Taste of True Friendship Ch. 09byBenny_Blank©
Dan and Dana kept up appearances in public. Dana was thoroughly accustomed to womanhood and had absolutely no difficulty continuing in that role. Dan, on the other hand, was new to his cross-dressing life. He maintained his straight male persona during school days and when he was in the dorm but, when he was with Dana at her place, he made it a habit of dressing up. It wasn't just wearing girls clothes. He fixed his face, coifed his hair, polished his toenails, and made sure his legs and face were hairless. But he did not do his finger nails as those would have been to conspicuous in public and it was too much of a pain in the ass to do each time he was at Dana's just to have to remove the polish the next morning.
Dan finally began to feel comfortable with himself. All the years growing up he had a nagging feeling that he just didn't quite fit in. He wasn't entirely uncomfortable being a boy he just didn't like "boy" things. Testosterone driven activities left him cold. He coldn't tolerate guys "out-macho'ing" each other, he wasn't a sports fan, he didn't like going out and carousing with "the guys", the concept of "sport-fucking" seemed repulsive. He did, however, enjoy womens' things: fashion, art, music, and conversation. He didn't cotton to frivolous, air-headed girls but he did respect and feel comfortable with women who had substance of character.
He discovered that "sex for the sake of sex" wasn't his credo. He had sex with women and sex with men; he had sex with straight women, homosexual men, and bi-sexual men, and- -if you counted Tatiana in her latest stage- -a bi-sexual woman. He had auto-sex, genital sex, oral sex, and (giving only) anal sex. And now he had sex with a transsexual man. Frankly, his latest experience was the most satisfying. Why was that?
As has already been stated, he really didn't like conventional sex with girls, mainly because girls were...well....girls, mostly air-headed and ditzy. He had enjoyed sex with Tatiana because she wasn't your conventional female and because sex with her was, to be sure, unconventional. Tatiana had a way of pleasing him and their experimentation added to his fund of experience. Their brush with digital anal sex and masturbation helped with his fantasy sex life. Plus, Tatiana had taught Dan how to sustain an erection and how to go down on her; both things pleasured her and would pleasure other women too. Dan relished their time together. But for everything there is a season.
Even though other people may have thought so, he didn't see himself as gay and sex with gay men didn't do much for him, other than allow him to give him relief from semen build-up. Besides, flaming gay guys were too flamboyant for him and too much like ditzy girls. Sure, there were gay men who were reserved and intellectual but there was still something about being exclusively gay that blunted sexual passion in him. He had often fantasized about having sex with a straight man but the "macho" factor interfered. If only there were some middle ground, a man who was like a woman. Well? That pretty much described Dana, didn't it?
So, He and Dana fell into a relationship of understanding, affection, and sex. Dana, herself having had transition from living as a man to living as a woman, help Dan with innumerable details involved in his change. Dana told him how she began to question her sexual identity in high-school and took steps to create a new life for her almost immediately after. With her, this entailed counseling while she began to dress and live as a female, medical supervision as she took hormones to soften her appearance and voice, and ultimately plastic surgery for her breast implants. She has opted not to have her penis and testicles removed- -that was a little too drastic for her- -but, other than that, she felt of herself completely as a woman. Oddly, though, Dana told Dan that she enjoyed sex with women as well as men but it was on a different footing participating in it as a woman- - a transsexual woman.
Dan learned quickly. His wardrobe expanded with Dana's help and he became more and more comfortable in indulging in his female mannerisms with her coaching. When they went out together as women, they didn't stay near the college. Their excursions were to other parts of the city or to the suburbs. Dan found that people didn't see them as unusual, just a couple of statuesque females out together doing whatever there was to do: dining, shopping, movies, etc. Neither had the urge to flirt but They frequently got hit on by guys. They played off of these advances as most girls would, they made it clear that they weren't interested. To Dan, though, it felt especially wicked putting some guy off; it gave him a sense of independence- -and power.
They loved experimenting with their sex life. After that first session in bed that culminated in Dan giving Dana a blow job, Dan learned that reciprocation was possible. Mutual cock sucking was extremely pleasurable. On occasion, Dana expressed a predilection for anal sex which Dan could fulfill without qualm, owing to his previous experience with Chad. One night, though, Dana broached the subject of anal sex with Dan, I.e., Dan being the recipient of her organ up his ass.
"Dan, Darling. You know there's something we haven't tried yet." Dana was not at all pushy, just affirmative. "You've had anal sex with me but not the other way around. Would you like to try?"
Dan wondered when this subject would come up. He didn't dread it but he was curious as to how they would go about it.
"Dana, I suppose we should. After all, we have shared lots of things together. Why not that?" Dan was trying not to be reluctant but, to be honest, he had to add, "But I've never really had that done to me before. I'm not sure what to expect."
Dan did remember his little session with Tatiana but rightly guessed there was a big difference between having Tatiana's finger tip in his ass versus Dana's entire cock.
"My Dear, you have nothing to fear. I will make it as pleasurable as I can." Dana said in a seductive voice. "First, though, we have to get naked!" The latter she said with enthusiasm and excitement.
It didn't take long for both of them to shed their clothes and hop onto the bed. Dana asked Dan to lie on his back and to let her take the lead. Dan trusted Dana by now and was completely willing to put himself in her hands.
Dana began by massaging Dan's body from foot to neck and back again. Her hands were firm as she kneaded Dan's muscles in his calves, thighs, and abdomen. She took care not to stroke his penis, which was almost a tease to Dan. But as she began to work on Dan's chest, shoulders and arms, Dan could feel his cock starting to become erect. Dana reached off of the bed into her nightstand and came up with a bottle of lotion and began to apply it to Dan's body in the same manner as her initial massage. The lotion was faintly aromatic, not strongly perfumed at all; it went on cold but warmed a bit as Dana worked it into his skin. Once Dana had completed her lotioning on Dan's front, she asked him to roll over on his stomach. As before, she smoothed the lotion onto the back of Dan's legs, his buttocks, his back and his shoulders and worked it with firm massage.
Dana applied an extra amount off lotion onto Dan's buttocks and rubbed it in with both hands in large circles which gradually became smaller and smaller until she was concentrating on his butt cheeks near the crack in his ass. She squirted a couple of dollops right into his crack and began using her fingers to make sure it was getting all the way down inside.
Dan felt the sensation of fingers probing the crack in his ass and flirting with his asshole. It tickled some but was exciting too. Then he felt a single finger press firmly against his anus and begin to insert itself. His sphincter tightened and he heard Dana suggest to him that he relax and let it happen. He did his best. Before long, the lotioned finger was all of the way into his ass. Dana held it there for a minute and then withdrew it almost all of the way. Dan felt another squirt of lotion right on his asshole this time and then felt Dana's begin to move in and out slowly and gently. It didn't take him long to get used to his and he relaxed some more trying to enjoy the feeling.
Dana withdrew her finger all of the way, administered another squirt of lotion, and then began to ply Dan's ass with two fingers. They slid in more easily that her initial single digit probe and, before long, Dan was experiencing a two finger ass fuck albeit very slow and very gentle.
Dana leaned forward and whispered in Dan's ear, "Dan, Dear. You're doing fine. Stay relaxed, O.K.?"
Dan nodded his head and then felt Dana remove her fingers. He felt Dana move around on the bed and then felt her hands on the back of his legs as she gently but firmly nudged his legs apart. Then there was the pressure of her body against him and he became aware of her penis probing his ass just as she had done with her fingers.
She WAS gentle. The entry of her cock into his ass was smooth and gradual but before he knew it he could feel that it was all of the way inside him. It gave him a full feeling as if he were ready for a bowel movement but not as urgent and far more pleasurable. Dana began to pump her dick slowly in and out of his ass using her arms on either side of his body for support, In and out- -slowly- -in and out- -a little deeper- -in and out- -with a little more force. The action of her prick against his anus sent waves of pleasure up through his bowels and he could feel it rub against his prostate which caused his own prick to stiffen. Dana moved her hands so they were under the front of Dan's hips and pulled him up to where he was in a kneeling position. With this, Dan really felt the size and motion of Dana's cock in him. He began to rock back and forth in opposition to Dana's thrusts. The real fucking had begun.
Dan had never felt anything like this before. It was sweetly painful but the sensations all turned into pleasure the more Dana fucked him. He stepped up his cadence and so did Dana. He could feel the force of Dana's body ramming her cock into him, the pounding of her abdomen against the cheeks of his ass, and her scrotum slapping against the back of his scrotum. It felt like his prostate was being squeezed, again and again, which combined with the other sensations to create waves pleasure into his abdomen, his cock and- -in fact- -throughout his body. He was beginning to think he couldn't take much more of it when Dana re-doubled her efforts. That put him to the edge of rapture.
He felt Dana's cock swell inside of him and was aware of warm liquid shooting inside of him. It made Dana's cock slippery and allowed it to move in and out more easily and more quickly. Dana fucked away even faster. Dan knew he was going to pass out any minute.
And then, abruptly, Dana pulled her prick out of his ass all at once. It just slid right out. After having it in there for so long plunging in and out, its removal was almost a shock but one which had a pleasure all of its own. No sooner than he felt Dana's cock was out, Dan knew he was going to come. He moaned and reached in front of him with his right hand and began to jack away at his own dick. Dana quickly slid over onto her back, thrust her head between his legs, under his balls, and gripped his thighs with both hands. She forced Dan's hips down so that his cock as right against her lips. As she opened her mouth, Dan unloaded on her. His warm semen shot from his dick right into her mouth and onto her face. It sprayed so much it ran down her cheeks and onto the sheets. Dana pulled Dan closer to her and made sure that the head of his cock was in her mouth for the follow-up ejaculations. She didn't miss a drop of those. Dan finally stopped shooting and held himself there for a moment savoring the relief of his climax and then, with a sigh, rolled over onto his back.
He looked down at Dana who was still on her back using her hand to spread the cum from her cheeks onto her lips and lick it into her mouth. She made "yummy" sounds as did this and took care that she didn't lose much of Dan's jizz. Once she had done the best she could, Dana scooted up to where she was lying next to Dan. She rolled onto her side, put her arm across Dan's chest and said,
"Darling Dan, how was that for your first time? Good?" She literally purred that sentence.
"Dana...Dana...Dana....I had NO idea it would be like that. It was wonderful." Dan said in exhaustion. "YOU were wonderful!"
Well, that pretty much broke the last sexual barrier for Dan- -or so he thought. At least it did between him and Dana.
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Peter was beginning to be a problem. Dan and he had pretty much gotten along O.K., other than Peter's having incessant visits from his sex pals. It got so Dan could hardly inhabit the room with Peter. It was this girl or that girl, occasionally this guy and that guy, coming- -no pun intended- -by for a romp. Peter wasn't bashful at all about his escapades. Just like the first day Dan had met him, Peter wasn't shy about having sex with Dan in the room. A couple of times Dan tried to be accommodating and work while Peter was getting his cock sucked but regular sex created much more of a disturbance so Dan had to leave the room. They tried putting up a clothesline in the middle of the room and draping it with bedspreads to create some privacy but that didn't really solve the problem.
It's not that Peter wasn't helpful to Dan. Peter did, after all, fix Dan up with more than a few dates. But the constant traffic was pushing Dan to distraction. On top of that, Peter began to tease Dan about his long hair and even spotted Dan's polished toenails and was giving him grief about that. But the last straw is when Peter began sniffing around Dana.
Peter and Dana had classes in the same building on campus. Dana was in advanced art and design and Peter was taking a "dumbbell" art appreciation course just to complete requirements. But Peter did have an eye for beauty and, not surprisingly, spotted Dana who was most certainly beautiful.
Peter was a smooth talker. He chatted her up, tried to get her to go to coffee, made sure he "bumped into her" when they were in the same vicinity, and generally made a nuisance of himself. It got worse when Peter discovered that Dan knew Dana and, in fact, had been dating her. Peter pestered Dan about Dana: What were her likes? Dislikes? Had Dan been "getting any"? and so forth. Dan played off of this and merely said that it was none of Peter's business. But Peter kept pressing. He played the "all I have done for you" card and tried to coerce Dan into giving him a shot at Dana too. Dan was getting exasperated.
One day, Dan found the solution. Had asked to borrow Peter's laptop computer because his was acting up and needed a major clean-up and re-install of programs. Peter was O.K. with that. He trusted Dan. Plus, his personal files were password protected so he wasn't worried about those being broken into. He didn't allow for Dan's intelligence. Dan divined Peter's password (can you imagine Peter not having a password like "fellatio"?) and browsed through some files. He found what he needed.
Dana had been complaining to Dan about Peter. She knew Peter was Dan's dorm mate and thought Dan should be able to deflect Peter's effort on her behalf. Dan explained to Dana that Peter wasn't very "deflectable" when it came to chasing pussy. He got a lot of it and wanted more. He really was a "sport fucker".
But once Dan got what he needed from Peter's computer, he put a plan into action.
"Dana, I think I have a way to cure Mr. Peter's obsession with you." Dan sounded conspiratorial. "What I'd like you to do is to give him the real 'come-on'. He'll ask you to come up to the dorm room. Accept it. Just make sure you tell me when. O.K."
Dana agreed and a couple of days later she told Dan that she and Peter were going to "get together" at 3:00 PM in the dorm.
"O.K. Dana. Now you know he's going to put the make on you right out of the box." Dan was sure this would be the scenario. "So, go along with him just enough to have him get you sitting on the bed. I'm guessing that'll take about five minutes. Then I'll walk in and take over. O.K.?"
Two days later, Dan waited on the ground floor of the dorm while Dana went up to 3C. He gave himself five minutes and then followed her up to the room. He opened the door and found that his calculations were correct. Dana was sitting on Peter's bed with Peter sitting next to her trying to get in a little smooching.
"Peter! Hold on there, Peter!" Dan said as he abruptly entered the room. "I can't believe you're trying to put the make on my girlfriend!"
"Hey, Dude! All's fair in love and war, as they say." Peter was his usual smart-aleck self. "You wanna watch? Like before?" Peter laughed his licentious laugh.
"No, Peter. I don't want to 'watch'. But I'd like to participate." Dan was assertive which took Peter aback. "Let's do a little 'threesome'. How about it, Peter?"
"No way, buddy! You go find your own." Peter was incensed.
"Peter, I think we ARE going to have a threesome. Here's the deal." Dan sat down on the chair, reached into his pocket, and produced a piece of paper, and handed it to Peter.
As Peter unfolded it, he saw that it was a copy of an e-mail, one that he had written to his brother a couple of years ago. He knew right away that this was going to be trouble.
"O.K., Peter. This is how it's going to be. And if you don't follow along, I'm going to make sure that e-mail gets into the hands of the college administration and into the hands of the local police. Understand?"
Peter abjectly nodded his head.
Dan instructed Peter to get naked- -totally naked- -and get down on his knees in front of Dana. Then he told Dana to take her clothes off and sit down on the bed. Both of them complied. It wasn't until the last piece of Dana's clothing was removed that Peter realized that Dana was different- -she had a cock! Dan disrobed also.
"O.K. Peter. You're going to go down on Dana's dick. Right now." Peter began to command Peter.
Peter seemed to hesitate but Dan waved the copy of the e-mail at him and that was the decider for Peter. He leaned forward, grasped Dana's prick and began to massage it into hardness. He lowered his head and took Dana's cock into his mouth and began to suck away.
"Peter! On all fours!" Dan barked out this order and Peter complied. He put his hands on the floor while he continued to suck on Dana's now totally erect penis.
While this was going on, Dan had begun to stroke his penis to get it hard. Having finally achieved that, he knelt down behind Peter, spread Peter's butt cheeks, and spit on his hand, rubbed his hard cock, and unceremoniously rammed his cock into Peter's ass. There was some resistance but it went all of the way inside as Dan drove it forward. Peter emitted a loud grunt as Dan's stiff dick penetrated him. It didn't sound like an expression of pleasure. Dan began to pump away on Peter's ass which got only marginally easier as he continued. Peter's grunts were in rhythm with Dan's thrusting.
"Keep sucking on that dick, Peter! Don't stop!" Dan's orders were firm and sharp.
Peter kept gulping away on Dana's cock, the slurping sounds interspersed with his grunting.
Dan looked up and saw Dana's face. She had a look of wonderment and pleasure. Dan winked and smiled. "Baby, this is fun isn't it" He saw Dana blow him a kiss.
"Take your mouth of off her cock, Peter! Look back at me!" Dan snapped.
Peter interrupted his cock sucking and did what he was told. When he turned to look at Dan, he was blinded by the flash of a camera. Dan was taking pictures his cock in Peter's ass, and Peter kneeling with an erect phallus in front of his face.