tagTranssexuals & CrossdressersTaste of True Friendship Ch. 08

Taste of True Friendship Ch. 08


Dan's first day at college was a shocker. As with all freshmen, he was required to live in a dorm for his first year, or at a fraternity. He wasn't big on the Frat idea so he took the luck of the draw on a dorm room. He was assigned to 3C on the top floor of the building and away from the stairs and elevator, not a bad location really. But finding the building and finding the room itself was a frenzy- -new kids all over the place lugging their belongings around trying get situated for the start of the school year. But he finally got to his room with his paucity of belongings. He traveled light: a duffel bag stuffed with clothes, his violin, and a suitcase with his miscellaneous items, art supplies, laptop computer, toiletries, and so forth. He figured what he hadn't taken with him he would ask his mother to send to him or just buy what he needed at school.

It was when he walked into Room 3C, however, that he got the shock. Seated on one of the beds was a boy, stark naked, with his legs spread apart, and between those legs was another boy also stark naked, kneeling, going down on the sitting boy. Dan just stood there with his mouth open but the fellow sitting on the bed acknowledged Dan's presence and with a wave of the hand directed Dan to the other bed on the opposite side of the room. Dan walked over and deposited his belongings on the bed and turned to witness the merry scene taking place behind him.

The kneeling boy was sucking the other boy's cock with unbridled enthusiasm. His head was bobbing up and down and his naked fanny was undulating in phase with his head. Up and down, up and down, up and down. The guy was like a machine. This activity went on for several minutes during which the sitting boy leaned back on his arms with a look of pleasure on his face and Dan just stood there mouth agape. Finally, the kneeling-boy stopped bobbing his head and held it very still, pressed down onto the organ of the sitting-boy. There was a "MMMMMMMmmmmmmmMMMMMMM" sound from sitting-boy and a gag/gurgle sound from kneeling-boy as sitting-boy achieved his orgasm. Once that part was over, kneeling-boy got up, grabbed his clothes off sitting-boy's bed, quickly dressed (Dan couldn't but help seeing kneeling-boys semi-erect, rather large cock as he did this), and left the room without saying a word. Sitting-boy laid back on his bed with a look of satisfaction on his face.

"Hey, you're my new roomie! You've got to be....Dan? Right? I wasn't' expecting you until later this afternoon." Sitting-boy, now laying-boy, was in high spirits. He pointed to the now closed door to the room and said, "Hey, don't worry about him. He's just my old roomie from last year back for a visit."

The look on Dan's face, a combination of shock, disbelief, and curiosity registered with sitting-laying-boy.

"Dude, don't worry about that. He just likes to suck my cock and...well....I just couldn't help but let him, you know?" He laughed lustily. "I know what you're thinking. No, it's not a requirement to do that to room with me."

"I'm relieved." Dan said evenly, trying not to betray his unsteadiness. "Well, I'm Dan. But it looks like you know that already."

"Yeah, I do. I got the word the other day. By the way, my name is Peter." He stuck out his hand from his reclined position.

Dan reached out and shook it firmly and said, "That's an apt name, if you ask me."

Peter laughed again, that licentious laugh, "That's a good one, Dan. Not like I haven't heard it before. But I like it anyway."

Peter got up off the bed, slipped into his sweats, and started to give Dan some help getting situated. The room was small but laid out to give it as much space as two people needed. There were two beds in the room, two stand alone armoires against the wall at the foot of the bed, and two low dresser/desks beside the beds. There were lockable drawers, one in the armoire and one in the dresser/desk. Peter had put up a bookshelf over his bed but there was none over Dan's bed. The wall between the beds was mostly a large window and the space underneath the window accommodated a small table with two chairs.

"Dan, I hate to tell you this but, right out of the gate I think you need to understand: I 'entertain' a lot in this room." Peter took on a proprietary air. "I hope it won't be too much of an inconvenience for you but, inconvenience or not, I'm going to do it anyway. There's always the lounge downstairs, or the student union, or the library to use if you can't handle the traffic. Sorry."

Somehow Dan didn't believe that Peter was all that "sorry" but it did seem like he had squatting rights. "O.K., Peter, I will find a way to work around that."

Little did Dan know that Peter would present more of a problem that he thought.

Peter was a junior the college. He still lived in the dorm because he was Persona-non-grata to the fraternities. Something to do with setting off smoke bombs during pledge week that caused a bunch of pledges to head for the emergency room. The school didn't nail him for it but the frats all knew who did it and black-balled him. Peter didn't care. He was a happy-go-lucky guy, cutting a swath through college life, and absolutely enjoying himself. He was a Economics major whose plan was to parlay that knowledge into a mega-bucks career. He was lively, fun, and had a great way with the women (and some of the guys, too). He also got laid more than three people, from what Dan could tell.

Dan launched into his studies. In addition to his "solids" he added art and design classes to his curriculum. He was busy with studies but he couldn't help but yearn for some "solid" sex, considering he had a fairly steady diet with Tatiana before he left for school.

Peter was more than happy to help. He introduced Dan to lots of girls. Most of them, though, were exactly the type that Dan had no interest in, the flighty, ditzy, self-absorbed ones. Peter had a lot of success sport-fucking with them but Dan wasn't just interested in sex- -he actually thought that having some sort of intellectual relationship was important. One or two of the girls were bright enough to attract him but the sex was not satisfying. He did have his share of orgasms (both from playing with the girls and from playing with himself) but there was something missing. One girl in particular, a sophomore psychology student, would give Dan a blow job at the drop of his pants but somehow his climax left him wanting more. Another played hard to get with Dan and, when he persisted in his lack of interest, she finally went to bed with him. It was straight sex, nothing spectacular. Dan didn't return for more. She thought Dan was gay.

Now, Peter, as Dan had already seen, was pretty much "omni-sexual"- - if it had to do with sex, Peter was "up" for it- -so Peter introduced Dan to some friends who were either gay or bi-sexual. Dan didn't fancy the gay boys, they were just like the ditzy girls- -too flighty. His encounters with the bi-sexual boys were better because they were more masculine but they made no bones about liking sex with men as well as women. It was with one of these bi-sexuals that Dan had his first experience with anal sex.

Remember, Tatiana hadn't been into anal sex herself but had played with Dan's asshole on occasion. But she had never really done any penis sized penetration with Dan- -no dildos, no cock sized objects. So, when Dan was confronted with a guy who wanted to have his ass fucked, Dan indulged him just for the novelty. This guy, Chad, was a sophomore who had his own apartment off campus. That made the escapade easier, not having to worry about some dorm mate barging in on them.

The purpose of Dan's presence with Chad in his apartment was understood so, without much by way of preliminaries, Dan and Chad wound up on bed naked. Chad "assumed the position" on his knees and was stroking his cock when he handed Dan a condom said, "O.K. do it to me." So much for any "relationship".

Dan stroked his own cock into hardness, slipped on the condom, held Chad's butt cheeks in both hands, and poised his cock at the entry to Chad's anus. "C'mon, DO IT!" Chad was frantic.

Dan plunged his penis into Chad's ass. He wasn't gentle about it; he used one quick thrust. He met some resistance from Chad's sphincter but, it was apparent that Chad had done this more than once, his asshole was fairly relaxed. Still, after Dan had his cock into Chad, his asshole tightened snugly around Dan's hard cock. Dan pumped in and out, in and out.....He was surprised how smoothly his cock went in and out...He could only imagine that Chad and "pre-lubed" to make it easier. Chad continued to stroke his cock as Dan ass-fucked him and, from the sounds that Chad was making, he was thoroughly enjoying the experience. For his part, Dan felt good but not ecstatically excited.

"Let me know when you're going to cum, dude." Chad grunted.

But Dan wasn't any where near shooting his load- -he just wasn't that turned on. He kept pumping Chad's ass with vigor.

Finally, Dan said, "Sorry, buddy. I'm just not getting there."

A moment later, Chad jacked himself into an orgasm. His semen spouted out of his dick all over the sheets on the bed. It was a copious amount of cum, more than Dan had ever seen from himself.

"O.K., dude, you can pull out now." Chad said breathlessly.

Dan complied. His dick was still hard and covered with the condom. Fucking Chad's ass hadn't made him come but he knew that he needed to, he had too much cum worked up inside him. Dan just knelt there with his dick sticking out.

"You didn't come yet?" Chad was astounded. "Dude, you need some help!"

With that, Chad reached out and slipped the condom off of Dan's penis, tossed the limp latex membrane onto the floor, and pushed Dan over onto his back. Then Chad proceeded to go down on Dan's cock. He took it deep into his mouth, all of the way to his throat. Then he pulled his mouth back so he could lick the shiny head and jacked away on Dan's shaft as he sucked. His hand was slippery from his own saliva on Dan's shaft and that made stroking Dan's cock more comfortable. Dan closed his eyes and savored the sensation. It didn't take but a minute more for Dan to shoot his wad. It all went into Chad's mouth and Chad swallowed it, every drop- -not a bit escaped his lips. Chad kept his mouth on Dan's cock until it went flaccid again.

"Dude! "That was a load and a half!" Chad seemed impressed as he licked his lips. "You needed to come, big time!"

"Yeah, I guess I did." Chad answered without enthusiasm. "I guess I did."

Leaving Chad on the bed to clean up his own jizz on the sheets, Dan got up, put his clothes on, and left almost forgetting to thank Chad for his hospitality. Dan had gotten off but real sexual satisfaction was eluding him.

^ ^ ^ ^^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^

Dan met Dana in his second semester in his "Introduction to Advanced Design" class. She was tall and willowy brunette. Dan was 5'10"; Dana was 5'9". Dan was going on 20 and still a freshman and Dana was 23 and a junior. They pretty much saw eye to eye, literally, intellectually and (as Dan was to find out) sexually. She had long dancer's legs, narrow hips, a trim waist, but had a gorgeous looking chest. Her face was pretty, not drop-dead gorgeous by any stretch, but pretty with big eyes, a thin nose, and full lips- -her complexion was creamy white. Dan was stunned the first time he saw her, and he wasn't easily stunned. In a lot of respects she wasn't much better looking than a lot of the other girls on campus but she had a manner about her that was, in a word, attractive. Dana was calm but enthusiastic, intelligent but not pedantic, serious but quick to laugh, a leader but not domineering. Dan was smitten.

They began to date- -actually, formally date- -dinners and movies, trips to the museums, attending concerts, everything but meeting the parents. They took the time to find out about each other, their backgrounds, their likes and their dislikes, their interests. It turns out that both were interested in music and art- -and, of course, design. They made a good couple- -their names even matched.

They didn't get "intimate" for many weeks. There was some kissing and petting but no sex of any sort. Dan had to satisfy himself by masturbating; he didn't want to play the field while he was seeing Dana.

Inevitably, though, it came time to have sex. Dan was nervous as he sat on her couch with her but he knew that sex was going to take place that night- -he just knew it.

And he was right.

There was the obligatory preliminary kissing and petting but it was clear that passions were on the rise. Dan's hands roamed to Dana's breasts and massaged them through her blouse and bra. She had firm, full breasts with tiny nipples that he could feel becoming erect through the material of her clothes. He summoned up all of his experience and gently began to tease and tweak them while plying Dana's lips with his kisses, the kind where his tongue and her tongue were alternately in each other's mouths. He could feel him self getting very hot and his cock becoming very hard.

Dana disengaged, slipped off the couch to her knees, and unbuckled Dan's pants. She unbuttoned them and unzipped his fly seemingly with one motion. His cock leaped through the opening in the front of his boxers fully erect. Dana had that effect on him. Dana proceeded to give Dan a millennium class blow job. It's not like Dan hadn't had his cock sucked before- -by men and women- -but this experience was in an entirely different category. How different could one blow job be from another? After all, the mechanics were pretty much the same from one to another. But this seemed to be an experience that he had never had before. Her hands were firm around his shaft, her lips were soft, and her mouth was warm- -warmer than he remembered ever having experienced before. His cock filled her mouth but she didn't seem to strain at all getting it all of the way in- -her nose was up against the fabric of his boxers pressing on his stomach. She massaged, and stroked, and sucked, and tongued, and twisted her head to get a better angle on his penis, and pressed her body as close to his as she could as she did these things.

She took a long time. She sped up and slowed down and rested. Her rhythm was regular but, to use a musical term, sometime syncopated. Her throat pulsed as she hummed to send vibrations into his phallus. That resonated all of the way into Dan's abdomen. At long last, Dan could feel himself beginning to come. He shot once into her mouth, and then she pulled back and let his semen shoot onto her face and lips and all over her hand which was still gripping his shaft. She swallowed what was in her mouth, licked her lips, and then licked both her hand and Dan's cock to clean up the semen there. She used the palm of her hand to wipe the rest of Dan's cum from her face and then licked her hand and fingers clean. With a smile, she stood up, leaned over, and gave Dan a kiss on the lips sliding her tongue between them. Dan could taste his own semen on her tongue and on her lips. He dick got stiff once more and he felt like he was just about ready to come again.

Dan moved to pull Dana back down on the couch. His intention was to lay her down, strip her clothes off of her, and fuck her brains out. This didn't happen.

She resisted Dan's move and patted him on the face. "I think that's enough for right now, Dan my dear." Her tone was affirmative and made Dan not want to try to contradict her. Who knows? Maybe she was having her period and didn't want to talk about it. Besides, they would have more time to work on that.

Over the next couple of weeks whenever Dan and Dana got together, this scenario repeated itself almost without variation. Dan was certainly achieving satisfaction but felt a little helpless that Dana wouldn't let him have regular sex with her.

That day was coming, too.

They were on the couch again, beginning to initiate the making-out/blow-job sequence when Dana spoke up, "Dan, I'd like you to do something for me. Indulge me a little."

Dana's request was serious but not ominous. "It is a little fantasy that I've had."

By this time, Dan was pretty much ready to do anything that would break out of their routine sex play. Plus, he thought this might actually lead to his being able to properly fuck Dana.

"Yes, Dana. If I can." Dan's answer was mild and compliant.

"Come here with me." Dana led him by the hand from the couch to the bedroom.

(Dan thought, "Things are looking up!")

"Dan, you are such a beautiful man! Did you know that?" Dana was being flattering and seductive both. "You have such wonderful features, smooth skin, lithe manner. Let me do something."

She didn't wait for answer but began to unclothe Dan. She did it slowly and sensuously, teasing his shirt over his head massaging his chest while she was doing it; undoing his pants and pulling them down over his hips and down his legs; removing his shoes and socks while caressing his ankles and feet. Dan enjoyed the sensation and his dick did too for it became almost immediately erect once his pants and underwear were off.

Dana sat Dan down on a small chair that was in front of her dresser. She opened a drawer, reached inside, and pulled out a make-up kit. Dan began to feel a little twitchy but was good to his word let her indulge her fantasy.

Dana made up Dan's face- -the whole nine yards: foundation, blush, eye liner, mascara, eyebrow pencil, and lipstick. Dan's Asian heritage left him without much facial hair- -hardly any at all and so the make-up went on easily and looked wonderful once it was on. Also, Dan's hair was long, down to his collar; she didn't need to put a wig on him to complete the look. But as it was, he was transformed from a good looking youthful boy to a very sexy looking woman. He was astounded as he looked in the mirror; Dana was pleased.

"Now the rest!" Dana said as she brought out some woman's clothes from the closet. They were her clothes but her size and Dan's size weren't that much different. Her clothes should fit Dan- -and they did. She picked out a floral dress, a padded bra, panties, and leather thongs. Once they were on, the project was complete. Dan, much to his surprise and much to Dana's glee, looked for all the world like "She".

"O.K., now. Let's go out!" Dana was eager to display Dan to the world with his new look.

They drove down to the local shopping mall and (what else?) shopped. Dana chatted with Dan as if he were one of her girlfriends. It was only slightly different than the way they usually conversed. She was a little more particular in her observations about this person or that person, this outfit or that outfit etc. Dan found that he didn't mind this as that was the way his mind usually worked too, but he rarely had an opportunity to talk that way with the people he was with. He remembered that he and Tatiana would have conversations like that but certainly not with anyone else, especially the guys he hung around with.

The experience was delightfully freeing for Dan. He enjoyed seeing himself in feminine clothes and he felt good wearing them- -natural. He felt like he could relax and not have to keep up any sort of masculine posture. And it answered a question that had been in the back of his mind, unexpressed but there nevertheless. He wondered why he always felt a little out of place wearing men's clothes. He swayed his hips as he walked, used his hands when he talked, and generally acted like a girl. It was delicious.

Dana was enjoying it too. It wasn't just because it was her achievement but she was thrilled that Dan was enjoying himself. Her mind ran with the possibilities.

When they returned to Dana's apartment from their outing, they fell into bed together fully clothed. They began their love making by undressing each other. First, Dana removed Dan's garments and then Dan began to work on Dana's.

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