jason turned and grabbed a corsage from the bed.
"May I?" He asked.
"You may." I nodded. "But I totally forgot to get you one." I confessed.
"No worries, having you on my arm will be all I can probably handle." He joked.
Jason pinned the flowers to my dress and I thanked him with a small kiss on the cheek. He blushed in embarrassment and wiped the lipstick from his cheek.
"Shall we?" He asked.
I placed my arm in his and he led me to the stairs, allowing me to go up first. As we got to the top, I was startled to see Jason's mom in the living room.
"Mom, I thought you left?" Jason said in a panic.
"I did, but of course your father forgot the tickets. We're on our way now...Oh, is this your date?"
Jason crumpled under the pressure so I jumped in.
"Hi Mrs. Trevino, I'm Allison. It's nice to meet you."
"Well aren't you lovely?" She said, but then she paused and gave me a curious look. "You look awfully familiar. Have we met before?"
Jason's eyes bulged out of his skull at the question from his mother.
"No ma'am," I responded calmly. "I don't think we have."
She let it go. "Hmm, okay. Well you kids have fun tonight. Be safe."
Jason's mother left and I had to steady Jason on his feet with a hand on his back and another holding his arm.
"You okay there, big guy?"
"I thought she knew it was you, Al. I panicked. Sorry."
"It's alright," I said. "But yeah, my heart leaped into my throat there for a second."
Jason drove us to the dance and we arrived a little after 7 o'clock, so as not to be the first one's there. I grew in confidence that none of Jason's other friends would recognize me after the run-in with his mom. He parked and escorted me to the dance as I rested my hand in the crook of his arm. Jason is 6'1", and in my heels I came up a little bit higher than normal on him, but he was still half a head taller and had much longer strides, which he had to subdue in order to allow me to keep up, click-clacking in my silver pumps.
We settled in at the dance and Jason showed me off and introduced me as Allison to a few of his guy friends. They were much more receptive than at the party two weeks ago. We danced to a few songs and then gathered around the snacks and drinks for a bit.
"I'll Make Love to You," by Boyz II Men came on, and most of the couples headed off to the dance floor. Jason extended his hand to me and asked to dance, which I happily accepted and allowed him to lead me to the floor for a slow dance.
Jason put both of his hands on my lower back and I wrapped mine around his neck, pulling him close. It was awkward to be doing this with him, but at the same time felt right. Our bodies rubbed together as we swayed to the song. Before long, I felt something hard pressing into my pelvic bone. Jason had a hard-on. For me! I just grinned from ear to ear as I leaned into it and enjoyed the rest of the dance, trying to keep him as turned on as possible.
As the dance ended, the same girl that thought I was her girlfriend at the party approached us.
"Damn Jason, do all your friends from your old school have nice asses?"
He chuckled a nervous laugh, but I turned and addressed the girl.
"Um, thanks...I think. I'm Allison."
"I'm Katy." She responded. "A few weeks ago, Jason brought a friend to a party. I accidentally thought he was a girl because he had such a plump ass...so sorry about that."
"It's alright," I said. "I'm proud of my behind." I slapped my butt for effect.
"Are you two coming to the party at Dan's tonight?"
"Yeah, we'll be there." Jason replied.
"Great, Allison, why don't you come with me. I'll introduce you to a few of the girls."
Katy grabbed my hand and led me away from Jason. I turned and gave him a little wave of the fingers as he left to join a group of guys.
"You look incredible, by the way. I love your dress!" Katy complimented me.
"Thanks. Yours is very pretty too."
She wore a red spaghetti strap minidress that seemed to show off miles of bare thigh. I had to remind myself that I was Allison and not Allen. In fact, it seemed that all the girls at this school were insanely attractive. Maybe it was just being in a new environment with unfamiliar faces, but I needed to refocus on and actually become Allison instead of pretending to be Allison.
Katy introduced me to some of her other girlfriends. They were all very nice, welcomed me in, and complimented me on my outfit. They also complimented me on my date. It seemed that most of them found Jason very attractive and couldn't figure out why he was always fretting over the girls at his old school instead of dating one of them.
A girl named Jennifer commented, "Now I know why Jason has been so hard to get...he's got girls like Allison squirreled away from his old school."
"Interesting," I said. "He told me that he had a date from Sandberg and that she bailed on him. I was his fallback."
"Lies!" They all yelled. "If he had a date from here we would have known."
"Fair enough," I laughed. "I guess he was just working up the courage to ask me."
I was happy that the girls accepted me. It made the rest of the dance enjoyable and I was glad that I could both have fun with Jason and enjoy a friendly group. The guys rejoined us and pulled the whole mass of us onto the dance floor. I danced with Jason, Katy, and a few of the other girls.
While dancing with Katy, I overheard one of the other guys asking Jason if we were dating. I let him squirm under the pressure before I butted in and pulled him away with a big kiss on the cheek.
"Are these guys trying to steal me away from you babe?" I asked him playfully.
He gave a nervous laugh. "It seems Johnno here had an eye on you."
I frowned his way. "Sorry hun, I'm all his." I said as I thumbed at Jason. I wrapped my arms around his neck and pulled him into an embrace as we danced.
"You weren't trying to sell me off to the highest bidder, were you?"
Jason finally relaxed. "Never, but it seems you've caught the eye of a few of the guys here. You better be careful."
I pulled back and smiled at him. "I'm having fun. I can handle myself. No show your date a proper dance."
He pulled me close as we slow-danced. I rested my head on his shoulder, and before long, I felt that familiar pressure against my pelvic bone. I don't know why, but I loved that I had the ability to turn him on that way. I should have been appalled, but I enjoyed feeling his manhood rub against me as we rocked back and forth.
The time seemed to fly, and before I even realized the dance had wound down, people started leaving for the after party. Katy came up to us as we were enjoying one final dance.
"We're all gonna head back to Dan's, hope to see you there Allison." She said as she tapped me on the shoulder.
"We'll be there soon. I want to finish this dance with this fella here first."
"You two are so cute," she commented as she turned and galloped back to the group.
I pulled Jason close and enjoyed the final dance of the evening.
"Thanks for bringing me here, I really had a great time. I hope you did too." I whispered to Jason.
"I did. Thanks for being a great date Allison."
I don't know what happened, but something came over me upon hearing Jason say those words. I reached up with a hand to grab his head, I pulled him toward me and pressed my lips against his, holding him in a kiss for a few seconds before finally releasing him.
Jason stood there stunned.
"I'm sorry," I said panicking. "I...I don't know what came over me. I just got carried away."
"It's alright," Jason said. "I just didn't expect it. It...it was nice."
I felt like an idiot. We left the dance and made our way to the party, but I couldn't shake the queasiness in my stomach. I needed a drink or several to calm my nerves. Jason reassured me that the kiss was accepted, but I was still shaming myself in my head. After tonight, I go back to Allen. I shouldn't have kissed my best friend.
Fortunately, Katy had a drink ready for me when we arrived. I was starting to think she had the hots for me too, but was mostly relieved to get a few minutes away from Jason and get some liquid courage inside me.
Katy nudged me. "I saw that kiss. That was something."
I grimaced. "Oh shit, you saw that?" I asked.
She whispered in my ear. "Don't tell anyone, but the basement is open. The stairs are in the back, around the corner from the bathroom. There's a couch and some chairs down there if you and Jason want to sneak off and finish where you left off."
I just stared at her wide eyed, unsure of why she offered this information.
"If you're wondering why I know, Dan may have taken me down there to show me around during his last party." She said as she made air quotes around "show me around."
I thanked her for the information, gulped a drink, and grabbed another before I made my way back to Jason. We chatted and I drank. A few people wandered off to play drinking games. The party was fun, but I preferred the atmosphere of the dance. It felt more intimate.
Jason and I went to watch a few rounds of beer pong. It was actually pretty funny watching Katy beat up on Dan. The guys definitely gave him a hard time for losing. After a few drinks, I asked Jason to walk me to the bathroom. He was a gentleman and showed me the way, even though I had been to a party at the same house just weeks ago.
"Can you wait out here for me please?" I asked before I went in.
I went in and did my business. A quick reapply of some makeup and a once over in the mirror and I was ready. I couldn't believe I was even thinking of doing this, but I wanted to capture a little more of that spark that I felt when I kissed Jason at the dance. I opened the door and thought to myself, "Here goes nothing."
I left the bathroom, grabbed Jason by the wrist, and glanced in the direction of the party to make sure no one was watching as I pulled him around the corner.
"What are you doing?" He asked, confused by my rushed movements.
"Come with me," I whispered as I led him to the basement.
It was dark, but I found a small lamp on an end table and turned it on. I led Jason to the couch and sat next to him.
"What's going on Al?" Jason asked, his voice quivering.
At least he was as nervous as I was.
"I wanted to get you alone for a minute. Katy told me about the basement and said it was okay to bring you down here." I hoped the confidence I tried to display masked my fears.
"Ok Al, what is it you wanted?" He asked, knowing the answer but afraid to hear it.
I grabbed both of his hands and looked him in the eyes.
"I want to kiss you again."
I said it. Out loud. Oh hell, what was he thinking.
Jason broke my gaze. "I...I'm not sure we should." He confessed.
"Just once," I pleaded. "If you don't like it, or you're still uncomfortable, we'll go back upstairs and never speak of it again."
Jason took a deep breath and let it all out in a rush. He closed his eyes and nodded. "Okay."
His eyes were still closed as he sat there and waited for me to make the first move. I leaned over him and pressed my lips to his. They were soft and moist. I inhaled his scent as I kept my mouth against his. I let out my breath with a soft moan as I melted into his arms.
Jason wrapped me with his arms and parted his lips, ever so slightly. I took advantage and slid my top lip in the opening, allowing me to suck his bottom lip into my mouth. He tasted heavenly. I chewed his bottom lip for several moments, eyes closed, practically floating on air as I made out with my best friend.
Our lips smacked as I briefly pulled away. We both opened our eyes at the same time. I smiled at Jason and he returned it with one of his own. That was all the cue I needed.
I swung my right leg over him and straddled his lap. On my knees, I hovered just above his face. I took his hands and placed them on my stocking covered thighs, guiding him up and under my skirt. Then I grabbed his face with both hands, brought my mouth back down to his, and plunged my tongue into his mouth.
We practically devoured one another. The tension and sexual frustration of the night, released in one big explosion of hands, lips, and tongues. I ground my panty covered crotch into his and in no time at all was rewarded with a stiffness pressing back into me. I giggled into Jason's mouth with a grin as I felt his hard cock press into me.
I pulled away from his hungry mouth, leaving him wanting more. I looked to his crotch and ran my hands down his chest, along his shirt, toward his belt and fly.
"Um...Al. Allison, what...what are you doing?" He mumbled.
I just put a finger to his mouth and said "Shhhhh. Let me do the work."
Just then, the lights blazed and footsteps trampled down the stairs. I quickly rolled off Jason, adjusted my dress, and was greeted with a chorus of hoots and howls.
"Uh oh, busted." I heard Dan's voice from behind the sofa. "What were you two kids doing?"
Jason panicked again. "Uh, nothing. We were just talking."
I stood and stared at Dan, hand on my hip and head cooked, showing my displeasure.
"Well, if you really want to know, we were making out, Dan! Thanks for interrupting."
The crowd "Oohed" and laughed at Dan as I pointed out the obvious.
The party moved to the basement and I grabbed myself another drink, bummed that my escapade with Jason was cut short.
"Sorry about that," Katy confessed. "I told him to leave you guys alone. He got suspicious when you disappeared for a bit and I told him I sent you down here. It's my fault, I shouldn't have told him."
"Katy, no. Don't worry about it at all. I got what I needed. Thank you." I appeased her conscience with a hand on her shoulder.
"Are you sure?" She still questioned.
"Yup, I'm sure. In fact, I'm gonna see if Jason wants to get outta here. It was really nice meeting you."
Katy gave me a devilish grin. "Have fun. He looks yummy. It was nice meeting you too. Have Jason bring you to the next party. I'd love to see you again."
"I will," I said with a wink of the eye.
I approached Jason in the back of the room.
"Let's get outta here."
"And go where? We're supposed to stay the night here." He confusedly asked.
"Let's go back to your place. Your parents should be home and in bed by now" I said.
"And tell them what in the morning?"
I thought quickly on my feet. "When we get up in the morning, you tell them that there was a lack of sleeping space, so you went home. You tell them I took a girl to the dance as well and didn't want to drive home after the party. I'll clean up and be Allen again before your parents suspect anything."
Jason thought about it for a few seconds, but I could tell I had him hooked.
"Okay," he finally gave in. "Let's go."
As I followed him up the stairs I looked back and caught a glimpse of Katy watching us leave. She gave a wink and a kiss. I returned her devilish grin from earlier and gave her a subtle wave as we disappeared up the stairs.
By time we got back to Jason's house, it was approaching 2 o'clock in the morning. The house was dark, and we quietly snuck in and made our way downstairs to his room. I was a bit tipsy and the sound of my heels going down the stairs made me giggle, but Jason was sober and had to quiet me several times before we got to his room.
We went inside. Jason locked the door while I turned on his bedside light. We turned toward one another and both briefly paused to look each other up and down. The moment over, our bodies clashed together like the meeting of the tides. His mouth found mine this time. He rewarded my persistence with his tongue digging deep inside my mouth.
I untucked his shirt and started undoing his buttons from the bottom up. It took me forever as I fumbled with each due to my long press-on nails, but once I got unencumbered access to his chiseled chest, I ran those nails over his pecs and down to his waistband. He shivered from the feeling of my nails against his bare skin.
I let Jason envelop me with his presence. He pulled me in close, my breasts pressed up against his bare chest. That familiar feeling of hardness pressing into my pelvic bone returned and gave me a sense of warmth and desire I had never felt before.
Gone were the thoughts of Allen and what tomorrow brought. All there is is Allison and Jason and this moment. I brought my lips to his chest and kissed him there before slowly tracing my lips down his abs to his waist. I looked back up into Jason's eyes and saw pure desire. I smiled at him briefly and then returned my attention to his belt, unfastened it, unzipped his fly, and let his pants fall to his ankles.
Jason stook there in his boxer briefs. The tip of his rock hard cock just barely peeking from the top of his waistband. It finally occurred to me that he was big. Much bigger than me. Probably at least 8-inches. I ran a finger along the front of his briefs, teasing his cock with my long nails, eliciting another shiver. I kissed the outline up and down with my plump, pink lips. Finally, I flicked my tongue at the purple head that continued to grow from the depths of his groin.
I grabbed the waistband with both hands and pulled down, setting Jason's manhood free from its enclosure. It stood there in front of me, like a mighty redwood from the deep forests of Northern California. I grabbed it mid-shaft with my right hand as I caressed his glans with my thumb. I then took one of his huge testicles into my mouth, holding it there with some pressure before finally letting it fly free with a "pop."
I licked the length of his shaft, coating it with the juices and saliva from my tongue so that it glistened in the soft light from the lamp. I slowly began to stroke Jason's cock with my right hand as I worked the left side with my tongue. Jason moaned as his head rocked back in pleasure.
"Oh my God," he whispered.
"I know," was my response.
I rose up on my knees as Jason still towered over me. I brought my lips to the tip of his penis and kissed the head. Then I parted them and let the fullness of Jason's cock penetrate my mouth. It was slightly salty with a musky aroma, but what caught me off guard was how hard and hot it was. It burned with a desire that could only be quenched by my mouth, and I gave it the reprieve it craved.
I bobbed up and down, taking as much of the length as I could before coming back off the top with an audible "smack" at the end of every cycle. I had obviously played with my own dick before, but I still couldn't believe how hard Jason was. He felt as hard as a rock and the heat from his dick warmed my mouth as it flooded with saliva.
Jason widened his stance as I got into a rhythm. I continued to stroke his dick and fondle his heavy balls as I worked the head with my mouth. Jason grabbed my hair with both hands and pulled, guiding my mouth up and down his cock at a medium pace. I squealed with pleasure at the feel of his hands forcing me up and down his dick.
I was in heaven and it was obvious that Jason had finally relaxed and was letting this happen. The tension between us all night was palpable. Now, all that worrying about norms and secrets was building up in his balls, waiting to explode into the waiting depths of my mouth.
I worked his cock with a fever I had never felt. I wanted to make Jason cum. I wanted to pleasure him more than any girl at that stupid party ever could have. I wanted to taste that sweet, sticky cum on my lips and let it run down my throat.
Jason's legs stiffened as he locked his knees. His weighty testicles rose in preparation of releasing a torrent of hot, sticky fluid into my wanting mouth. I worked his long shift with my hand as I locked my lips around Jason's cock head and waited for my reward.
At last, it came with a large grunt from Jason. His knees buckled as he unleashed spurt after spurt into my hungry hole. I sucked down gulp after gulp, but Jason was still cumming. I counted six streams of cum as I hurriedly did my best to swallow every delicious drop he provided.
I could take no more and thankfully neither could Jason. He fell back onto the bed, pulling his clock from my mouth just as I had captured the last of his cum. I let it sit on my tongue as I savored the taste and texture, making a show of it as I let it drip down my glossy pink lips before slurping it back into my mouth and swallowing it down.
My breasts heaved up and down in my dress as I finally caught my breath.
"Holy shit," exclaimed Jason. "That was...amazing. How'd you learn to do that?"
I wiped the remnants of cum and spittle from the corner of my lip with my fingernail before sucking it clean and giving Jason a devious smile.
"It was my first time." I said with an innocent smile and a shrug of my bare shoulders.
"Well...it was, I mean you were incredible. I've never gotten lightheaded from cumming before." Jason complimented my dick sucking prowess.
"I'm glad that I have the Jason "Seal of Approval," and the paperwork to go along with it." I quipped as I attempted to clean off any remaining cum from my lips.
I got up off my knees and kicked off my heels before straddling his prone body on the bed, placing my white hot crotch against his still hard and throbbing cock.
"Wanna know the best part?" I asked.
"What's that?" Jason said, finally catching his breath.
"You can fuck me and not have to worry about getting your Homecoming date pregnant." I said with a little giggle, bringing my hand to my mouth for effect.
Jason's eyes shot open. "Um, a blowjob was one thing Al. I don't know if I'm quite ready to have sex with you. This is all pretty new territory for me."
"Wow," I laughed in earnest. "All that blood leaves your head and you forget how to take a joke." I said, pushing his shoulder as I rolled off him to the side to lay next to him.
"Don't forget. This is all new to me too. I'm kinda dealing with these feelings as they appear." I admitted.
"Oh...Okay, that's true. Sorry Al."
"Nothing to be sorry about," I said. "I just had an amazing night with my best friend."
Although I played it off well, I was a little disappointed. Only God knows why, but my first day as a woman and I was ready to lose my virginity to my best friend of over a decade. For the first time since this saga started, however, I finally felt comfortable in my own skin. I no longer felt like I was playing a role in a play. I wanted to be Allison and I wanted to be with Jason. I had no idea how he felt, but that was a conversation for another day.
We chatted and laughed about the evening as we laid side by side on the bed. I ribbed Jason for the terrified look on his face when Dan caught us making out.
"I thought you were gonna have a stroke." I laughed out loud.
"Shhh, you'll wake my parents." He scolded. "But yeah, I almost shit myself."
It took me a minute or two to regain my composure, tears beginning to form in the corners of my eyes from laughing. I sat up and pulled myself up off the bed. Jason pulled up his boxer briefs and watched me with a careful eye.
I spun my back to him and presented my behind, looking over my shoulder back at Jason. He continued to stare at me with wide eyes, dumbfounded by the vision before him.
I coughed to break his gaze. "Um, care to help me with an unzip?"
"Uh, what?" He said lazily.
"Well, I'm not wearing this dress to bed...and I had a hell of a time getting it zipped up on my own. I don't really feel like contorting myself in my current condition." I lectured.
"Oh. Yeah, okay. No problem."
Jason slipped off his pants from around his ankles and stood to help me with my dress. He reached out and grabbed the zipper at the nape of my back like it was made of hot coals, afraid that he might get hurt if he touched it too long. He unzipped me with a long, slow pull down to my lower back, revealing the back of my bra and the top of my garter belt.
I turned to face him and was delighted to see him wide-eyed and nearly stupefied, mouth slightly agape. I slid one arm from the dress and held it to my chest as I removed the other. Jason didn't move an inch and his gaze never left my body. I moved my arm away from my body and let the dress fall to the floor, creating a pile of polyester and tulle around my stocking clad feet.
I stood before Jason in my secret weapon. The outrageously expensive lingerie that I just had to have to make me feel sexy. I was now glad that I had splurged on the purchase. Jason drank in the sight of me in my lingerie. A muse, basking in the soft glow of the lamplight. I stepped out of the dress with deliberately pointed toes and gave myself a good once over, enjoying the torment I was giving this poor boy.
Never before had I felt power over another person like this. I knew, no matter what I did, I had Jason's complete and undivided attention.
I motioned toward the bed and grabbed his hand as I tiptoed toward it.
"Well, shall we get in bed? I'm getting sleepy." I yawned.
"Um, you're gonna sleep in...in that." He stuttered, motioning to my outfit.
"Well, it's this or nothing at all," I said. "I'll clean up in the morning. You gonna join me or just stand there and stare at me?"
"We're going to sleep in the same bed?" He asked as if ashamed.
"Yeah, I'm not sleeping on the floor tonight. I think I've earned that." I said as I gazed at the wet spot on his boxers. "You're welcome to sleep with me in the bed or sleep on the floor yourself, but having slept on your floor, I recommend joining me in bed."
I was enjoying this newfound power and confidence. It emanated from me like a guiding beacon. I knew Jason wouldn't be able to resist, and as if I commanded it, he joined me in the bed as I pulled back the cover and patted his side of the full-sized mattress.
"Don't worry, I won't bite." I teased.
Jason removed the remainder of his clothes with the exception of his boxer briefs. I couldn't say that I was disappointed in his bedtime attire, much as I was confident he was enjoying mine, even if he was doing his best to hide it.
He finally joined me under the covers. I gave him a hug, making sure to press my breasts up against his chest, and a small peck on the cheek to thank him for a wonderful evening. We laid down and covered up. My pinky played with his hand and I teased his leg for a few minutes with my still stocking clad foot before finally rolling over and curling up into the little spoon position.
I thought to myself, "That ought to give him something to think about tonight."
I fully did not expect him to roll over and join me as the big spoon, but for once Jason finally surprised me. After several minutes of laying on his back, he rolled to his side and placed a hand on the lace top of my stocking. I reached up with my right hand and intertwined our fingers, making sure his hand didn't leave my thigh.
Despite his new confidence, I could tell he was still apprehensive. Jason didn't move his body any closer to mine, despite having his hand firmly caressing my thigh. I decided to take matters into my own hands and backed my plump butt back into him, forcing Jason to embrace all of me. My devilish grin returned as he moved his hand to caress my hip and ran it along my entire side.
I could feel that tell-tale pressure between his legs returning, this time pressed firmly against my backside. I loved what I could do to him. I moved myself back and forth, up and down, eliciting a small moan from Jason.
"Do you want me to stop," I whispered.
I was giving him the option, but I already knew the answer.
"No, don't stop," he said under his breath.
I continued to grind my butt into his hardening cock until it reached its apex, head once again peeking out from the waistband. I licked my hand and reached behind me to grab his dick. I stroked it, lubing it up with several mouthfuls of spit and saliva.
Once I had it to my liking, I pulled my thong to the side and pressed the head of his beautiful cock to my opening.
"Slide it in," I whispered, giving him the go-ahead to deflower my ass.
Jason didn't say a word, but I received his response through a firm grip on my hips and an increased pressure against my hole. I moaned as the pressure built, my virgin ass clinging to its last bit of decency before it finally gave way and opened to allow the intruder inside. The head slid inside of me, giving me a new sense of pleasure and pain. I gasped and sucked in a large gulp of air.
"Are you okay?" Jason asked, afraid that he had hurt me.
"I'm fine," I grunted. "Just not used to it. Stay right there for a minute."
Jason stayed completely still. I caught my breath and my ass began to welcome this new feeling of immense pressure. My sphincter finally relaxed and I felt the tension leave me from my back through my toes. I curled my toes in anticipation of the next sensation.
"Okay," I whispered. "I'm ready."
Jason delicately increased the pressure as he leaned into me. His beautiful cock disappeared into my ass inch by inch. I only wished I could have seen the sight.
"Oh my God," I purred as Jason filled me from behind. "That feels so good."
"You feel amazing too," Jason moaned.
He pulled back and re-entered in short, shallow thrusts, allowing me to enjoy and relish the fullness his dick offered.
I reached my free arm back to touch Jason's face behind me.
"You're filling me up. Your dick feels amazing. Please don't stop." I begged.
Jason took that as cue to pick up the pace and increase the depth of his strokes. My ass welcomed the challenge and I began to meet his thrusts with one's of my own. You could begin to hear the muffled sounds of his thighs bouncing off of my behind under the covers. My moans and cries of pleasure became more pronounced, urging a proper fucking.
Jason finally became emboldened by my persistent mewing and flung the covers off of us. He grabbed my right thigh and pulled, rolling me on top of him as he rolled with me. I spread my legs and finally felt the full depth of his cock as he cupped my breasts from behind and pulled my back into his chest.
He pawed at my chest, gripping my breasts tightly atop my bra as I arched my back into him. With my new leverage I was able to plant my feet into the bed and lift myself up and down on his rigid cock. I was finally able to fuck him back, and fuck him back I did. I was a woman possessed. I bucked up and down with my hips, riding his amazing dick like a bucking bronco.
Our breaths built to a crescendo. Sweat started to pour down my face. My ass cheeks slid against his hips. Jason had finally freed my meager breasts from their enclosure and had a firm grip on each with his strong hands. I continued to ride him like my life depended on it, making entirely too much noise in the process.
Still wearing the stockings and thrashing on Jason's dick like a mad woman, my feet slipped out from under me and I bottomed out on his cock, taking it to the hilt, deeper than any previous thrust. Jason moaned and spasmed beneath me. My legs locked out straight as I rode his orgasm to completion.
"Ugh, ugh, ugh," he grunted as he emptied his balls into my ass.
Jason gripped my hips and held himself as deep as he could reach until he shivered from completely draining his seed into me. I collapsed onto his chest and Jason lightly ran his fingers from my thighs across my hip bone and up my stomach. I got goosebumps from his touch.
He laughed at my sensitivity. I grabbed his arms and wrapped them around me, taking in his warmth as he embraced me from behind.
"Ho...ly...shit," he gasped through labored breaths. "I have no words."
"No words necessary," I purred back at him, enjoying the feeling of his embrace as his cock softened and began to slide from its place inside me, leaving a slimy trail of spit and semen in its wake.
Once Jason's dick finally slid free from my ass, I rolled off from on top of him and cuddled into his left arm, draping my left arm across his midsection and my left leg across his. I fondled his chest with my fingernails, lazily drawing circles on his skin. He turned his face toward me and I showed no hesitation in taking his bottom lip between mine, savoring the salty flavor of our combined sweat. Slowly, we drifted off to sleep in that position.
I woke after only a few hours of sleep as the sun began to peek through the bedroom window. I quietly snuck out of the bed and made my way to Jason's shower. I scrubbed off every last bit of Allison, including all of the makeup, perfume, and bits of dried semen, and once again became Allen. I dried and dressed in my street clothes and crept back into the bedroom.
Jason was still asleep, and I decided that it was probably best to be gone before he woke. A conversation needed to be had, but I had a feeling it would go differently than I hoped if I had it dressed as Allen. I made my way upstairs and headed for the door, when Mrs. Trevino called out from the kitchen.
"Allen, I didn't know you were here."
"Oh, hi Mrs. Trevino," I said. "I ended up taking another girlfriend of Jason's to the dance. After the party I felt it was safer to just spend the night here. I need to get home and get ready for work though."
"You made a good call. I'm glad you didn't drive home."
I turned for the door, eager to leave.
"Allen, wait." She stopped me. "Did you know Jason's date last night? She looked really familiar, but I couldn't place her."
My heart caught in my throat. "No, I met her for the first time last night. She seemed nice, I think Jason really likes her."
"She did seem nice, didn't she. Oh well, it will come to me eventually. Good seeing you Allen. Drive home safely."
"Bye Mrs. T."
I turned about face and double timed it down the street to my car before Jason's mom placed how she recognized Allison. I finally made it home and passed out in my own bed. It was an amazing night, but I was drained, emotionally and physically.
Over the next few weeks, I was eager to see Jason again, but I had to pick up extra shifts at work to pay for that lingerie I charged on my credit card. I made sure to switch the billing to e-statements so my parents didn't see the charge and paid it off as soon as I made the money. I was skeptical when I bought it, but given the results of the evening, I think it's safe to say the gamble paid off.
After two weeks of hard work, I finally had a Friday off. I sat down to veg out in front of the TV and just relax. I had finally gotten into a show on Netflix when my cell phone buzzed. I shot a glance at the screen.
"Incoming call from Jason," it shined brightly in the dark room.
I picked it up and answered, "Hello?"
"Hey Al, it's Jason...so um, there's a party next Saturday..."