tagTranssexuals & CrossdressersDevin Learns About Trannys 03

Devin Learns About Trannys 03



Wednesday rolled around and Devin was as anxious as he could be. He could hardly wait for the end of the business day. He rushed home and changed into shorts and a tee shirt before heading over to Paula's and Carla's condo. When he arrived Lee was already there dressed as a school girl. Lee was wearing a paid skirt, white blouse with a red string tie, knee high white socks and saddle shoes. He was also wearing a blonde wig that completed his look of a school girl. Paula and Carla were dressed like Devin with shorts and tees.

Paula made the mock introduction, "Devin this is Lee. She goes to school at the local academy. Lee loves to be fucked in the ass and we told her how much you like to fuck girls in the ass."

Devin was hard in seconds which brought a smile to everyone's face. Lee walked by Devin and stroked the front of Devin's shorts. Lee then moved over to a chair and knelt on it facing the back. Paula moved over to Lee and lifted the uniform skirt and draped it on Lee's back. Devin stared at the shapely round ass encased in the cotton panty. Devin felt his loins stir at the erotic sight in front of him. Paula lowered Lee's panty to just below his buttocks exposing the super fine ass.

"Doesn't Lee have a lovely ass? You can touch it if you like," Paula said invitingly.

Devin moved over behind Lee and he caressed the lovely ass. The skin was smooth and flawless with no trace of body hair. Devin ran his hands all over Lee's buttocks and teased the tail bone and anus with his fingers. Devin noticed that the cotton panty still covered Lee's cock and balls and only the sweet ass was exposed. Carla moved close to Devin and pulled Devin's shorts and underwear down to just below his pubes. Devin's stiff cock leaped out and bobbed in front of him. Carla and Paula smiled at each other as they watched Devin's cock twitch as he continued fondling Lee's curvy ass.

Paula handed Devin a tube of lube and Devin liberally lubricated his cock and Lee's anus. Devin was incredibly turned on from fingering Lee's ass and he couldn't wait any longer. Devin stepped up and pushed his cock into Lee's ass. Devin's cock went in with ease and he began fucking Lee with slow steady strokes. Devin was charged but he didn't want to cum too quickly as he wanted to savor the time in Lee's fantastic ass. As Devin fucked Lee he felt that he really could be fucking a pretty school girl as the only skin visible was Lee's shapely bottom. Devin held onto the lovely buttocks as he drove his cock in and out.

"Oh yes, that's the way to fuck my ass. I love it. Cum in my ass, I want to feel it," Lee whispered excitedly.

As hard as Devin tried to make it last, he was overcome with desire and he flooded Lee's rectum with an enormous load. Devin announced that he was cumming and Lee felt the surge of warm sperm fill his passage. Lee loved to receive massive loads in his ass and Devin had delivered. Lee used his sphincter to massage Devin's cock and Devin felt as if he could stay in Lee's ass all evening and fuck him again and again. Devin resumed his movement but Paula stopped him and had him pull out of Lee's ass. Devin stepped back with his erect cock slick with his own seed and watched as Carla dropped the shorts and underwear. Carla's thick 8"cock looked threatening behind Lee's anus but Carla stepped up and pushed into Lee. The big dick wormed its way in and Lee uttered an audible grunt.

Devin and Paula watched intently as Carla fucked Lee with long powerful strokes. Each time Carla thrust into him, Lee's sweet ass cheeks jiggled. Carla nearly lifted Lee off of the chair with each powerful thrust. Lee was pleading with Carla to cum and fill his ass again. Devin, without even touching his cock, stayed hard all the time that Carla fucked Lee. One final thrust and Devin knew that Carla was cumming in Lee's ass. Lee moaned in pleasure and rotated his ass in circles as he used his sphincter to squeeze Carla's cock dry. When Carla pulled out his cock too glistened with semen.

Paula quickly moved into position and penetrated Lee with one steady plunge. Lee again groaned as another 8" cock filled his anal cavity. Devin and Carla watched with renewed interest as Paula fucked the petite Lee. Paula came quickly and Lee squealed with delight as another massive load filled his rectum. Paula pulled out and quickly pulled Lee's panties back up.

"I feel so full," Lee sighed.

"I know that's why I pulled your panties up so you drip cum all over the carpet. Now go to the bathroom and relieve yourself and then wait for us in the bedroom," Paula instructed.

Lee walked in a dance like manner wiggling his ass as he went into the bathroom. Paula led Devin and Carla into the bedroom and they all stripped and waited naked for Lee to return. Lee was still dressed in the school girl uniform as was Paula's plan.

"Now we will undress our little school girl and have some more fun," Paula announced.

Lee stood in the middle of the others as they slowly undressed him. First the panties came off and Lee's erect cock leaped out. Lee lifted one foot at a time as the panties were removed. The plaid skirt tented out in the front due to Lee erection. Carla and Paula removed the blouse and tie as Devin fondled Lee's buttocks under the skirt. Paula removed Lee's bra and noticed Lee's budding little breasts.

"Carla, will you look at this? Lee is developing titties," Paula said in surprise.

"I'll be damned," Carla reacted.

"It's a surprise. I have been taking female hormones," Lee admitted.

"Well you little devil, we had plans to transform you and you started on your own," Paula acknowledged and then added, "I have to taste these."

"Me too," Carla uttered.

Both Paula and Carla leaned in and took lee's breasts in their mouths. The sucked on the little mounds and got the nipples rock hard. Then they gently nibbled on the nipples teasing the hard nubs between their teeth. Devin continued to fondle Lee's ass and Lee moaned among the foreplay attention. Carla next removed Lee's saddle shoes and white socks. Finally the skirt came off and Lee was as naked as the others.

"Devin you got to fuck Lee first tonight so it's only right if Lee fucks you before we do," Paula announced.

Devin was told to lie across the bed so that Lee could fuck him while standing up. Lee took of his wig and tossed it over with the uniform and then got the lubricant. He applied the lube liberally to his cock and to Devin's asshole. Lee then moved in and eased his cock into Devin's ass. Devin was glad that Lee fucked him first with his 6" cock as it would prepare him for Paula and Carla. Lee began to slowly fuck Devin holding on to the back of Devin's legs.

Paula moved behind Lee and Lee knew what was to come next. Paula's cock entered Lee's ass causing Lee to remain still until Paula was in. Lee then resumed fucking Devin. He had his arms hooked behind Devin's knees and leaned over as he fucked him. Lee looked up and saw that Carla had straddled Devin and presented Lee with another hard cock. Lee immediately took Carla's cock in his mouth and began sucking it.

Lee's ejaculation snuck up on him and he shot a huge load into Devin's ass. Lee knew that he could cum several times and he remained in Devin's ass. Lee kept fucking Devin as Paula fucked him and he sucked on Carla's cock. Lee was in a euphoric state having a cock in his ass, another one in his mouth and his cock buried in an ass. Lee knew that it get any better than this and it was like a dream come true. Seeing that Devin was hard again, Lee took the cock in his hand and jerked him off.

Carla was the first to cum and lee accepted the load in his mouth. Paula was next and ejaculated into Lee's ass which sent lee over the edge. Lee shot his second load into Devin which seemed to trigger Devin's ejaculation. Lee stroked Devin's cock as he shot several streams onto his own chest. The four of them didn't move for several minutes and when they finally separated they were all still hard. The eroticism of the evening kept them charged and they were all ready for more action.

Paula had Devin and Lee lie face down on the bed side by side. Paula straddled Devin and Carla straddled Lee sitting on the back of their thighs. Paula and Carla penetrated the two fine asses in that position and the feeling was very snug. With their bodies pressed to the mattress Lee and Devin were being fucked soundly. It seemed that Paula and Carla fucked Lee and Devin for over an hour moving around and changing positions in the process. The final position found Paula and Carla in a pushup position keeping their weight off of Lee and Devin as they drilled them with their big cocks.

Paula pulled out and ejaculated on Devin's ass aiming the release at his anus. Devin felt the warm seed land on his anus and buttocks and then he felt Paula re-enter him. Carla followed suit and repeated the action with Lee. Paula and Carla let their cocks go soft in the shapely asses and then they rolled to the side. Lee and Devin were rock hard and Lee took the lead and swallowed Devin's cock.

Lee maneuvered his body into a 69 position with Devin who was faced with the choice to reciprocate. Devin took the cock in his mouth and he sucked Lee as Lee was sucking him. Paula and Carla were done fucking for the night but they played with Devin and Lee as they sucked each other. They caressed their asses and testicles and teased their perineum helping to accelerate their releases. Devin liked sucking Lee as he could get almost all of the cock in his mouth. They stayed with it until they both came in each other's mouth. Lee and Devin rolled to their backs and sighed as they too were done for the evening.

Paula suggested showers for everyone and then drinks. Paula and Carla showered first and put their tees and shorts back on. Devin and Lee showered next while Carla got the beers for everyone. The four of them sat in the loving room sipping beer and toasting each other on a great evening. Devin still surprised himself with his behavior. It had been less than a week when he hooked up with Paula and then Carla sucking his first cock and getting fucked for the first time. Now just four days later he was in an orgy. He had never had group sex with girls in the past and it was difficult to belief that he did it with trannies and a gay guy.

The four of them had a few beers and then Devin excused himself as he had to be at work early the next day. Devin left and returned to his own condo. He had the impression that lee would spend the night with Carla and Paula. Devin got home and made himself a stiffer drink and took it in his bedroom. Shortly after finishing his drink he was sound asleep.


After the orgy Wednesday evening, Devin decided that he needed some time away from Paula and Carla. He looked into a beach resort that was very exclusive and he booked a three day weekend. Devin took Friday off and checked in at the resort on that Thursday evening. He did not tell anyone where he was staying as he wanted complete separation from his current situation.

That Thursday evening Devin met a very nice couple at the bar. Bobbi and Sam Harris were staying at the resort and Devin was pleased that they had introduced themselves. Sam was a physical specimen at 6'2" and 195 pounds. Had bleach blonde hair and he was very fit and very tan. Bobbi was a cute blonde with curly hair down to her neck. She had a very nice figure that Devin guessed to be about 34-22-35. Bobbi had shapely legs and a very round curvy ass, the kind that Devin liked to fuck whether it belonged to a girl or now a guy.

The three of them got acquainted and enjoyed sharing backgrounds and stories. The topic of sex never came up but Devin sensed that there was something very different about them. Sam mentioned that he and Bobbi were staying in a private rotunda that had a plunge pool. Devin thought that was cool and he was flattered when Sam invited him over to use it the next day. Devin thanked him and accepted the invitation. The three of them called it a night and Devin went back to his room. He was horny but elected not to jack off in the event he got lucky over the next three days.

The next morning after breakfast Devin headed over to the rotunda where Sam and Bobbi were staying. Devin had expected Sam and Bobbi to be in bathing suits when he but that was not the case. Devin entered the rotunda and he saw Sam sitting naked on the side of the plunge pool. Bobbi was no where to be seen. Devin blushed at first and then his eyes instinctively checked out the impressive hunk of meat between Sam's legs. Devin felt his loins stir and his cock twitch as he sat down. Devin noticed that Sam was completely tan with no tan lines and Devin immediately thought about his recent bi-sex experiences. Here he was naked in a private rotunda with a golden bronze god.

"I see that you like to sunbathe in the nude," Devin stammered searching for an ice breaker.

"Oh yeah, Bobbi and I go to nude beaches all the time. We love some of the all-inclusive resorts especially where anything goes," Sam replied.

"Which ones have you been to?" Devin asked.

Devin named at least five different resorts that had notorious reputations for being a swinger's paradise. "Our favorite one is in Jamaica."

"Are you two swingers?" Devin asked already knowing the answer.

"Yeah, we enjoy other people's company if you know what I mean. This place in Jamaica is something else though. There is more fucking and sucking in public then you could imagine. Every night there is an orgy in the nude Jacuzzi," Sam confessed.

Devin looked at Sam's cock and saw that it was standing straight up. It had to be at least eight inches long and more than five inches around. Devin felt his own cock harden under his swim suit as he stared at Sam's cock.

"Oh sorry about that, all this talk got me thinking about sex," Sam said s if he was apologizing for his erection and then he asked, "What about you Devin? What do you do for fun?"

Devin was momentarily lost for words as he didn't want to come right out and admit that he was bi. "Are you into guys? Are you gay?" Devin heard Sam ask.

"Devin, I'm cool with that. If you're gay or bi you can suck my cock if you like," Sam offered.

Speechless, Devin moved his hand toward Sam's big cock and let the back of his hand brush against the stiff shaft. Devin felt like he was in a trance. What was happening to him? He still liked girls but he could not resist a beautiful cock. Devin let his hand close around the thick cock and began to slowly stroke Sam. Devin removed his swim suit and his erect 6" cock popped out. Sam smiled at Devin and then reached for Devin's cock. The two of them stroked each other's cock until Devin had to have Sam's in his mouth. Devin dipped his head and began to suck Devin's beautiful cock. There was no way that Devin could take more than six inches of the thick meat into his mouth but that was enough to satisfy Sam. Devin proved to be a very accomplished cock sucker and Sam just sat back with his eyes closed as Devin worked over Sam's cock. Sam knew Devin would be surprised with the volume of Sam's cum shots. Sam smiled and heaved a satisfied sigh.

Devin then kissed Sam's pecs gently and then kissed a trail down his chest and stomach to Sam's cock. Devin was pleased to find a new experienced young lover like Sam. Sam was relieved when Devin again found Sam's aching cock with his mouth. Devin was gentle yet firm with his sucking, engulfing it and pulling off slowly with long sucks. Devin licked up and down Sam's shaft and balls before resuming sucking off the handsome blonde. Paula and Carla had taught Devin well. It wasn't much longer before Sam trembled and quaked with an astonishing orgasm, being very loud when he cried out with the unintelligible orgasmic cries people make when they cum.

The volume and force of Sam's ejaculation caught Devin by surprise but he kept his mouth on Sam's cock and tried to swallow every delicious drop. Devin licked and sucked Sam dry relishing every drop of cum that Sam's cock spewed forth. When Sam could take no more of Devin's sucking and nibbling, he tugged on Devin's shoulder to bring him up in his arms. The two naked young men cuddled as Devin put his arms around his new lover. Sam and Devin smiled at each other as they jacked on each other's cock. They moaned in delight as their hands worked magic on the other's cock. They were both sporting two stiff boners.

"I would love to fuck you Devin. I have been thinking about fucking you ever since I laid eyes on your hot ass last night," Sam told him.

Devin then got on the pool mat on all fours as Sam prepared Devin's ass to be fucked. Sam squirted an ample amount of lube on his own cock and then knelt close behind Devin. Sam eased his big dick into Devin's well used but tight asshole and Devin uttered an audible gasp. Devin pushed his buns up to meet Sam's penetration and the cock slid in easily. Devin groaned as the thick shaft filled his anal passage. Sam fucked Devin for what seemed to be hours, cumming in Devin's ass twice without removing his cock or going soft. Sam collapsed on top of Devin and Devin was amazed at the young man's stamina. Devin's ass was filled to overflowing with Sam's cum and he felt it ooze from his anus as they embraced. The two of them remained in the same position for several minutes before they separated.

"Devin would like to fuck me now?" Sam asked.

Devin couldn't believe his ears. "Oh yes, I would love to fuck you."

Devin lubed Sam's ass and fucked Sam but he didn't last long and he shot his load quickly into Sam's asshole. Devin stayed in Sam's ass and fucked him until he came a second time. Then Sam fucked Devin and jerked him off. Devin screamed out loud that he was close and Sam jerked him faster. Devin came a third time and cum oozed from his cock covering Sam's hand and dribbling on Devin's pubes. Sam did not cum again but they were both sated for the morning session.

"That was great Devin but I need to get going now. I need to catch up with Bobbi. I hope that we can get together again," Sam said as he stood up and wrapped a towel around his waist.

Devin left the rotunda and made his way back to his room. He showered and then bathed soaking in the tub. He had never expected to get laid so fast at the resort and certainly not by a bisexual hunk. Devin had a late lunch and spent the rest of the afternoon on the beach. That evening he hooked up with Sam and Bobbi after dinner. Sam and Devin took turns dancing with Bobbi and later they called it a night. Devin liked Bobbi and he wondered if he would get to fuck her since she and Sam were swingers. Devin imagined himself fucking Bobbi's ass while Sam fucked his ass, so much for a break from sex.


The next morning Devin returned to the rotunda to find Sam sitting naked by the plunge pool. Devin took of his bathing suit and sat next to Sam. Devin's hand immediately went for Sam's cock. Within seconds Sam was hard and Devin was jerking him off. Sam took a hold of Devin's cock and began to jerk him off as well. The two hot looking guys sat next to each other and stroked each other's cock.

Bobbi came outside completely naked got in the plunge pool and knelt in front of Devin. Bobbi took Devin's stiff cock in her mouth. Devin was shocked and but pleased with her action. Sam pulled Devin's head down on his cock. Bobbi was a very good cocksucker and Devin loved her technique. Devin surprised himself when he came in Bobbi's mouth before Sam came in Devin's mouth. Bobbi sucked every drop from Devin's cock and then she nibbled on the cock head driving him crazy.

Just then Sam shot his wad into Devin's mouth and Devin swallowed quickly to catch every cum shot from Sam's pulsating cock. Bobbi continued to nibble on Devin's cock as it took all of his will power to keep his mouth on Sam's cock. The sensations were almost unbearable and Devin finally gave in and pushed Bobbi's head away. It had been one of the best blow jobs Devin had ever received from anyone. Devin was panting and gasping when the three of them separated.

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