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Dean and the Tgirl

Author: M.MartineMatheson
Category: Transsexual_Stories
Last updated: Feb 21, 2008

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"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.


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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.

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