Learning To Swing Both Ways Ch. 04
INTRODUCTION
This is a time that goes back to the 1970's before the huge threat of aids and an era of condom less sex. Also many people still remained in the closet about their sexual preferences. Aaron Connor was a successful personal financial advisor living in Northern California. He was 28 years of age and had opened his office in Sausalito four years earlier in 1972. The office was a condominium style office with a full bath and kitchen. Aaron furnished it with a pull out sofa but he rarely ever stayed there overnight.
Aaron was a fit young man and he worked out in the fitness center in the next building to his office. He also hiked and rode his bike through the countryside. He was 6'2" and weighed a firm 185 pounds. Aaron had light brown hair that he kept cut short and he had hazel eyes. He was currently dating several girls on the weekends but during the week he got all the action he needed from his administrative assistant of three years.
Cathleen was 35 years old and married but she loved sex with Aaron. She was particularly fond of his 7+" cock. She had short blond hair with a 33-25-35 figure. At 5'5" and 120 lbs. she was small breasted and her best asset was her ass. She was solidly built and exercised regularly and kept herself in excellent shape. Cathleen was not a beautiful girl but she was attractive, dressed very tastefully and was very professional in her appearance and her business behavior. Her sexual behavior was something else entirely.
Their affair started three years ago when Cathleen had only worked there a month. Over the three year period the sex between them was unbelievable. Cathleen loved to suck Aaron's cock and have him cum in her mouth. She also loved the way he filled her pussy and drove her wild causing her to orgasm multiple times. Aaron was thrilled when she offered her ass to him as he loved anal sex and Cathleen's ass was fabulous. They were adventuresome and they never tired of one another.
Cathleen would often douche her pussy and her ass before sex in the office. Aaron would then rim her anus and eat her pussy while she was on all fours. The sofa bed saw a lot of action as all their sex was confined to the office and occurred during the business hours. Aaron loved driving his tongue into her anus and making her squirm with delight. It was wonderful foreplay before he fucked her ass and it never failed to get Cathleen in the mood to be butt fucked.
Cathleen had a desire to be double and triple penetrated but she did not want to introduce another person into there relationship. So they began to include sex toys instead. Aaron would push a butt plug into her ass and then fuck her pussy giving her the sensation of having two cocks in her. Other times Cathleen would suck Aaron's cock with a butt plug in her ass while Aaron fucked her pussy with a dildo. Cathleen went wild with the sensation of her three holes being filled. The sex toys always remained at the office when they were finished.
Having the full bath and kitchen at the condo office was very beneficial. Cathleen would always shower and douche her body before she returned home. She always washed the sex toys thoroughly before hiding them in her desk. The kitchen came in very handy as they always ate lunch in the office and they often had wine with lunch. Sometimes they took baths together and Aaron would rim her asshole while they were in the tub. It was an incredible arrangement for the both of them and they never got bored with each other. In spite of all the sexual activity they got their work done and Aaron had landed some big clients.
Then the day came that they both dreaded. Cathleen told Aaron that her husband was being transferred to the home office in Chicago and they had to be there in a week. Aaron was stunned. In addition to Cathleen being a great administrative assistant, a business day hadn't gone by in the past three years when he didn't have his cock in her mouth, pussy or ass. It would be a major adjustment for them both.
EDNA, CATHLEEN'S REPLACEMENT
Aaron was having lunch with his largest client Mack Harrison when he told him the news about Cathleen. "I know someone that will do a great job for you," Mack offered.
"Really, Cathleen will be difficult to replace," Aaron replied thinking more about the sex than the office skills.
"I've known this person for a few years and Edna hates her current job. Let me set up an interview for you," Mack offered.
"Sure why not, what is there to lose," Aaron agreed.
So the interview was arranged and Aaron met with Edna the following day in his office. Edna was single and had very curly light brown shoulder length hair. Edna was about 5'6", 120 pounds and had a curvy figure with small firm tits and a killer ass. Aaron preferred his women with small breasts, a great ass and flat tummy.
During the interview Aaron sensed that Edna really needed and wanted the job so he decided to test the water. He took a chance and told Edna about Cathleen and how close they had become and how Cathleen took care of his sexual needs. Edna smiled and told him that he would have nothing to worry about. Aaron learned that Edna loved to suck cock and take it in the ass. He couldn't believe his good fortune.
Edna gave notice at the old job and reported to work the following Monday. Aaron wasted no time in testing Edna. He locked the office suite door and then he turned to face his new hire and Edna was already kneeling and reaching for his belt buckle. Edna opened his belt and then unzipped his fly before unbuttoning his suit pants. Edna had obviously done this before many times. Aaron's pants were then lowered to his ankles and then Edna reached for his boxer shorts. Edna hooked her fingers in his boxers and dragged them slowly down his legs. Edna purposely pressed them against his abdomen as they were pulled them down catching his erect cock in the waistband. Edna was successful and as the shorts crossed over Aaron's crotch his cock got hooked in the waistband. Edna stared at Aaron's crotch as the underwear was lowered. When the shorts cleared, his cock sprung out and dangled in front of Edna's face.
"Oh my look at this," Edna said holding Aaron's cock, "You have a beautiful cock and I am going to enjoy this and I am going to make you very happy."
Edna sucked his cock and caressed his balls. Edna was a very accomplished cock sucker and was able to take him deeper than anyone had in the past including Cathleen. Aaron swore he could feel his cock at the back of Edna's throat and Edna seemed to have the ability to massage his cock head with the throat muscles. Edna had Aaron racing toward his ejaculation and he held Edna's curly hair as he began thrust his hips. Edna reached under Aaron's scrotum and lightly touched his perineum which sent him over the edge and he blasted loads of cum in the warm succulent mouth. Edna rapidly swallowed all of Aaron's seed and continued to suck and milk his cock and drain him completely.
Aaron sat back in his office chair and Edna sat across from him. As he recovered slowly from a fantastic blow job Edna leaned back and unbuttoned the blouse. Edna was not wearing a bra so the firm pointed tits stood right out like headlights as the blouse dropped to the side. Edna leaned back against the chair which caused the small tits to stand out even further. Edna definitely had cute tits and Aaron couldn't wait to see that hot ass.
Edna and Aaron talked about the job and he covered more of the details and expectations of the job. Edna was excited about the opportunity and told Aaron that he would never be disappointed. Edna cupped the small firm tits and wiggled them at Aaron as a sign of the willingness to satisfy him. Aaron was already starting to get hard again when Edna stood up and faced away from Aaron. Leaning over the desk, Edna looked back and smiled at Aaron as the skirt was hoisted and displayed a shapely panty covered ass. Edna ass wiggled in an invitation to come and get it. Then Edna slid the panties down but let them rest just below the ass cheeks, it was a very sexy look. Edna took out some lube and greased up and finger fucked the desirable hole with one then two fingers. Aaron's cock was now rock hard and he stood up and moved toward the object of his desire. Edna leaned over the chair and with an arched back which really accentuated the hot shapely ass. Aaron pushed his cock against the nether hole and it slid into the warm passage.
Aaron fucked Edna slowly at first and then he picked up the pace. His thighs were slapping against Edna's buttocks and he held tightly to the shapely hips. Edna used the sphincter muscles to tighten the passage and massaged his cock by clenching and unclenching the muscle. Aaron felt his second load travel from his balls up through his dick as he shot wads of cum deep into Edna's asshole. Aaron leaned over Edna's body and grabbed the firm tits and let the rock hard nipples slip between his fingers. Edna continued to use the sphincter muscle to milk his cock dry of every drop of cum until he finally softened and slipped out.
Edna was fantastic. Aaron had just received a world class blow job and experienced a great ass fuck. He collapsed back in his chair with his pants and underwear still down around his ankles. Edna pulled the panties up and pushed the skirt back down and then sat back in the chair across from him. Edna did leave her blouse undone exposing the cute tits.
Edna smiled and asked, "Was that satisfactory?"
Aaron laughed and replied, "More than just satisfactory!"
"Good I hoped that you liked it and now I have something else to show you," Edna told him hesitantly.
"Well let's see it," he quipped.
Edna stood up again and lifted the skirt up to the waist. Then Edna peeled the panties back down to her knees and revealed a smallish cock. Edna was a guy, a transvestite or transsexual whatever they were called.
"I just had to show you before this went any further but I wanted you to see how I could satisfy you without a pussy first," Edna admitted.
"You certainly had me fooled and you hide it very well," Aaron said somewhat shocked because he had been had.
"Are you angry with me?" Edna asked.
"No not really but I am still in a little bit of shock," he answered.
"Do I still get to keep the job?" Edna asked obviously worried.
"Yes you do," Aaron assured Edna.
Edna and Aaron then shared backgrounds for awhile. He learned that Edna was originally Edward and that he had always been gay. He decided to transition to a female look when he learned more about female impersonators. He had been taking female hormones so his hair grew and he developed breasts. Also he lost his body hair and his skin was very smooth. He was always small in the penis department so it had been easy to hide it most of the time. Even hard he was only about three inches.
Aaron shared with Edna my experiences when he had vacationed in Paris, France. Aaron told Edna how he had first been hoodwinked by a female impersonator in Pigalle. Aaron told Edna that once he got over the initial encounter he was okay fucking them and letting them suck his cock. Between the transsexuals and the French women he had plenty of sex in Paris.
"I have never told anyone about that before today," Aaron confessed.
Edna was pleased to hear about his experiences and that he was comfortable fucking him and letting him suck me cock. They agreed to be discreet and not let anyone else know about Edna's true gender. Edna actually looked very feminine and easily passed for a woman.
"I'm glad that you had some experience with transsexuals as it makes it easier for both of us," Edna answered.
Edna and Aaron confined all of their sex to the office just as he had with Cathleen. On certain days they would lock the office doors and Edna and Aaron would strip naked. Aaron fucked Edna's ass usually twice and Edna sucked Aaron's cock once. Edna would jerk on his cock when Aaron fucked his ass and Edna would shoot three of four times.
One day Aaron was out on a client call when Edna got a phone call from Mack Harrison. "Edna its Mack, how's it going there?"
"Oh hi Mack, everything is great. It couldn't be better. Thanks so much for setting me up with Aaron," Edna bubbled.
"Sure, don't mention it. Do you think that he is ready to meet the ladyboys?"
"Oh definitely, he loves getting blow jobs from me and fucking me in the ass. He will surely love the boys," Edna confirmed.
"Good I'm going to have him over next weekend. Don't wear him out too much," Mack requested.
"Okay, I'll tell him that I have my period," Edna replied and they both laughed.
"Yeah, you do that. Okay I'll be in touch Edna, thanks!"
"Bye Mack and thank you!"
AARON'S SURPRISE OFFER
Aaron met Mack Harrison for lunch the next afternoon and Mr. Harrison was very pleasant as always. They ordered drinks and then their lunch. As they downed the drinks and waited for the food to be served, Mack hit Aaron with a shocking discovery and offer.
"Aaron, I know about you and Edna."
Aaron turned beet red with embarrassment, "Mack I don't know what to say. I'm like the ladies and I have a great sex life but I like fucking Edna too."
"There is nothing wrong with that. I was married once but I like gays too especially pretty boys. I have two housekeepers at my home that are what I call "Ladyboys." They are both petite Thai boys that have nice small tits and curvy asses. They look so much like girls it's scary," Harrison shared with him.
Immediately Aaron wondered what the Thai trannies looked like naked. Aaron felt his cock stir just imagining the two Thai Ladyboys as Mack Harrison called them. He was deep in thought when he realized the Mack was speaking again.
"Aaron would you like to come to the house for dinner this Friday. I will have Mali and Tola prepare an authentic Thai meal," Harrison asked inviting Aaron to dinner.
"That would be wonderful, Mr. Harrison," Aaron accepted.
"Great and then we will have some fun with Mali and Tola after dinner and Aaron, please remember to call me Mack," Harrison replied.
They wrapped up their lunch and left the restaurant. Aaron was already looking forward to the weekend. He had a tentative date with Jill but he would put that off. He also decided to skip sex with Edna on Friday and the best way to handle that was to give Edna the day off.
That Friday evening, Aaron drove to the exclusive suburbs where Mack Harrison lived. As Aaron turned into the gated community called The Meadows he admired the entrance. The guard had Aaron name on the guest list and he gave Aaron directions to the Harrison house. Aaron drove slowly and took in the mansions and estate like homes. One was bigger and more stunning than the next. Then he located Mack's house and pulled in the large circular driveway. Aaron was impressed with the house and thought that some day he might live like this.
Aaron made his way up the walk to the front door and he rang the bell. The delightful chimes echoed through the house and within seconds the front door was opened. Aaron was greeted by a beautiful Thai wearing a jade color silk dress. The dress had a high collar on it and it covered the neck. The Thai's hair was jet black and it was pulled back and tied into a long ponytail. Aaron stared at the Thai in all his beauty before stepping into the foyer. It was had to believe the person was a guy or a ladyboy as Mack said. Then again it was difficult to believe that Edna was a guy.
"Mr. Harrison expecting you, please you follow me," the ladyboy said in a soft voice.
Aaron followed the ladyboy into the main part of the house. He noticed that his jade dress was cut up the side of both legs all the way to the thigh. The dress emphasized his shape as it hugged his small breasts and his perfect round ass. Aaron watched the ladyboy walk in front of him and he focused on the ass as it undulated beneath the tight fitting dress. Aaron felt his loins stir just from looking at him.
Aaron was led into the den where Mack was nursing a scotch. "Hey you found it, great. I see you have met Tola. You will meet my other housekeeper in a few minutes. Tola, please bring Aaron a drink," Mack directed.
Tola made a slight bow and then left the room. When he returned with Aaron's drink the other housekeeper walked in with a tray of snacks. Aaron looked at the other Ladyboy and he looked almost identical to Tola except that his dress was gold.
"Aaron this is Mali," Harrison said introducing her.
"Pleased to meet you both," Aaron said.
The two ladyboys bowed slightly and then left the room. Aaron watched as an ample amount of leg peaked out on the sides of both dresses and their cute round asses rolled with each step. Aaron couldn't believe how beautiful they both were. Mali and Tola looked like two porcelain dolls, they were that fine. Aaron immediately wondered if Mack was fucking both of them. Aaron remembered what Mack had said about being a leg and ass man. Well there were two sets of beautiful legs and fantastic asses on those two ladyboys.
"They have great asses, don't they?" Mack said as if he was reading Aaron's mind.
"They're beautiful!" was all Aaron could say in reply.
"That's why I invited you over Aaron. I know that you like to fuck asses just like I do. I knew that when I spoke with Edna," Mack told him.
"Oh yeah he does have a nice ass," Aaron replied and then added, "But Edna was supposed to be discreet."
"Don't be upset with Edna. I set the whole thing up to see if you were game. You know when it comes to mouths and asses all holes are equal. It doesn't matter if it's a guy or girl. I know you can appreciate that which is why I do business with you and why I invited you here," Mack told him.
"Hey, cheers!" Mack said raising his glass to Aaron and changing the topic.
Aaron returned the toast, "Cheers!" and he lifted his glass to Mack.
"Come on bring your drink and I'll show you the place while Mali and Tola get dinner ready," Mack offered.
Aaron picked up his drink and followed Mack around the house. Aaron was obviously impressed with the house and décor. Mack showed him the first floor and lower level as there were only bedrooms and baths on the second level. On the main floor was the living room, dining room, library, den, kitchen, breakfast area, a gathering area and two bathrooms. The lower level was really interesting where there was an exercise area, bar, game room, two more bathrooms and a room Mack called the relaxation room. The relaxation room had a large Jacuzzi that measured 8'x8'. It also had several lounge chairs and tables, a couple of massage tables and a large soft mat on the floor.
"I have a lot of fun in this room with Mali and Tola," Harrison remarked to Aaron.
Aaron felt his cock swell just from the thought of being naked in the relaxation room with Mali and Tola. He imagined Mack in the Jacuzzi naked with his two housekeepers and then getting a massage from them. He wondered if Mack ended up on mat fucking the two of them. Mack told Aaron that outside there was a swimming pool and another Jacuzzi, a cabana and plenty of lounge chairs. Mack told Aaron that it was very private and that he often swam in the nude outside. Then Mack took Aaron back upstairs to check on dinner.
Tola told them that dinner was ready to be served so Mack and Aaron took their seats at the dining table. Mali opened a bottle of wine and Mack gave his approval after tasting it. Mali and Tola then brought the food out from the kitchen and served Aaron and Mack. Aaron could not take his eyes of Mali and Tola as they moved around the table and made several trips to the kitchen. He constantly caught glimpses of their bare legs through the slits in their skirts but it was their shapely asses that he salivated over.
Aaron was surprised but pleased when Mali and Tola sat down at the table to dine with them. The meal was fantastic and Aaron enjoyed everything that was prepared. Mali and Tola guided Aaron through the Thai dishes and explained what sauces and spices to use. Mack cautioned him on one spice.
"Aaron, be careful with that one. It will burn the skin in your throat and scald the hairs in your nose," Mack said with a boisterous laugh.
Tola told Aaron that it was very hot and to try just a tiny bit. He moved over to Aaron and took a speck and placed it on Aaron's plate. As he did he pressed his breast against Aaron's arm then he smiled at Aaron as he moved back to his seat. Aaron tasted the spice as directed by Tola and Mack was right. Just that little speck set his mouth on fire. He quickly slugged down some wine as the other three laughed.
After dinner Mack and Aaron adjourned to the den and Mack poured then after dinner drinks. They chatted some more while Mali and Tola cleaned up the dishes. Mack never once brought up business and Aaron didn't dare. Mack had taken a liking to Aaron and it was obvious. Mack refreshed their drinks just as Mali and Tola came into the den. They stood there as if waiting for their next assignment.
Mack looked over at Aaron and asked, "Aaron, are you in the mood for a blow job?"
Aaron couldn't believe what he heard and stammered his response, "Did I hear you right, a blow job?"
"Yes you heard correctly. Mali and Tola give wonderful blowjobs and I know that they think you are very handsome," Mack told him.
Aaron blushed but replied, "How could I refuse an offer like that?"
Mali and Tola smiled and they walked over and knelt on either side of Aaron. He slid forward in the chair as they unbuckled his belt and unfastened his trousers. Aaron then lifted his hips as they tugged his pants and underwear down past his knees. Aaron was already hard when his cock came into view. It sprung up when his underwear cleared his pubes and he heard gasps from Mali and Tola.
"They like your cock Aaron. This will be a real treat for them as well," Harrison said.
"What about you Mack, aren't you going to get one too?" Aaron asked.
"No not tonight. I'm not young anymore like you. So I want to save myself for when we fuck them later," Mack replied.
Aaron watched as the two delicate mouths moved up and down on the side of his shaft with their lips pressed together. The slit skirts spread out and Aaron could see an ample amount of leg flesh showing. He was really turned on and he knew that it would take everything he had to control an early ejaculation. Tola wrapped his hand around the base of Aaron's cock and tightened his grip. It was like having a cock ring around his balls. Tola held Aaron's cock in one hand with Aaron's ball sac resting on Tola's thumb. Tola held Aaron snugly and as a result the ball sac was stretched tight.
Tola then began to lick Aaron's tight ball sac and at the same time Mali lowered his mouth to engulf Aaron's cock. Aaron wanted to reach down and grab both pony tails as they worked on his cock but he thought better of it. Instead he just watched as the two beauties worked over his cock and took turns sucking it. Aaron then felt his balls really tighten as his orgasm built in his loins. Tola seemed to sense his pending ejaculation and he covered Aaron's cock with his mouth.
Aaron groaned as he came and filled Tola's mouth with cum. Tola took the first two streams in his mouth and then he passed the cock to Mali to receive the next burst of cum. Mali took a couple a shots and then passed it back to Tola. The two of them passed Aaron's cock back and forth until he was drained of every drop of cum. Mali and Tola were extremely efficient as not a single drop of semen was missed. Aaron just leaned back in the chair and groaned as he watched the two ladyboys kiss and share cum between them.
"Well done Mali, well done Tola," Mack complimented them and then he said, "Come on Aaron, tidy yourself up, grab your drink and we'll head down to the relaxation room."
Aaron pulled his pants back up and followed Mack to the lower level. Aaron's head was spinning as he couldn't believe the incredible blow job that he just received from the two beauties. He had forgotten all about Mack sitting in the den watching them. It was the first time that two people sucked his cock at the same time and the first time a client watched him get sucked off. It had been wild.
"I thought we would hit the Jacuzzi and then get a massage from Mali and Tola. Are you up for that?" Harrison asked.
"Sure that sounds great," Aaron babbled.
"Good you can put your clothes over there. Bring your drink with you," Harrison instructed.
Aaron knew he didn't have to ask about a bathing suit as it was obvious they would go in the Jacuzzi naked. Aaron wondered if Mali and Tola were going to join them in the Jacuzzi and he soon had his answer. Aaron and Mack were already in the water when Mali and Tola entered the room. They were both wearing silk kimono like robes and Aaron hoped that they were naked underneath. Aaron stared at them as they turned their backs to him and dropped their robes. They were naked as Aaron had hoped and their beautiful shapely bodies were on display.
Aaron took in their beauty from head to toe. He admired their slender shapely legs as his eyes traveled upward to their buttocks. He stared at their incredible curvy asses which looked perfect. Their waists were narrow and their skin was flawless. Mali and Tola released their ponytails and their black hair draped over their shoulders. Aaron's cock was rock hard by now.
Then Mali and Tola turned around and faced Aaron and Mack. Aaron looked at their pretty faces and small but perfect tits briefly. Then his eyes dropped and looked at their dicks. Mali and Tola were pretty ladyboys and they had cute cocks.
"Aren't they something?" Aaron heard Mack say and then, "Aaron I would have never shared this with you if you hadn't fucked Edna. I thought you would really like Mali and Tola. Wait until you fuck them in the ass; you've already experienced what good cock suckers they are."
Aaron kept staring at the pretty boys somewhat in disbelief but at the same time in admiration of their incredible effeminate bodies. They were such a contrast to Edna. Mali and Tola then walked toward Aaron and they entered the Jacuzzi. The little cocks hardened and Aaron noticed that they were even small when erect. Mack was also hard now and Aaron noticed that he had an average size cock. Mali and Tola stood close to Aaron and ran their hands over his body. They lifted his balls and stroked his cock as they pressed their tits into his body. Then Tola moved over to Mack and she began to stroke him as well.
They stayed in the Jacuzzi for several minutes engaging in foreplay until Mack announced it was time for a massage. Aaron and Mack got out of the water and Mali and Tola dried them with large fluffy Turkish towels. Aaron and Mack then stretched out on the massage tables as Mali and Tola retrieved the body oils. Mali then massaged Aaron as Tola massaged Mack. Mack and Aaron were face down as Mali and Tola worked the oil into them, first the shoulders, then the back, buttocks and legs. Mack and Aaron then turned over and their erections were sticking up in the air. Mali massaged Aaron's chest, abs and legs skipping his pubes. Then she returned to is pubes and she lovingly stroked his cock. Aaron knew he would cum if she kept it up. Just then Mack spoke.
"Okay, let's go to the mats. Aaron I'm going to fuck both asses first and loosen them up for your cock," Mack stated.
Mali and Tola took up the subservient doggy-style position on the mats as Mack lubricated both assholes. Aaron was dying to get his cock into one of their asses as he watched Mack prepare them for anal sex. Mali and Tola had their heads down turned toward each other. They reached out and held hands as Mack worked on their asses. Then Mack moved behind Mali and eased his cock into the shapely ass. Mali groaned with the anal penetration and squeezed Tola's hand tightly. Mack didn't fuck Mali for very long and then he moved over to Tola and began fucking him.
"Mali is ready for you now Aaron, but take it easy," Harrison told Aaron.
Aaron moved quickly behind Mali and lined up his cock with Mali's asshole. He pushed in and found the fit to be very snug but his cock steadily entered Mali's ass. Mali grunted as he felt the larger cock make its way into his ass. Mali placed a hand on Aaron's thigh as a reminder to go slow.
"Oh Tola!" gasped Mali.
Aaron began to fuck Mali slowly and each time he moved forward his cock went a little deeper. Mali moaned and groaned each time the cock went deeper and touched new areas in his rectum. Soon Aaron had his 7+ inches buried in Mali's ass. Aaron loved the way Mali looked on all fours. Mali looked submissive and delicate as Aaron's thick cock reamed his ass. Aaron was close now and he knew that he was going to shoot an enormous load in Mali's ass. Aaron thrust all the way in and groaned out loud as he came in Mali's ass. Jets of cum shot into Mali's ass and quickly filled his rectum to overflowing. As Aaron resumed fucking Mali, cum ran out of Mali's ass and down over his balls. Mali's anal muscles were working furiously milking Aaron's cock.
Aaron pulled his cock from Mali's ass and watched as cum oozed out and ran down between Mali's buttocks and over Mali's tiny balls. Aaron had forgotten all about Mack and Tola next to him. Mack had finished fucking Tola but Mack did not cum as he was saving himself for later. Mali and Tola collapsed on the mat, cuddled and kissed. Then Tola rotated his body and Tola and Mali sucked each other's cock. Aaron was still hard and Mack marveled at Aaron's stamina.
"It looks like your still up for another round. Take Tola's ass this time," Harrison directed.
Aaron got behind Tola at the same time that Mack got behind Mali. Aaron fucked Tola's ass as Mack fucked Mali's ass while Mali and Tola sucked each other's cock. It was a fantastic group sex experience and it was incredible. It took Aaron longer to cum this time but when he did he flooded Tola's ass just as he had with Mali. Mack also came this time and dumped his load in Mali's ass. Aaron removed his cock from Tola's ass and Mack pulled out of Mali's ass. Tola and Mali stayed in the 69 position and continued to suck each other's cock until they both ejaculated.
Mack and Aaron moved over to the lounge chairs at Mack's direction and they watched Mali and Tola pleasure each other. Aaron was still amazed how much they looked like girls and beautiful girls at that. After Mali and Tola separated they returned to the Jacuzzi and allowed the jets to cleanse their bodies. Then they dried off and put their robes back on. Mack told them to refresh the drinks and they left the room.
"So Aaron what do you think of my ladyboys?" Harrison asked.
"Absolutely fantastic, I love them," Aaron answered.
"Aaron, why don't you stay the night and I'll have the boys freshen up your clothes," Mack suggested.
"Really, I'd love to."
"Sure I have plenty of room and I know that Mali and Tola would like more of your cock. We can have some more sex in the morning and then we can talk business over breakfast before you leave."
"Sounds good to me," Aaron exclaimed.
Just then Mali and Tola returned with the drinks. They served Mack and Aaron and then left the room. Aaron and Mack were still naked and they sat around drinking and talking as it was the most natural thing in the world. Aaron was thrilled to be in Mack's company and Mack really liked the young adventurous Aaron. They finished there drinks and Aaron went to pick up his clothes.
"Aaron leave them, the boys will take care of them. Come on I'll show you to your room," Mack told him.
They both walked upstairs naked to the bedrooms and Mack showed Aaron the guest room. Aaron was surprised to see that the guest room had its own bath.
I'll send the boys in and they will turn down the bed and get you anything you need," Mack told him and then said, "Goodnight, I hope you sleep well."
Mack left the room and then Mali and Tola entered. They turned down the bed covers and Aaron watched them closely. As Tola was leaning over the bed Aaron ran his hand over Tola's ass. Tola looked over his shoulder and smiled then Tola dropped his robe and continued working on the bed. Aaron got the message and he played with Tola's ass. Aaron fondled the pretty buttocks and fingered the tight anus. Aaron felt his cock harden and he rubbed it over Tola's buttocks. Mali then dropped his robe and got in bed on all fours.
"We all fuck, okay?" Tola said.
"Okay," Aaron gasped.
Tola got behind Mali and slid his cock into Mali's ass. Then Aaron got on the bed behind Tola and put his cock in Tola's ass. Tola did all the work as he thrust into Mali's ass and impaled his ass on Aaron's cock. Tola picked up the pace in search of his own orgasm and as he did he drove Aaron toward another one as well. Aaron stiffened and came for the fourth time that night and he knew that he was done. His cock slipped from Tola's ass as he went soft faster this time. Tola came in Mali's ass and then Mali turned around and sucked both Tola's cock and Aaron's cock dry.
Mali was now hard so he fucked Tola's ass. Aaron watched the two of them fuck right next to him in the same bed. After Mali came, Tola turned around and sucked Mali's cock. Aaron was in awe of how beautiful the two of them looked together. Mali and Tola then got out of the bed and put there robes back on. They said goodnight to Aaron and bowed slightly as they left the room. Aaron lay in bed thinking that he could get used to a life like this. He thought it might be cool for him to have ladyboy housekeepers. Aaron then dozed off in one of the most comfortable beds he had ever been in.
MORNING AT THE HARRISON HOUSE
Aaron woke up early with his bladder about ready to burst. He went into the bathroom took his morning piss and then he returned to bed. He had no trouble falling back asleep and within minutes he was in a deep sleep. Aaron had a wonderful dream that he was surrounded by pretty girls and ladyboys and they couldn't get enough of his cock. In the dream his cock seemed to stay hard forever as he fucked countless pussies, mouths and assholes. Aaron slowly woke up to find Mali and Tola naked in bed with him sharing his cock.
Just as they had done in the den last night they took turns sucking his cock. When Mali sucked his cock, Tola licked his balls. Then Mali passed off Aaron's cock to Tola who took it as deep as he could. Mali ran his fingers over Aaron's scrotum and lightly scratched his perineum. Aaron blew his load without warning and Tola calmly swallowed the first several discharges. Tola then passed the cock to Mali who received the next series of cum shots and then he passed it back to Tola. Tola sucked some more and then the cock went back to Mali. Aaron was beside himself with the eroticism of the moment. Finally with his cock sucked dry, Tola and Mali kissed as they had done the last time. Aaron lay back in bed and watched as the two beauties kissed and shared cum between them. Then they broke the kiss and smiled at Aaron.
"Mr. Harrison say you get up now for breakfast. We fuck later," Mali told him as Tola nodded, smiled and said, "Here clothes."
Then Mali and Tola left the room. Aaron got out of bed and took a quick shower and then dressed for breakfast. He noticed that his clothes had been cleaned and pressed. Aaron made his way down to the breakfast area where Mack was already there reading the morning newspaper. Aaron noticed that Mack was reading the financial section.
"Good morning, how did you sleep?" Mack asked.
"Like a rock it was the best night's sleep I had in a long time," Aaron told him.
"Good, how was your wake-up call?" Mack asked with a snicker.
"The best," Aaron replied with a laugh and then said, "You know hotels could do very well offering a service like that."
Mack laughed and said, "Have some coffee," as he pushed part of the newspaper toward Aaron.
Aaron poured a cup of coffee and then picked up the paper. Not another word was spoken until Mack finished reading the financial section. Then he addressed Aaron.
"Okay let's have some breakfast and then some fun. I have things to do after breakfast today so I have to send you on your way. By the way Aaron, if you ever want to have your own ladyboy, I have a contact in San Francisco who can get one for you," Mack offered.
With that said Mack called for Mali and Tola to serve breakfast. Mali and Tola brought out a sumptuous spread for breakfast and made eggs to order for Aaron and Mack. Aaron ate about six eggs as he wanted to be ready for more fun and games with Mali and Tola.
After breakfast Mack and Aaron put on a couple of terry robes and went out to the swimming pool area. They were both naked under the robes and sat in the lounge chairs drinking coffee and discussing Mali and Tola. Mali and Tola then joined them at the pool and they too were just wearing robes now and Aaron knew that they would be naked under them. Shortly thereafter, Mali and Tola shed their robes and then applied suntan lotion to each other's body. Aaron watched as they took turns covering every inch of the other one's body. Aaron got an erection and he put his hand inside his robe to stroke it. Mack noticed this and spoke to Aaron.
"Go ahead and fuck one of them if you want," Mack told Aaron.
Mali and Tola looked over at Aaron and smiled. "You come and fuck Tola first," Mali said.
Aaron stood up and dropped his robe on the lounge. He walked over to the two ladyboys with his erect cock sticking straight out. Tola got on all fours on the lounge chair and Mali lubricated Tola's asshole in preparation for Aaron's cock. The Mali lubricated Aaron's cock and lined it up with Tola's asshole. Mali held onto Aaron's cock so he wouldn't go too deep as he pushed forward. As soon as Mali felt that Tola's ass had loosened up sufficiently she let go of Aaron's cock. Aaron then went deeper into Tola's ass and fucked him with long steady strokes.
"You pull out this time," Mali said indicating that he didn't want Aaron to cum in Tola's ass.
Mali played with Tola's tits and Tola's cock as Aaron fucked Tola. Then Aaron felt his release build up in his scrotum and pulled his cock from Tola's ass. Mali took a hold of his cock and jerked it as Aaron fired streams of cum onto Tola's body. The first shot hit Tola in the head and left a trail from his hair down to his lower back. The next couple of shots covered Tola's shoulders and back. The final couple of shots landed on Tola's ass. Mali continued to jerk Aaron's cock and move it around on Tola's ass. Mali used Aaron's cock to spread cum all over Tola's buttocks and then Mali pushed Aaron's cock back into Tola's asshole. Tola then used his sphincter muscle to milk Aaron's cock dry.
"Wow that was some show!" Mack exclaimed as he stroked his cock and then called to Mali, "Come here Mali I need your mouth."
Mali went over to Mack and sucked Mack's cock until he came in Mali's mouth. Then Mali and Tola went into the swimming pool with Mack and Aaron. Mack and Aaron relaxed in the water as Mali and Tola played with each other. At one point Tola sat on the side of the pool while Mali sucked Tola's cock. Then they changed positions and it was Tola's turn to suck Mali's cock. This got Aaron hard again and he wanted to fuck Mali this time.
Aaron put a rubber raft in the pool and he had Mali lay flat on it face down. Aaron pulled the raft into the swallow end where he could stand with his cock out of the water. Aaron then had Tola lube Mali's ass with lotion as Aaron applied the lotion to his cock. Aaron moved closer to Mali and eased his cock into Mali's ass. Aaron fucked Mali slowly and used the raft to push and pull Mali back and forth. It was an erotic scene and it caused Aaron to cum quicker then he normally would have under the circumstances.
Tola realized that Aaron was close to cumming so Tola pulled Aaron's cock from Mali's ass and held it under water. Tola felt Aaron's cock throb and pulse as he ejaculated into the pool. Jets of semen flew out of Aaron's cock and formed into milky cloud under the water. It was incredibly erotic to see cum shooting under water. Tola used his fingers to play with the milky cum in the water and giggled as he tried to pick it up. Tola continued to jerk Aaron's cock and then he leaned over and took Aaron's cook in this mouth. Tola sucked Aaron's cock dry and Aaron knew he was done for awhile. Aaron got out of the pool, dried off and then sat naked in the lounge chair. Mack, Mali and Tola also got out of the pool and sat naked in the lounge chairs. Aaron excused himself to go get dressed as he knew it was time for him to leave.
Aaron returned to the pool and thanked Mack for a wonderful time. Mack nodded and reminded Aaron of the need to be discreet about the new relationship. Mali and Tola smiled and waved goodbye as if they were two little nymphs. Aaron left the property and then drove home. He thought about Mack's contact in San Francisco and wondered how it would work getting his own ladyboy. Aaron figured that it would be an expensive proposition. He dismissed it as he thought about his sex life. He had Edna in the office and he had no trouble getting dates on the weekend. A ladyboy might just complicated things at that time. He decided to call Jill and see what she was up to for the rest of the weekend.
JILL COMES AROUND
Aaron called Jill when he got home and she was thrilled that he called. They went out on Sunday to a place that had dancing as well as dinner. They enjoyed a wonderful meal and then danced late into the evening. As they were dancing Jill warmed up to Aaron and he was excited as he had never been able to get Jill in bed yet. Jill cuddled as close as she could get. Aaron began to kiss her neck and nuzzle her as they danced and then at the end of each dance they kissed on the lips. It was getting late and then Jill asked Aaron if he was going to invite her back to his place. There was only one answer and they headed to Aaron's condo.
When they got inside the condo, Aaron turned Jill toward him and French kissed her plunging his tongue in her mouth. She kissed him back with enthusiasm and he steered her over toward the bedroom. Aaron lowered the top of Jill's dress to her waist and bared her nearly flat chest. Jill had tiny boobs but she had hard little nipples that stuck out about an inch. Aaron sucked on her nipples and she loved it.
Jill called out to me as I was sucking her nipples. "If you want big boobs you know that I haven't got them."
I stopped sucking her nipples long enough to reply, "Don't worry I am a leg and ass man. I am not into big boobs."
Jill was thrilled and that night she couldn't wait to get Aaron's cock in her pussy. He went back to sucking her nipples and then he finished undressing her. The dress fell around her ankles and she flopped back on the bed. Aaron eased her pantyhose off her and then her panties. Jill had a cute pussy with a little tuft of brown hair above the opening. She was dripping wet when Aaron slid his tongue across her labia and then worked it into her sweet passage. Jill stiffened and came with a mild orgasm as he slipped his tongue in and searched for her hooded clit. Jill screamed out loud when his tongue touched her clit. Then Aaron pushed her legs further apart and spread her lips open with his fingers. Her erect clit was standing straight out and he bit it lightly with his teeth. Jill jumped with pleasure and moaned loudly. Aaron continued to lick and nibble her clit until she lost it and sprayed his face with her female love juice. Jill tired to push him away but he held her hands firmly and pressed his tongue into her twat. Soon she was pleading out loud for Aaron to stop that she couldn't take it any longer.
He stood up and removed all of his clothes as Jill lay on the bed recuperating. Jill looked at his hard cock as Aaron approached her and he could see she was pleased. He moved between her legs and slid his stiff cock in her pussy. She was a little snugger than Aaron thought she might be and he was happy that she could feel his cock on her vaginal walls. Aaron started fucking her slowly but then he needed to cum and he picked up the pace. Jill fucked back at him throwing her pussy up at him as he plunged his cock deep in her hole. They were both fucking frantically now and racing toward their mutual orgasms. Aaron was out of control as his seed flew out of his cock and splashed against Jill's vaginal walls and deep into her pussy. She strained as she too had another intense orgasm and she worked to keep her clit in contact with his cock. They started to move slower as they regained their composure. They were dripping wet with perspiration.
The two of them rested in each other's arms and Aaron stroked Jill's body. He loved the touch of her skin, her shapely legs and curvy sexy bottom. Jill loved to have her pussy played with constantly then she would get aroused and either she would mount him or he would mount her and then they would fuck again until she orgasmed. Jill orgasmed countless times that night and she seemed insatiable. After Aaron's third ejaculation, which was always a stretch for him, he had to resort to his fingers and tongue. They eventually fell asleep in each other's arms.
In the morning Jill was ready to go again and Aaron was thankful for his early morning piss hard-on. He could always last a long time before he took his first piss in the morning so he was able to fuck Jill through multiple orgasms satisfying her needs. Aaron got up and left her lying on the bed drained from the intensity of her climax and he went to the bathroom to relieve himself. When Aaron returned to the bedroom Jill was playing with her pussy again and he was ready to get off. He crawled between her legs and slipped his cock back in to her wet pussy and they fucked until they both came again. Aaron shot wads of cum into her that morning and he was surprised with the volume and force of his ejaculation. They then showered, dressed, ate a light breakfast and then departed the condo. Jill went directly to work and Aaron headed off to his office.
EDNA'S NEWS AND JILL'S ACCEPTANCE
That Monday morning Aaron arrived at work and he was greeted by a bubbly and excited Edna. Edna had been hired to work as a female impersonator at a San Francisco club. Aaron was pleased for Edna but now he would need a new assistant. To celebrate Aaron fucked Edna in the ass and then they discussed the time frame of Edna's departure. The club wanted Edna to start as soon as possible and Edna was anxious to begin the new career. Aaron said that Edna could leave immediately and then they fucked once more as a farewell.
Aaron knew he would have to move quickly and then he remembered that Jill said that she did not like her job. Aaron asked Jill if she would be interested in working for him and she couldn't say yes fast enough. She was ecstatic and told him that she could start in two weeks. Aaron said that he would begin Jill's training in the evening at his office.
That week Jill would arrive at Aaron's office and go through about three hours of training. Then they had sex together before Jill returned to her own apartment. The following two weekends they didn't leave Aaron's condo. They had continuous sex and stayed naked for the majority of the time. Jill loved being naked and displaying her lithe body. Even when they watched television or a movie she wanted her pussy played with constantly. It was that weekend that Aaron also started playing with her ass.
Jill liked her ass fondled and the anal intrusion of Aaron's finger. He always greased her asshole with lube and then fingered her ass as he played with her pussy. Aaron fingered her asshole every time that he ate her pussy. He also fingered her bum when he fucked her doggy style. One time when they showered together, Aaron washed Jill's ass thoroughly pushing his soapy fingers deep into her rectum. After their shower he had Jill get on the bed on all fours and he licked her pussy from behind. Then he moved his tongue up to her nether hole and teased her with the tip. Aaron continued to lick and probe both her pussy and asshole with his tongue and Jill went absolutely wild. She had one of the most intense orgasms Aaron ever saw her have just from the cunninglus and anal stimulation.
I told Jill about his first assistant Cathy and how that was his first time rimming anyone. Jill was intrigued with Cathy's passion for anal sex and she admitted that she had often thought about it but had never tried it. Jill told Aaron that she trusted him and that if he wanted to try it with her that she would. Jill had a perfect bubble ass for butt fucking as it was round and smooth and perfectly contoured for her lithe body. Aaron told Jill that they would work up to it and that he would introduce her to anal toys and stimulation that would loosen her up and bring her pleasure. Aaron was really anxious to fuck her ass but he did not want to injure her or scare her away.
As Jill settled in to her new role they continued to have torrid sex and Aaron introduced her to more and more anal pleasures. He kept adding toys to their relationship and the ones she enjoyed the most were the anal beads and a vibrating dildo. The first time they used the anal beads Aaron thought she was going to pass out. He ate her pussy and he popped one bead out of her ass at a time as she orgasmed until all six beads were removed. Jill screamed out loud and her body went into convulsions with the intensity of her climax. Jill also loved the vibrating dildo in her ass as Aaron fucked her pussy doggy style. As she became accustomed to the beads they increased the size of them and they would keep increasing the size each time she became comfortable with the intrusion. They had reached the point were we felt she was ready for Aaron's cock.
JILL'S BIG STEP
One evening Aaron fucked Jill and ate her pussy until she had multiple orgasms and she was totally relaxed. He rolled her over and had her kneel on all fours on the bed. He used his fingers to lubricate her ass putting plenty of the slick substance in her asshole. Jill cooed as Aaron fingered both her asshole and her pussy simultaneously. He placed his hand in the small of her back and pushed lightly so that Jill arched her back and accentuated her curvy ass. He was so ready to fuck her ass that his cock seemed harder than ever and throbbing in anticipation of taking her anal cherry.
Jill felt the thick head of his cock between her rounded buttocks and just outside her nether hole. She knew that it was finally about to happen and she felt her stomach turn with the thought of committing such a depraved act. Aaron put an ample amount of lube on his cock and then added his saliva to it making it as slippery as possible. Once he was satisfied that his cock head was slick enough he introduced it to the tight ring of Jill's anus. Jill looked back over her shoulder at Aaron as she felt him pushing his cock against that intimate part of her body.
"Please go easy, be gentle," she reminded me.
Aaron slowly pressed against her tight opening and noticed that Jill was holding her breath. He told her to relax and breathe deeply as he continued pressing forward. Jill felt the initial thrill of her sphincter being forced open by his thick cock and her first response was to try and avoid the anal invasion. Aaron held her hips and he continued to push forward past her resisting body. Jill's mouth gaped open and she grasped the bed sheets in both hands as his cock head cleared her sphincter and lodged in her anal channel. Jill unintentionally flinched and caused more of his cock to slide inside. She cried out.
"Are you okay?" I asked.
Jill nodded and then she once again reminded Aaron to go slow. He gave her a few seconds to recover and then pressed forward again and her flower opened up for him. She just needed a few minutes to get used the unfamiliar sensation of being so filled from behind. Jill then responded unexpectedly as she accepted his cock in her ass. She pushed her butt back toward him and then moved forward. She did this for awhile and it seemed as if she were accepting and rejecting his cock at the same time. Finally Aaron's cock was buried to the hilt in her ass and they began moving together. He felt his balls slap against her pussy each time he thrust into her hot ass.
"Oh, this is so sexy. It feels so good but I feel dirty at the same time. If my parents could only see their precious daughter now," Jill murmured.
Jill had been raised by very strict parents and she had always been taught that pre-marital sex was taboo and dirty. Aaron also wondered what her parents would say if they could see their daughter with a 7+ inch cock in her ass. Jill's lust took over and she rolled her ass in tiny circles as she was consumed with her first anal fuck. Aaron looked down at her firm buttocks and he marveled at the way his thick shaft stretched her nether hole. He tried to imagine Jill's parents, whom he had never met, standing on either side of her watching as her asshole opened and contracted around his cock.
Jill reached between her legs and into her puffy cunt. Her juice was oozing from it and she rubbed her stiff and aroused clit. Aaron picked up the pace and began to fuck Jill's ass with steady full thrusts. She gasped at the new almost unbearable sensation surging through her rectum. There was no pain now but just a glorious feeling of being stuffed with cock. She felt full and a little bloated but the pain had disappeared quickly and the bloated feeling was gone also. Jill loved the taboo feeling of being filled with cock in her ass. The thought of this forbidden act along with her clitoral stimulation pushed Jill closer to yet another climax.
Aaron was trying to hold off his threatening ejaculation as Jill's movements intensified with her pending orgasm. They were both perspiring and Aaron held to Jill's shapely buttocks as he slowed his pace slightly in an effort to slow his eruption. Jill groaned loudly as her head dipped down to look between her legs and she pushed back in an effort to get more of his cock in her.
"Oh Aaron, fuck me. Fuck me in my ass, it's so good so wicked, I love it," Jill cried out.
Jill was going wild with his cock in her ass and he had never seen anyone take to anal intercourse with such abandon for their first time. Jill balanced herself on both hands as she thrust backward impaling her ass on his thick cock. Aaron knew that he could not hold out much longer. He reached around with one hand and found Jill's pussy and engorged clit. With the other hand he pinched the rock hard nipples sticking out from her flat chest. Her clit throbbed as it clamored for attention and her pussy clenched his fingers as it released her warm love juice. The points of her nipples were excited beyond desire and his cock was clamped in her well stuffed bottom.
Jill was out of control as all she knew at this point was that she was being fucked up the ass with a very thick cock and it felt fantastic. She was on the verge of her most intense orgasm ever and she struggled frantically seeking her climax. A few more seconds of rubbing her stiff clit sent Jill into a mind blowing orgasm. Her body stiffened and then spasmed out of control as she moaned loudly and struggled to breathe. The intensity of her climax was too much for Aaron and he grunted as he shot his spunk into her forbidden tunnel. Jill's eyes flew open in surprise as she felt his hot thick semen rush into her rectum and splash off her bowels. Her face was pure ecstasy as she turned to look at Aaron as his cock continued to spurt its sticky fluid up into her.
"Give it to me, cum in my ass, oh I can feel it. it's so good so nasty," Jill cooed as she was overcome with passion
Jill fell forward on the bed as Aaron continued to marvel at the beautiful ass that he had just deflowered. As she lay before him she clenched and unclenched her ass muscles causing cum to ooze out of her asshole. It looked like a small spring as the semen intermittently bubbled up and trickled out of her ass between her ass cheeks and over her puffy pussy lips. Aaron stayed hard and stroked his cock as the last tiny drops landed on her ass. He then realized that he was going to stay hard and he decided to try and fuck her ass again.
Aaron told Jill that he wanted to fuck her ass again and in an almost business like fashion she pushed her self back up on her knees. She turned her head to the side and smiled at him waiting for the second penetration. He pushed his still erect slippery cock into Jill's now gooey asshole. Jill felt her sphincter being stretched again but this time she welcomed the sensation of her ass being filled with his thick cock. As he pushed inside her his spunk from the previous ejaculation was squelched almost obscenely with his cock. His previous deposit squeezed out around his shaft and oozed from Jill's asshole running down between her buttocks and plopping on the bed sheets.
Jill was an extremely hot woman and her fucking technique was incredible. Aaron stayed crouched behind her and placed his hands back on her hips as he fed his long thick cock deep into Jill's accommodating back passage for a second time. Jill pushed her hips back at him and her bodies slapped loudly together.
"Yes, yes, oh I love it. Fuck my ass with your hot cock," Jill yelled to him and then she cried out, "Make me cum again fuck my ass with that big cock."
As before Jill lowered her head to the bed and turned it to the side as she grasped the bed sheets. But this time she grabbed the sheet in the thrones of passion and not because of apprehension. Aaron could feel her taut muscles massaging his shaft in her ass as he held on to her slim waist and he caressed her curvy firm ass cheeks. Her sphincter grabbed the base of his cock as she worked her lithe athletic body. Jill was an incredible sex partner who had just turned into a fantastic ass fuck. Aaron knew that he was getting close to losing it again as Jill manipulated his pecker with her undulations and sphincter muscle and that he would soon be adding more semen to join his previous load in her ass.
Jill had her hand back on her clit and rubbed herself frantically as she had another violent orgasm thrashing and panting wildly. He felt his seed travel along his scrotum and then spurt into the recesses of her ass. Jill felt the second ejaculation shoot into her bottom and she wallowed in the feeling of the warm liquid once again soothing her ravaged ass. Jill squeezed her sphincter muscle extracting every drop of cum from his cock until he went soft and slipped from her hot gooey ass with an audible pop. Jill collapsed face down on the bed and savored the moment. She knew now that she was hooked on anal sex and that she could expect to be ass fucked regularly from now on. Aaron flopped next to her and held her to him as they kissed and rested.
"I never thought that I could get so turned on from anal sex. It was incredible I felt like I would never stop cumming. The feeling of your hot semen shooting into my ass was unbelievable. I never expected it to feel so good just from being so full," Jill murmured as they lay together.
"I am so glad that you liked it as you know I loved fucking your ass," Aaron replied.
Jill then cuddled back up to him and they dozed in each other's arms. Later they had vaginal sex as Jill rode his cock until she came and collapsed on him as he shot another wad in her pussy this time. For the next two years Jill and Aaron would have a very steamy relationship.
JILL ENJOYS SEX IN THE OFFICE
Jill loved having sex in the office. She would lock the office suite door and then come into Aaron's office. Jill would then pretend to show him something important and she would come around to his side of the desk and lean slightly forward. Jill always wore mini skirts that showed off her shapely legs and blouses or sweaters that ended at her narrow waist. Aaron slid his hand up her leg and he felt her tremble slightly as we had played this game before and she knew where it was going. He let his hand ride up and down her stocking covered leg for a few minutes. Then he let his hand wander above her knee and past the top of her elastic top hose. Jill shivered as his hand touched the bare skin of her thigh. Aaron caressed both of her thighs and he could tell that she was getting hot. The back of his hand brushed against her panty covered pussy and he could feel that the panties were soaked with her excitement. Jill moved her legs wider apart causing the skirt to tighten around her shapely ass. Aaron rubbed her inner thighs between her legs and flicked his fingers over the material covering her vulva. Jill jumped involuntarily when she felt his hand on her pussy.
"Your panties are very wet Jill. Would you like me to take your panties off you?" he teased her.
Jill nodded and gasped, "Yes, please take my panties off."
Aaron eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Jill stepped out of them and he put them on his desk. He returned to fondling her ass and thighs and he soon had her squirming with desire. Jill moved her body as if she were trying to get Aaron's hand near her pussy so he slid it between her legs and stroked the outer lips of her labia. Jill squirmed under the touch an emitted a soft groan. He started to push Jill's skirt up but she stopped him and then she took it off. It was a wrap around mini and she had it off in an instant. She looked so sexy standing there leaning forward slightly over his desk. Her cute ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.
Aaron ran my hands all over Jill's ass, thighs and pubes feeling her wet pussy. He slipped his finger into her vagina and then added a second one. He took some lotion from his desk and he pushed a finger between the cheeks or her ass and massaged into her nether hole. Then he fingered Jill's ass and pussy at the same time. She was going wild with the double penetration and cried out to him.
"That's it finger me, play with me. Make me cum, please make me cum," Jill pleaded.
Aaron continued to work her ass and pussy and within minutes she had her first orgasm. Jill held onto the desk with both hands as her body jerked and spasmed with her climax. He worked his fingers in and out of her holes as she clenched and relaxed her vaginal and anal muscles tightening herself on the digits. He pulled his fingers from her holes and he stood up behind her. Aaron dropped his pants and boxers to his ankles and brought his rock hard cock to her buttocks. He let it rest against the hot flesh of her ass and he leaned over and whispered in her ear.
"Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" he teased her and then licked her ear.
"Fuck my pussy first and then my ass. I want you to cum in my ass," Jill murmured.
Aaron then eased his cock into her pussy and fucked her from behind until she had another orgasm. Then he moved his cock to her ass and fucked her for a short time before he unloaded his semen in her anal canal. Jill looked so hot leaning over the desk with his cock sliding in and out of her asshole that he just couldn't prolong my ejaculation any longer. He leaned over her and she milked his cock dry until it softened and popped out of her ass.
Their sexual encounters in the office usually ended up the same way, with Aaron cumming in Jill's ass but only after she had cum herself two or three times. Jill would surprise him from time to time. One day she leaned over the desk and as he ran his hands up her legs he discovered that she had already removed her panties. Another time she just walked in without her skirt and panties looking very hot in just her hose and blouse. Once she brought one of the dildos with her and put it in her pussy so that when Aaron took off her panties he would find it. Jill liked being fucked in the ass and having her pussy filled with the fake cock.
Jill eventually moved in with Aaron and they had morning sex before they left his condo. On the way home from the office Jill would remove her panties and Aaron played with her pussy. Once they reached the condo they were both very hot and they went inside and fucked like rabbits. Jill had really adapted to anal sex and Aaron came in her ass at least once a day. She still loved the anal toys as well especially the beads. Jill picked up a unique dildo that had two cock heads on a handle. It looked like a big letter Y. Jill would put one cock in her pussy and the other in her ass for double penetration. Sometimes they would be in a 69 position and she would suck Aaron's cock as he double fucked her with the dildo. Jill went wild and juiced all over the fake cock as Aaron filled her mouth with cum. There seemed to be no end to her creativity and willingness to try new things although she had no interest in bringing other sex partners into their relationship.
TWO YEARS LATER
Jill received a great job offer and it made sense for her to take it. Aaron and Jill continued to live together but Aaron needed a new assistant. He decided to call Mack to see if he knew of anyone. Mack suggested that Aaron could have one of his lady boys.
"That won't work Mack. I'm living with Jill and she wouldn't want someone as pretty as Tola or Mali in my office," Aaron responded.
"Hey no problem they can just dress like young men. They ask about you all the time anyway. It would be a good way for them to earn some money in addition to the allowance I give them," Mack suggested.
"That could work, as long as they looked like young men. Which one do you suggest I hire," Aaron asked.
"Hire them both but you only have to pay them what you would pay one assistant. Hey I just thought of something. Hire them as husband and wife and then Jill won't suspect anything," Mack offered.
"That's a great idea," Aaron replied and then asked, "When can they start?"
"Tomorrow if you want, they don't drive so they will be taking public transportation," Mack advised.
"Tomorrow is great. I can also pick them up and drop them off on certain days," Aaron added.
"Consider it done," Mack said concluding the conversation.
Aaron hung up the phone and he was excited about having Tola and Mali work for him. He thought of all the possibilities with those two beautiful ladyboys. Aaron had missed them since Jill had moved in with him but now he could renew his action with those two hotties. Things had slowed down with Jill as they do in most relationships so Aaron should have plenty of energy for the ladyboys. Life was good!