tagTranssexuals & CrossdressersDevin Learns About Trannys 04

Devin Learns About Trannys 04


Devin was sitting in his living room Saturday morning sipping his second cup of coffee when his mind wandered back to last week. He had expected things to slow down a bit after his weekend at the resort particularly since Paula and Carla were in Europe for three weeks. Devin did not plan on any encounters as he did not call Lee but he was also not prepared for his boss's secretary Sondra. He thought briefly about Paula and Carla romping around Europe. Then Devin thought about his boss's secretary Sondra. It started on Thursday evening after the office staff had stopped at their favorite bar for a couple of drinks.

Sondra had joined the staff for a drink and she drank a little too much. Being the junior staff member in the group, Devin was designated to drive her home. On the way home Sondra got amorous and sucked Devin's cock while he was driving. She was an excellent cock sucker and Devin came in her mouth. Sondra swallowed every drop of Devin's cum and then complimented him on his nice cock. Devin dropped Sondra off at her house and then he went home. He had worried all Thursday night about the encounter and how he would face her on Friday.

Sondra was not only the boss's secretary but she was married. Devin had never had sex with a married woman before and it had made him a little nervous. Sondra was 10 years older than Devin but she was attractive with short blonde hair, small tits, shapely legs and a great ass. Sondra wasn't the only older woman that Devin had been with but she was the only married woman. That Friday Devin learned more about Sondra in particular how she loved to take it in the ass.

On Friday Devin was called to his boss's office where he was greeted by Sondra. She led him into the office and then she closed and locked the door. Devin's boss Jim was no where in sight. Devin had been nervous in the presence of Sondra and he thought that she was going to speak to him about Thursday night. Devin recalled that conversation and the events to follow as he stared out his living room window.

"Sondra about last Thursday, I'm sorry that I got carried away. I shouldn't have let you do that," Devin stammered.

Sondra smiled and then spoke, "You silly young man. I loved it. I loved sucking your cock and swallowing your cum. You have a great cock, that's why I called you this morning. I want to suck you again"

Devin was floored, "Here, now, in Jim's office, where's Jim?"

"Jim's out of town silly," Sondra told him and then she dropped to her knees and began to unbuckle Devin's belt.

"Sondra, please don't do that. You're married, this is Jim's office," Devin pleaded.

"Oh stop your fussing. Jim and I do this all the time. A day doesn't go by that Jim doesn't have his cock in my mouth, pussy or ass."

Devin heard her but he still had a difficult time believing her. However he heard her say in her ass and that got his attention. "He fucks you in the ass?"

"Yes, I love it in the ass. Would you like to fuck me in the ass? I bet you would," Sondra replied in a sexy tone.

Then she stood up and went over to Jim's desk. She took some lube and paper towels from Jim's desk. She then leaned over the desk and pulled her skirt up over her back and lowered her panties to her knees. Devin stared at her shapely gorgeous ass and he could not contain himself. He dropped his pants and moved closer to her. She handed him the lube and told him to get her ass ready for his cock. Devin lubed up her ass and his cock. Then he fucked her ass until he came flooding her rectum. Devin was thinking about that encounter when the door bell rang.


Devin was annoyed that the door bell interrupted his thoughts. He checked the time and saw that it was nearly noon. He had lost track of time while deep in thought. Devin answered the door wearing his normal tee and shorts. Standing there was a very pretty blonde girl wearing a very short summer dress. The dress was cut at least 12" above the knee and showed of her gorgeous legs. The girl was carrying a small bag and Devin assumed it contained whatever she was selling.

"Can I help you?" Devin asked politely.

"Devin, it's me, Lee."

"Lee, I didn't recognize you. You look beautiful."

"Can I come in?"

"Yes, of course, come in."

Devin smiled at the beautiful Lee curled up on his sofa. Lee's gorgeous legs were displayed below the short dress.

"Can I get you something to drink?" Devin asked.

"Water would be fine," Lee responded in a soft sexy tone.

"Coming right up," Devin said.

Devin sat next to Lee on the sofa and held his coffee mug up in a toast.

"Cheers!" Devin offered.

"How come you are not working today?" Devin asked.

"The boss's daughter is getting married today so the Bistro is closed for the weekend. So, since I had the day off, I thought I would come by for a visit."

"It's good to see you. You really look like a girl. I would not have recognized you if I passed you on the street. You know that Paula and Carla on vacationing in Europe."

"Yes, I know that. I can only imagine what they are up to with those European men."

Lee licked what he saw in the condo and thought that Devin had good taste in furnishings. Then Lee maneuvered his body around so that he leaned into Devin's body and cuddled up close. Devin instinctively put his arm around Lee and let his hand drop onto Lee's breast. Lee cooed as Devin's hand gently massaged Lee's tits through the dress. Devin felt like he had a woman in his arms and his own cock had hardened in his shorts.

"Your titties are coming along nicely. They are budding like a young girl's," Devin remarked.

Devin let his hand slip inside the dress and find one of Lee's naked breasts. Devin toyed with the tit and the erect nipple as he excited Lee and increased his own arousal. Lee then stood up and let the dress fall from his body. He stood in front of Devin wearing only his panties and Devin could see the erection through the transparent material.

"Hold me Devin," Lee whispered.

Devin stood up and Lee pulled Devin's tee shirt up and over Devin's head. Now Devin just in his shorts took Lee into his arms and they began to hug. Devin loved the feel of Lee's tits against his bare chest and he loved the smooth feeling of Lee's skin. They pressed together holding each other so tight that a ray of light could not have passed between them. Devin let his hands drift down to Lee's panty covered ass and he took both of Lee's ass cheeks in his hands. Their legs rubbed against each other's pubes and both hard cocks were pressed against the other's thigh. Devin slipped his hands inside Lee's panties and gently squeezed the smooth curvy ass cheeks.

Lee lifted his head as a girl would to be kissed and instinctively Devin kissed Lee. It was a tender kiss and Devin had forgotten how soft Lee's lips were. They kissed again and this time Lee's tongue probed Devin's mouth gently forcing it open. Devin returned the French kiss and their tongues dueled with each other as they continued to hold each other. Lee kissed like many of the girls that Devin had dated. Lee broke their embrace and dropped to his knees. Lee pulled Devin's shorts down to his knees allowing Devin's cock to catch in the waistband and then spring free in front of Lee's face.

Lee didn't take the cock in his mouth at first but instead he planted soft kisses up and down Devin's throbbing stiff shaft. Devin moaned as the soft lips kissed his cock and balls. Lee gently stroked the hard cock as he kissed Devin's tight ball sac. Just about the time that Devin thought he would go out of his mind with desire, Lee's mouth covered Devin's cock head and Lee let the cock slowly enter his mouth. Devin was incredibly turned on and then he realized that he was about to cum. Devin held Lee's head and let his fingers run through the soft blonde hair as Lee's head bobbed up and down.

Devin felt the surge in his loins and the pressure in his cock just seconds before he unleashed his load into Lee's mouth. Devin ejaculated into Lee's mouth and Lee swallowed quickly as one jet after the other shot into his mouth. Devin felt his cock pulsate as five or six strong streams of semen ran through it and into Lee's mouth. Then Devin felt the barrage subside as Lee sucked the remaining cum from Devin's cock. Devin felt weak kneed and he held Lee's head firmer as if for balance. Lee continued to suck Devin's softening cock and then Lee nibbled on the sensitive head of Devin's cock causing Devin to shiver and groan. Devin couldn't take the gentle nibbling on his cock as he almost felt faint so he pushed Lee away from him. Reluctantly Lee let Devin's cock slip from his mouth but not before giving the head one more nibble. The sensations rippled through Devin's body as the head of his cock left Lee's mouth with an audible pop.

Devin staggered over to the sofa and flopped down in it as he was completely drained. Lee snuggled up to Devin and caressed Devin's chest. Then Lee kissed Devin again and pushed his tongue into Devin's mouth. Devin subconsciously kissed Lee back without caring that he had just cum in Lee's mouth. Devin was sure that he could taste his own cum in Lee's mouth but he had done that before so it didn't bother him. As Devin continued to recover he and Lee continued to kiss and Devin once again rubbed and fondled Lee's tits.

Devin lowered his head to Lee's breasts and began to kiss and suck them as he had done before. Lee's nipples were rock hard and Devin gently nibbled on them. Devin held one nipple in his teeth as he ran his tongue over the hard nub. Lee cooed as Devin worked on the tits and nipples and Lee leaned back on the sofa. Devin continued his sucking and fondling of Lee's tits and then he decided to jerk Lee off. Devin let his hand trail down Lee's body and inside Lee's panties. Devin took the hard cock in his hand and jerked it slowly. Devin liked holding the stiff dick in his hand.

Lee placed his hands on Devin's head as Devin continued to suck on Lee's tits. Then Devin felt the steady light pressure on his head as Lee pushed down on it. Devin lowered his head and placed kisses all along Lee's firm tummy and as he did he stared at the hard cock in his hand. Lee groaned and pushed some more making it clear what he wanted Devin to do. Devin continued to kiss Lee's firm abs and he made note of how smooth Lee's skin was. Devin stared at the cock in his hand.

"Devin, please suck my clit. My clit is hard and throbbing. Please take my clit in your mouth," Lee pleaded.

Devin lowered his mouth onto the hard cock and pulled Lee's panties down further in the process. Lee groaned as the warm mouth covered his cock. Devin liked the feel of the cock resting on his tongue and as he sucked on the pecker. Devin was lost in his own thoughts when the first stream of cum shot into his mouth. Lee was incredibly turned on and it hadn't taken him long to cum. Devin reacted by swallowing the first stream and then more cum entered his mouth and he swallowed that too. Devin didn't find the taste repulsive at all and it wasn't any worse than drinking down a woman's love juice. Devin had been with some women who were squirters before and he recalled the juice being shot into his mouth. It just didn't seem that different. Lee groaned and moaned as he unloaded in Devin's mouth and then his cock softened quickly.

Devin liked the feel of the worm softening in his mouth and then he teased Lee just as Lee had done to him. Devin nibbled on the cock head and he relished in the way Lee trembled and shivered from the sensations. Lee pushed Devin's head away and Devin let the soft cock slip from his mouth. Then Devin moved up to Lee and French kissed Lee letting Lee taste his own cum. The two of them kissed for quite awhile and Lee was overcome with lust and pleasure. They rested and chatted and then decided to go out for dinner.

"I have a cocktail dress with me," Lee replied.

"That's perfect. Let's get cleaned up and go out for dinner. What would like to eat?"

"Besides you," Lee giggled and then said, "Any type of food is fine but I don't eat beef."

"How about Italian, there is a great little romantic place I know?"

"Italian would be wonderful."

"Great I'll call for reservations and we can get cleaned up and get ready," Devin added.

Devin called for reservations while Lee showered. Then Devin showered as Lee pressed the dress. When they were ready to go Devin looked at Lee and admired the beauty. Lee looked stunning in the cocktail dress and Devin knew that no one would ever be able to tell that Lee was a guy. They left Devin's house and Devin opened the car door for Lee. As Lee got in the car and swung his legs around, Devin once again admired the shapely gams. As Devin drove to the restaurant he stole several glances at Lee as he was enamored with the beautiful gay soon to be tranny seated next to him wearing the short cocktail dress.


Devin arrived at the restaurant and parked in the street about two blocks away. As he and Lee walked down the street arm in arm, Devin felt as if all eyes were on him. Devin was still nervous but had no reason to be because all the guys that looked their way were taken with Lee's beauty. When they entered the restaurant the host greeted them in Italian and showed them to their table. Many a head turned to check Lee out as they were seated and Devin mused at the women who playfully slapped their dates when their eyes roamed. Devin all of a sudden felt very good about being in public with Lee and he was pleased that he was the envy of other men. If they only knew what was beneath the cocktail dress, would they ever be surprised.

Devin and Lee had a delicious meal and some wonderful Italian red wine. They were feeling very romantic given the ambiance of the restaurant and Devin didn't even think of Lee being a guy the entire evening. After dinner they drove back to Devin's house and as they did Lee played with Devin's crotch. Lee rubbed his hand over Devin's crotch and got Devin's cock hard again. Lee teased Devin by rubbing the stiff cock through his pants but he never took Devin's cock out as they drove.

Devin pulled the car into his garage and he and Lee entered the condo and went straight to Devin's bedroom. Once in the bedroom Devin and Lee came into each other's arms and kissed deeply. Devin reached behind Lee to unfasten the top of the cocktail dress but Lee turned his back to Devin who then unhooked the clasp. Devin peeled the dress down Lee's arms and then it slid down Lee's body and fell to the floor. Next Devin unhooked Lee's bra and let that too slide down Lee's arms to the floor. Devin wrapped his arms around lee and cupped Lee's tiny breasts in his hands. Then Devin dropped to his knees and removed Lee's shoes and thigh high hose letting them gather on the floor with the dress and bra. Devin looked at Lee's shapely ass briefly and then he peeled Lee's panties down uncovering the shapely buttocks.

Devin place loving kisses on the cheeks of Lee's ass before he stood back up. Lee turned to face Devin and then proceeded to undress him. Lee removed every article of clothes from Devin's body except Devin's briefs. Then Lee dropped to his knees and slowly pulled the underwear down Devin's legs to his ankles. Lee made sure that Devin's cock got caught in the waistband of the underwear and then sprung out. Lee loved to do that and see a big dick bob in front. Lee then took Devin's cock and gave it a few sucks before standing up again and kissing Devin.

"Take me your bed and make love to me like a woman," Lee whispered.

Devin picked the smaller Lee up and effortlessly carried Lee to the bed. Devin placed Lee on the bed and Lee stretched out and opened his legs exposing his asshole. Devin took the lubricant from his night table and squirted some directly on Lee's anus. Devin then used his finger to lubricate Lee's anal passage. Lee cooed as Devin work his finger in and out of Lee's ass and Devin smiled when Lee's cock got hard. Devin then rocked back on his haunches and applied a liberal amount of lube to his cock. Devin stroked his cock into hardness and then placed the head at the entrance to Lee's asshole. With a gentle steady push Devin's cock entered Lee's ass and then Devin gently rocked back and forth going a little deeper with each movement. Once Devin's cock was fully embedded in Lee's ass, Devin leaned over and began to fuck Lee like a woman.

Lee wrapped his arms around Devin and pulled him in tight so that Devin could feel Lee's firm nipples against his chest. Lee also wrapped his legs around Devin's torso and humped up at him as Devin pummeled Lee's ass. Devin could feel Lee's hard cock pressing against his abdomen each time that Devin pushed in deeper. Lee was groaning and crying out for Devin to fuck him. Devin felt his balls overheating so he picked up the pace as he looked forward to filling Lee's ass with another load. Lee stiffened underneath Devin's body and then Devin felt the wetness on his abdomen signaling him that Lee had ejaculated between their bodies. Devin was so close that he thrust all the way in and let loose in Lee's ass. Devin fired a barrage of cum deep into Lee's bowels and he held still as his cock pulsated with his ejaculation.

The two of them were spent and they remained still for several minutes in each other's arms. Lee then kissed Devin and Devin kissed him back and they cuddled a little while longer before Devin rolled off to the side. Lee rolled to his side and Devin snuggled up behind him. Devin drape one arm over Lee's body and his hand came to rest on Lee's breast. Devin's semi-hard cock nestled in between the cheeks of Lee's ass and they fell asleep in that position. They were both sexually sated and they slept soundly through the night. Lee had never asked to stay the night. It was just assumed that he would.


Devin woke up Sunday morning in bed alone. Then he heard lee in the bathroom and he was pleased that Lee had not left. Devin lay in bed and recalled the events of the weekend and the things that he had done. Sure Lee didn't have a pussy but Devin liked fucking ass better than pussy. Lee gave great head and his body was incredible. Lee had the body of a beautiful young woman with cute titties and an ass that wouldn't quit. Devin was stroking his hard cock when Lee came out of the bathroom.

"Thinking about me?" Lee said when he saw Devin's cock.

"You know I am," Devin replied.

Lee got back in bed and immediately lowered his mouth to Devin's cock. Devin sighed as Lee's warm wet talented mouth covered his cock. Lee then got on his side with his head toward Devin's feet and took Devin's cock back in his mouth. Devin looked over at Lee's body and saw that Lee's cock was erect so Devin rolled to his side and took Lee's cock in his mouth. The two new found lovers sucked each other's cock until they both ejaculated in each other's mouth. Devin released Lee's cock after it softened in his mouth but Lee went right on sucking Devin's cock keeping it hard.

Devin fondled Lee's ass and probed Lee's anus. Devin discovered that Lee's ass was already lubricated in anticipation of the morning fuck. Devin positioned Lee on all fours with his ass raised in the air and his head on the bed turned to one side. It was Devin's favorite position for Lee and Devin played with Lee's ass for several minutes before he fucked it again. It seemed like an hour before Devin came again but he didn't mind as he loved watching his cock slide in and out of Lee's shapely ass. Devin ran his hands along Lee's hips and buttocks as he fucked him. By the time Devin ejaculated another load into Lee's ass they were both tired and achy from holding the doggy style position for so long. Both of their thighs were burning so Devin recommended a hot bath.

Devin got out of bed and ran the water in his oversized tub adding bath oil beads. Then Devin made the coffee as the tub was filling with the hot oily water. Devin returned with two cups of coffee and set them down near the tub. Devin then went to get Lee who was resting face down on Devin's bed. Devin looked at Lee's hot ass and once again he felt that sensation in his loins. "God I am becoming insatiable," Devin thought to himself.

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