Vanessas Erpressung
- 2 years ago
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This is a memoir of my first time meeting a man.
I’d been crossdressing for many years. I had many fun nights dressing up and playing with my toys but I wanted something more. I liked to get on the phone with guys and play around. I had my favorite toys to use, especially my eight inch dildo and my butt plug. I really got into my phone sessions, but I felt like I wanted to go further.
There was a nice guy who I had been talking to for a while, and I got to know a little better than the average phone fuck. He was friendly and sweet, and made me comfortable.
One night, he finally asked me if I wanted to get together. I was surprised it took him so long to pop that question, but maybe that was why I felt so comfortable with him. I was nervous, but I decided that it was time to give it a shot.
We agreed to meet at a local motel. I got dressed in a sexy tight, mini-skirt, blouse, garters, stockings, lacy bra and thong, and five inch heels. I did my make up nice and sexy with red lips and nails. I looked so slutty, and I wanted to make this guy’s jaw drop.
We pulled up to each other in the parking lot as agreed. We wanted to make sure we were both comfortable before going any further. One look was all it took, and we agreed that he would go get us a room. He came back and we walked into the room together. We stood there for a few minutes, a little bit nervous. He had some booze, so he poured us both a drink to loosen us up. Then, after talking for a little bit, he asked me if it would be okay if he took down his pants and showed me his cock. I told him that I’d like that, so he did. It was about six inches and thick.
I reached out to touch it. It was so strange, but such a turn on. I had never felt another man’s cock in my hand before, but I liked the way it felt. I liked hearing him moan as I stroked it, and got it harder. We moved over to the bed, and he pulled my skirt up and moved my thong over so he could stroke my already hard cock. We played with each others’ cocks for a while, enjoying each others’ moans.
I wasn’t sure where this would lead, but I figured I might as well go one step further. I was about to put my mouth on his cock when he exploded his load in my hand. What a disappointment! Not wanting me to leave without having some fun, he asked me to do what I would normally do. Good thing I brought my big eight inch dildo with me.
I lubed myself up and began fucking myself with it, until he grabbed it and took over. He fucked me with that dildo so good. It was the first time I had another person use it on me, and it was so hot. I told him, ‘Next time I want that to be your cock inside me,’ and he fucked me faster with it.
I was fantasizing about him fucking me, and shooting his hot cum deep inside me. He kept it up until I shot my load all over myself. We talked for a bit and got cleaned up. I drove home that night feeling a little tense, but knowing that I took that next necessary step into my girlhood.
When I got in, I looked at Vanessa in the mirror and enjoyed the memory of my first cock.
“Come on over here and get comfortable while I think up a story,” I suggested to Vanessa. “I know I’m not allowed to play with your pussy while I tell it, but what about your boobs. Can I play with those. I need something to inspire me.” “Well,” Vanessa considered, “normally that would be totally against the rules. But if you admit that you have lost totally already and that I am the absolute winner, then all rules can be suspended.” “Oh, hell,” I conceded, “you romped it in. Against your...
Vanessa leaned back against me in the bath as I played casually with her soapy nipples. She turned her head and kissed me lightly on the lips. ‘Isn’t this bliss?’ she sighed. ‘I love bathing you,’ I said, ‘but I can’t wait to dress you too. I love the feeling of looking after all of your body’s needs.’ ‘All of my body’s needs?’ laughed Vanessa. ‘Next you’ll be wanting to wipe my arse for me after I take a shit. Hey, I felt your cock twitch. Don’t tell me that thought turns you on.’ ‘It’s a...
The afternoon sun was streaming through the bedroom window when I awoke from a dream that Vanessa was casually and luxuriously sucking my cock, to find that she really was casually and luxuriously sucking my cock. ‘Hmmm..mmm,’ I sighed contentedly, ‘nothing like waking from a wet dream to find a wet reality.’ ‘Well reality’s not the only thing that’s wet,’ she replied. ‘I’ve been playing with myself again but it’s no substitute for the real thing. I hope you don’t mind that I started getting...
The next day I had set up my easel on the beach outside my cottage and was once more attempting to paint a landscape that someone might actually want to buy. Once more I was failing miserably. My heart just wasn’t in it. “Howdy, neighbour,” called Vanessa as she strolled up the beach towards me. She was wearing a navy blue short-sleeved blouse and white pleated skirt that fell just below her knees. When she reach me I noticed that her blouse was undone just enough to reveal that she was wearing...
Vanessa’s phone call woke me from a deep sleep. ‘You’d better stay up your end of the island for the next half hour,’ she warned me. ‘I’m going for a swim.’ ‘Thanks for the warning,’ I replied. No sooner had I hung up the phone than I grabbed my binoculars, positioned on my bedside table for just such an emergency, and ran down the path to Vanessa’s beach. I didn’t bother to put on any clothes. After all Vanessa wouldn’t be seeing me, or so I thought. Fifteen minutes later I had taken up my...
At first it seemed a bit strange to be reading aloud a story written in the first person by a woman. But somehow, knowing that Vanessa had written the story, I found it a tremendous turn-on. It was as if I was not just possessing her body from the outside as I had already, but from the inside. When she played with her body or the bodies of other women in the story it was with my hands. When she saw them it was with my eyes. ”I run a health club for women only’,’ I began. ”Alot of women would...
‘Does it feel good when I do this?’ Vanessa asked, briefly clenching her pussy muscles around my cock as she pumped up and down on it. ‘It feels like your pussy is wanking me off,’ I cried. ‘My pussy is wanking you off and sucking you off and fucking you all at the same time. Isn’t she a naughty, clever little pussy,’ she explained, her voice quavering and breaking in the ecstacy of the fuck. I grasped the cheeks of her bottom, wet as they were with freely running sweat, and rolled her over...
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