Had [M]y way with a virgin sissy in a Dallas hotel room

Playing with people on Reddit is damn near impossible. If you find someone near you or just willing to play virtually there is a higher than they flake out than on any other platform. Fetlife or Tinder are much easier. But there are less people on Fetlife and less kinksters on Tinder. So I end up here.

Lena was posting pics when she first caught my eye. This wasn’t the normal guy in panties stuff. These were full blown photo sets from the lips down. Skirts. Blouses. Dressed. Heels Stockings. Lingerie sets with matching garter belts. It showed dedication. I noticed we were in the same city. And so I messaged and we started chatting.

Some elements of her story were typical. She liked to dress up. She was curious about men, but had never been with one in any capacity aside from a little oral exploration, but that was way back in college before she started dressing up.

I was more fascinated by the atypical things about Lena. That she’d first started crossdressing when a girlfriend has requested it. That the woman had taught her how to dress and do makeup. That she’d been fucked with a strap on regularly.

Lena had chatted with men before, but never anyone local. She fantasized about meeting. About sucking cock. About meing manhandled. About being used like a woman. She wanted someone experienced and I ensured her that I was. At the time I was coming out of a long term fling with a cross dressing young cuck and his wife.

It was obviously that Lena was ready to take the leap. She was hesitant, but at the same time eager to meet. I think she was she would chicken out and miss the opportunity.

I told her the expectation was that she arrived fully dressed. That made her nervous since she’d never left her apartment as a woman. I insisted and then she disappeared.

A few days later she sent another text. She really wanted to meet, but she couldn’t do that. I came up with a compromise. I booked a room in a downtown high rise. I checked in first and then left the room with the door propped open. I texted Lena and she went to the room. I gave her an hour to get dressed.

From her pics I knew she was Hispanic. She had a slender, hairless body an full lips. But I’d never seen her full face. I was pleased when I went into the room. She wore brown chin length bob wig and had sexy brown eyes with full lashes and eye liner. Her lips were ruby red.

As requested, she was dresse as a naughty secretary in a tight black skirt and thin white blouse with her red bra showing through. I knew from experience that things could get awkward if I didn’t take the lead. We’d agreed beforehand that we were going all the way and I wasn’t going to let Lena change her mind.

I took her hand and pulled her toward the bed. I commanded her to her knees. I sat at the foot of the bed and told her to suck my cock.

She fumbled with my zipper. She was obviously nervous. She licked my shaft tentatively. She wrapped her lips around the head. It was clumsy and didn’t do much to please me. But I was still rock hard.

“I thought you’ve been practicing on toys?”

She told me she had.

“Then why don’t you know what you’re doing? Have you ever had a blow job, Lena?”

She assured me she had.

“You need practice. You need to be taught to please a man. And I don’t have the patience today. Let’s just fuck.”

She started getting nervous and said she wasn’t sure. That maybe we should just do a blow job for the first time. My cock isn’t huge, but it was obvious that she was still a little worried by it.

“I didn’t pay for an expensive hotel room to get a blow job,” I said.

She said she could pay me back or we could split the room. She was in her late 20s and I wasn’t sure of her finanical situation. I knew she lived with a roommate, so maybe half of a $350 room would be a lot.

“You can pay me back by giving me what I want,” I said.

She started to stammer. I reminded her that she wanted to be manhandled. Now it was going to happen.

I stood up and pulled her to her feet. She couldn’t have weighed more than 140 pounds, so I had a strength advantage. Not to mention she was unbalanced in her black high heels.

I roughly bent her over the bed and started shoving her skirt up. She was rock hard in her silky little panties and I rubbed her prick. She started to whimper.

“You know you wanted this,” I said. “You dressed up like a whore for me because you want my cock.”

She nodded her head.

I rubbed her again through her panties.

“You’re fucking hard because you want this.”

She assured me she wanted it in the future. But she wasn’t ready for it.

I pinned her to the bed and pulled her panties down. I took a small bottle of lube from my pocket and dribbled it in her asshole. I started dry humping her. Grinding my hips into her ass. Forcing her cock to rub the into the bed. She kept moaning with delight and whimpering.

“Will you use me?” she asked.

I got a rubber on quickly and forced my way into her tight ass.

At first she was a dead fuck. It’s like she wanted it to be over. But I took my time. I fucked her nice and slow and eventually she started moving with me. She moaned with pleasure.

“Use me,” she eventually whimpered. “I’m your whore. I’m your naughty whore.”

I surprised myself with how long I lasted. She was incredibly tight and once you she got into it she moved like a pro. At the end I pulled out and made her jack me off and take my load to the face.

Afterwards I told her to get dressed–like a woman–and walk out the door and get in her car. Failure to obey would mean I never see her again.

She did it without talking back.

Source: reddit.com/r/gonewildstories/comments/b3uocz/had_my_way_with_a_virgin_sissy_in_a_dallas_hotel