Dean and the Tgirl

byM.MartineMatheson©

"Hi, it's Kelly," the sexy transgendered girl cooed when Dean picked up his hotel room phone.

"Just get in?" Dean asked. "How was the drive."

"It was quick -- I made good time."

"Bet your thirsty," Dean said. "Meet me in the lounge down there for a drink?"

"Would love to," Kelly said. "I'll see ya in a few."

Dean took a final look at himself in the mirror. He didn't know why he was so nervous. He had met this sexy Tgirl before in Pennsylvania and they had made love. He was nervous then because he'd never been with a man. Kelly was really a man, right? That was something Dean had struggled with. She was gorgeous with small breasts but definitely formed enough to be passable. She had no facial hair, smooth legs and a great ass. Long, sexy hair and eyelashes and the makeup she wore left no doubt about her gender.

The only thing that remained was her -- his? -- cock. It actually got a lot larger than Dean had thought when he stroked it in Pennsylvania. He had read the hormones got rid of facial hair and helped grow breasts but he thought it left cocks limp forever. Not so, said Kelly and some of the tgirls he had talked to online.

Some of them grew to as long as 8 inches. Some Tgirls could shoot cum across the room. It just depended upon the person.

Dean was so surprised at the hardness and smoothness of Kelly's cock that he didn't even think about touching it with his tongue. Maybe tonight.

He was also concentrating on penetrating her gorgeous ass with his cock, which he did, to both of their delight. But he had pulled out and came on Kelly's back -- he wasn't sure about cumming inside of her ass, although he had read about it and talked about it online with other Tgirls and the thought of it made him hot.

Who knew what would happen tonight? Who even knew if Kelly would stay over? Who even knew if they would have sex. I mean, Dean, thought, he really liked Kelly and he thought she liked him. It was only a 90 minute drive home for her. They may get a drink, have dinner and she may head home? He guessed he'd find out soon enough.

He checked his tight polo shirt and jeans one final time and headed down the elevator to the lounge. He couldn't wait to see what the sexy TG was wearing.

Kelly was sitting sexily on the stool when Dean spotted her. She wasn't at the bar -- she didn't wanna give off the impression that she was a hooker or someone there just looking to pick someone up -- but there were tall bar stools throughout the lounge at every tall table.

Dean saw her sexy, tan legs and heels and short skirt and immediately his cock jumped. Perhaps Kelly was dressing to please him -- if she was, he was certainly pleased.

He leaned down and gave her a kiss on the cheek and a hug and then ordered a couple drinks. The conversation flowed easily as they talked about their work and what they had been doing since Dean was in PA in early August.

Occasionally during the conversation, Dean's cock would jump at something Kelly would say. Occasionally she'd place her hand over his of he would do the same. They were getting a long well. Dean didn't want to interrupt the nice conversation by asking Kelly to dinner but he thought it best.

"Are you interested in getting a bite to eat, Kelly? There's a restaurant right here or we could order from the bar or we could go someplace else. Your choice? Are you hungry?"

Kelly had dressed with care for this rendezvous because she cared what Dean thought about her. She had grown up with teasing and torture, so kindness and gentleness needed very careful rewards.

After buying her Raiders T shirt, she'd stopped at her favorite store at the mall -Rave - and looked through the crammed racks. The clerks knew her as a her - as did mostly everyone in the town her family had moved to only recently. Her arms full of skirts and tops, she walked to the counter to ask for a dressing room.

"Right this way, Miss, how many garments do you have there? Eight? Fine...."

Kelly tried on and tossed away two skirts before zipping into a third. This one was a stretchy lycra skirt, very snug, and fitted her butt like a glove. It was short, too, and it showed off her great legs. She planned to wear her highest heels for Dean because she was a teense, and she thought he was over 6 foot tall.

For a top, she selected a long sleeved zippered hoodie sweater (like Dawn's photo) made from a soft yarn. Giggling, she tried on the small, but then selected the extra small. She thought Dean might like tight clothes. And zippers. She had two to show him tonight, if she got the chance.

Kelly tried her best to look grown up and sophisticated as she replied, looking directly in his eyes, "Dean, I am very hungry, thank you. Ravenous, in fact. But let's order a pizza and take it back to your room."

She loved the startled look on Dean's face, but she hadn't driven two hours to sit in a restaurant with such a lust in her skirt. She was sure he spotted the bump in her tight skirt when she returned from the ladies' room. At least, he seemed to let his eyes run over her body when she had returned, planted a chaste kiss on his cheek, and hiked her leg up to reach the barstool, so much higher than she could normally reach. Out of the corner of her eye, she was pleased to see Dean staring at her legs - her legs? - as she pulled herself up onto the stool. As she crossed her legs, his hand made contact with her smooth knee again. She covered his hand with hers and they kissed. When the kiss was over, both hands stayed where they were, and Kelly knew she would at least fuck this man, if not stay over.

"Let's go," Dean said, leaving a $20 on the table for the drinks and tip, and he and Kelly headed for the elevator. They both had read stories about elevators and so once the doors closed, Dean broke the awkward silence by saying, "May I?"

Kelly nodded her approval and Dean pinned her against the back of the elevator, kissing her erotically but a bit hard, more lust filled than anything. Their tongues matched each other's in her mouth and Dean pressed himself against Kelly, feeling her bulge against his until the bell rang and they were on the 14th floor.

Kelly straightened her skirt and followed Dean out of the elevator and down the hall to 1432. Once inside the kiss resumed, the lovers renewing acquaintances as they had in the PA hotel room less than a month ago.

"You're so gorgeous, so fucking gorgeous," Dean said between kisses, as they maneuvered toward the bed.

"You REALLY think so?" Kelly asked, wanting to be reassured.

"God yes, and so fucking sexy," Dean said, kissing her again.

He broke the kiss and fumbled for the phone book while Kelly nuzzled and nibbled on his ear. This gorgeous girl had made him so horny he was ready to get laid then and there, but if she was hungry, the least he could do was oblige her and get her a pizza.

Dean dialed the pizza parlor and started to place the order. While he was doing it, Kelly slid off the bed and knelt there and began stroking Dean's cock through his tight jeans. Then she unzipped her sweater to reveal her sexy breasts -- she had worn no bra.

Dean's mind wandered as he tried to finish the order and give the driver the address.

Kelly massaged her own breasts and then reached up, grabbed the phone, and said, "We decided we don't want a pizza after all. We're going to have dessert first."

Giggling, Kelly reached behind her with one hand for her large purse, and offered it to Dean while her other hand was rubbing the front of his jeans. He looked down at her, puzzled, but she ignored him as she unbuttoned the button and slowly - too fucking slowly, he thought, he was hard as a rock and the jeans were holding him too tightly - unzipped him. He looked through her bag because she seemed to want him to, and found what she wanted: a can of aerosol whipped cream.

Dean stood up and allowed Kelly to slide his tight jeans to the floor. He kicked off his shoes and socks and then Kelly's fingers slid inside the elastic of the briefs and they, too, came off. His cock stuck straight up, teasing the polo shirt he still wore. That didn't last long. He took it off, and there he was naked in front of her with a can of whipped cream in his hand.

He sprayed some on his cock, just a bit, and then thought, what the hell, and coated his cock and balls with the white cream. Kelly smiled, said, "mmm" and went to work...careful just to get the cream and none of Dean for a very long time. Then she grabbed the can and covered him again. It was amazing how she could lick the cream from around and on his cock with out touching it.

Dean was incredibly hard and could not wait for this gorgeous tgirl to get her sexy lips around his unit.

He pulled her to a standing position and they made out some more while he helped her off with her sweater. He grabbed the can, covered her tits with cream and went to work on licking it off.

he wasn't as careful as she -- nor did he want to be -- and soon her small breasts were in his mouth and the gorgeous tgirl was moaning.

Dean wanted to make their second encounter last as long as he could - he loved delaying his partners' orgasms until they fairly begged for release - so he knew it was time to throttle back a bit with Kelly. The hottie was getting far too worked up for the evening's fun...so Dean grabbed her and gave her a deep French kiss that left her reeling, and then stood her a pace or two away from him.

With the aerosol can of whipped cream, he drew a bikini on the girl, giving it straps, tiny cups, and covering her bikini area too. He turned her around and drew a thong across her butt, and asked her to bend over slightly, so he could line her ass with the cream, too.

She turned her head and faced him while he continued to spray the cream all around this sexy girls' body. Finally, he was done with her and stepped back and asked her to do the same for him. She only coated his cock and groin area and then turned him around and coated his ass, careful to spray some in his crack.

Then they engaged in another hot French kiss. Kelly tried to push Dean back onto the bed but the muscle stud would have none of it. He didn't want the cream to be messed up, not yet anyway. They made out for several more minutes until finally their cocks touched. Dean's 8 inches and Kelly's 6 were standing out straight in front of them.

The bodies of the lovers were apart but the cocks were touching and without any guidance from any hands, the lovers looked down and made sure the cocks touched each other, smearing white cream onto each other. Occasionally, they would share a deep kiss but then go back to touching cocks. The sight was hot and the feeling even hotter.

The shorter Kelly had kept her heels on when Dean stripped her, and now the sight of her, nude save for the whipped cream and heels, made Dean's erection even more rigid. Kelly slipped her waxed leg between Dean's as they kissed, and in doing so, her own stiff cock nestled in beside his. The lovers began a minute grind against each other, their French kissing devouring each other's mouths, as their cocks rubbed and slid against each other. Kelly lifted her leg slightly, and the pressure on Dean's scrotum nearly made him faint.

But dean was determined to make this visit to Cleveland memorable for both of them. He leaned down, licked some cream off of the right breast of the sexy Kelly and then stuck out his tongue, feeding it to her. She licked his tongue and French kissing continued. Next, dean licked some whipped cream off the right breast and they kissed again. this continued until the breasts were licked clean. Dean then moved downward to the magical area that generally held a pussy. This time his tongue ran into a stiff cock.

Dean expertly licked the cream from Kelly's cock. It was the first time he had a chance to really concentrate on it -- it helped that he was prepared and knew it was there. How could such a gorgeous woman have such a gorgeous cock, Dean thought, as he made love to it with his mouth and tongue. The cream all gone, Dean took the entire cock in his mouth and began sucking.

Kelly was holding on tight to Dean's head, whispering, "Baby, really you don't have to do this. I'm supposed to be sucking you baby, really."

Dean took the cock out, held it in two hands and looked up, smiling, "I want this cock, gorgeous. I want this magnificent cock in my mouth -- for now."

He went back to blowing Kelly and reached up with a free hand and caressed a sexy nipple. He loved how Kelly's brown hair fell over her shoulders and teased her bare tits.

Kelly wasn't going to hold out long. She whispered that she was close to cumming.

"Mmm" was all Dean could muster as he took the cock out of his mouth and began jacking it off furiously. He wanted to watch the hot white cum shoot out of Kelly's cock onto his face, his lips, in his mouth.

And shortly thereafter it happened. With a final stroke, Kelly screamed a femme scream, moaned a femme moan and came, a big glob of white luv juice spurting out. It made it to Dean's lips and he covered the cock with his mouth so the rest could be shot inside.

Kelly wanted to say something, how happy she was that Dean would satisfy her like that and how she wanted it to be her turn but Dean would have none of it. licking up her sexy body he tasted her tits, which were now free of whipped cream and moved up to kiss her lustfully. Kelly tasted her own cum as she had many times on her own. But this was different because it was is Dean's mouth.

The couple French kissed for a long while as Kelly got hard again. Dean sat back on the bed, pulled Kelly onto his lap, facing him and the kissing continued. Dean maneuvered Kelly into a position where her sexy ass was his for the taking.

Dean didn't think twice, allowing his hard member to slip into Kelly's ass for the second time in a month. The whipped cream on Dean's cock and on Kelly's ass served as lubricant and the lovemaking continued with the lovers looking into each other's eyes while they moved together.


Kelly held herself with one hand on Dean's strong chest, and the other behind her, on his thigh. Her eyes locked on his, she reveled in the sensation of his huge cock up her ass, every nerve screaming its appreciation. She loved his this man felt inside her, how he filled her and made her gasp - not once, but several times - as he gently thrust up into her. She looked away briefly and saw her own cock rising. She could jerk herself off - some men liked to watch that - but she was silently praying Dean would take her smaller cock in his hands and complete her passion.

Dean steadied the pair so they wouldn't fall off the bed and continued fucking his transgendered prize. How he could've stumbled on a gorgeous tgirl like this was amazing. Most of them were ugly men-looking types, he thought, as his cock filled this ass. This wasn't like fucking a guy at all, he reminded himself as they made out, her tongue soft like a female's. Not at all, he thought, as he massaged her sexy tits and rolled her nipples between his fingers. even her cock was femme, and he began stroking it with one hand, then both. It was wet from the cream and lubed up so it slid easily between his hands and fingers. She moaned as she was ready to cum again. Dean was ready, too.


Kelly loved it when Dean began to gently pull on her cock, hand over hand, letting it slip through his clasped hands one by one. She was bouncing on his cock, now, forcing it deep inside her, making it hurt her just enough, as Dean's hands lifted and pulled her cock away from her body. she was about to explode and she knew he was, too.

"Dean...Dean!..." she murmured urgently, a gutteral moaning of this god's name. He knew she was cumming, and he loved looking into the pretty face of this toy who seemed to delight in being used by him, as she lost control. He was looking directly into the face of ecstasy, and he had caused it, he had prompted it, he had inspired it.

The final stroke of Kelly's cock brought her second ejaculation of the evening, high onto Dean's chest. In fact, he pointed the cock toward his mouth but the stream didn't quite reach it. He leaned down in an effort to catch some of the cum but his try was in vain as it landed on his chest and rolled down his stomach and between his legs.

But the thought of the hot white cum on his body brought him to the edge. He thrust his cock deep into her sexy ass one final time and spurts of love juice followed, filling the darling tgirl as she moaned with ecstasy. Dean's throbbing cock continued to fill Kelly and the seed shared the space in her ass with his gorgeous cock.

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