Anonymous Blindfolded Sex with a Stranger (F/M) | 2016

I am a curvy woman in my mid -thirties with long light brown curly hair and big hazel eyes. I have always been a very sexual woman and have been lucky enough to have had the opportunity to have a lot of fun and interesting sex. This story takes place about 6 months ago.

I learned a long time ago that a quick and easy ego boost was to put up a casual encounters post on Craigslist. With the added bonus being, that I might actually end up getting laid. The first time I did it, about ten years ago, I was a few months out of a long term relationship and not ready to date but really ready to have sex. I got over a hundred responses in one night! Mostly a ton of dick pics. Oh so many dick pics. I weeded it down chatting and exchanging messages with a few guys until I found a guy to meet up with for a drink and then go back to his tiny apartment and fuck. The sex was mediocre but he gave me a CD of his band that I have on my ipod and still listen to. It’s really good!

Over the years I have posted a number of ads. Often it’s when I’m healing from a breakup or feeling really down on myself or if I really need to have sex and don’t have any other good options. Sometimes I follow through and meet someone and fuck them, sometimes I just have fun and get an ego boost out of chatting and flirting and sexting with random guys. I have also met a few good, respectful, and fun long term casual sex relationships. Had a bit of really fucking hot random sex. And a fair amount of really boring stupid sex too.

About 6 months ago I woke up horny as hell and had this awesome masturbation fantasy. In the fantasy, I go into a hotel room, all dressed up in stockings and high heels and a short dress. I walk across the room and start to undress. I can’t see him, but I know there’s a man in the bathroom watching me. I have in fact never seen him before and, if all goes according to plan, I will never see him at all. I take off all but my panties and drink a glass of wine. Then I put on a blindfold and lay face down on the bed. I call out that I’m ready for him and he comes in. He touches and massages me all over with oil. A real massage, a sensual massage, getting more and more sexual and ending with some sweet penetration.

Then he goes in the bathroom while I get dressed and leave. Not once having seen his face.

Hot fantasy, good orgasm. I decided that it would be fun to post this fantasy on Craigslist and see if I got any takers. Turns out, I did! About the usual 100 in a night. I wasn’t sure if I was actually going to go through with meeting any of these guys but knowing that my private fantasy was a source of jerk off material for men I’d never met turned me on. Same reason I like to post on gonewild and why I’m writing this, of course. I sorted and weeded through all the messages. Discarding any with dick pics or body or face shots, the fantasy was to not know what he looked like. I didn’t want to know his age or ethnicity or anything. I threw out anything creepy or that I got a bad vibe from. I had put some rules and stipulations in my post about absolutely must use condoms and someone will know where I am and it will be at a hotel and my phone will be ready to dial 911 and I reserve the right to end it abruptly for any reason at any time (and so could he, and should he, take all the same precautions). I wasn’t up for anal or kissing or receiving oral sex, but I’d happily suck his dick if he wanted to put it in my mouth. I’d never not met an online date for the first time in a public place before, I’ve always taken all of those precautions with casual hook ups. And I’ve always been lucky enough to not have anything really fucked up happen. Even so, I knew this was a new level of risk and up until the moment it happened, even with all my rules and precautions, I wasn’t really sure I was going to do it. Until, I did.

I agree to meet this guy at a hotel at 9pm. I shaved and washed and all and everything. I wore black stockings, black lace panties and bra, short sleeved, low cut short black velvet dress, black high heels. It was cold, it was December. I waited in the car till he texted that he was ready and the room number. I went up the elevator feeling giddy and like a hooker and incredibly excited and nervous and turned on. My lipstick was red in the elevator mirror and a middle aged couple got on with me but got off on the first floor. I felt like they knew. I got to the room and pushed open the door that he’d propped with the dead bolt. I knew he was in the bathroom, I knew he was watching me. He’d lowered the lights and had a laptop computer opened on the table. There were sticky notes all over the room. The one on the computer said, “pick a playlist”. He’d made a few, I picked one and it started playing, some sort of thumpy trance. It was perfect. There was an open bottle of wine and a wine glass with a note that said “drink me.” I poured a glass. On the mirror was a note that said, “undress here. Leave your stockings on.” I undressed slowly, taking my time, drinking my wine. Down to my stockings. I had brought a blindfold with me; I put it on and lay face down on the bed. I called out, “ready.” And I heard him come in.

I had no idea who he was or anything at all about him. He didn’t speak but just started to touch me. First my stockinged legs and ass, my feet. Then my back, my neck, with the oil. “You have an amazing ass.” He said and I thought he had an accent, maybe German? I didn’t reach out to touch him but he sat on my butt and legs as he rubbed me and I could tell he was thin, not a big guy. He rubbed his hard cock against my stockinged ass. At first with his jeans on, then just his skin. He dug his hands into my thick hair and rubbed my scalp, pulled my hair, while he humped me. Eventually he pulled off my stockings and my panties and started rubbing my ass and pussy, and sliding his fingers in me.

Then he flipped me over. He told me I was beautiful and that my breasts were beautiful. Those were the only things he’d said to me, I hadn’t said anything. It was just our breath, faster and faster. Our moans. Then he asked if I wanted some wine, I nodded and he helped me sit up and put the glass to my lips and helped me sip it. I lay back down on my back and he started to rub and touch me. My legs, my breasts, my tummy, my pussy. He asked if he could suck my nipples and I nodded. He sucked and rubbed and fingered my nipples. I was moaning and writhing and I had no idea how long all this had been going on. It felt like forever and I felt like I was about to explode.

“I’m ready for you fuck me,” I whispered, “do you have a condom.” He said yes and got up for a moment. When he came back I touched his hard cock and it was wrapped. He mounted me and penetrated me. It was hot and heavy and fast and slippery cause of all the oil. I was on the edge of ecstasy already and after a few strokes I was over that edge and having and incredible orgasm against his pelvis without even touching my clit (unusual for me).

He fucked me for a few more minutes then I noticed he’d gone soft.
I asked if he’d come and he told me, “I came on your stockings while I was rubbing against your ass cause it was so fucking hot.” I found it a real turn on that he’d been so aroused just touching and rubbing against me that he came.

We lay together breathing hard for a few moments. I had my head on his chest. His thin, hairless chest. I reached up and felt his head and found longish, thick, wavy hair. I reached down and felt an uncut cock between hard, thin, hairy legs.

“It’s really weird to have had this blindfold on for so long.” I said.

“You can take it off if you want,” he told me.

“I don’t know if I should.” I said.

“You should.” He said.

So I lifted it and peaked at the man who had ravished me for the last 3 (yes three!) hours. He was young, very young. I would have said 18 but when I asked he told me he was 21 and he had bought (or at least brought) the wine. He was East Indian, thin, hairless, dark. And very cute. Big deep brown eyes.

“Hi,” I said.

“Hi,” he smiled.

I got up and said, “so, I’m gonna go.” I started gathering my things.

“No, no,” he said, “stay and watch a movie with me. I have the hotel for the night. Stay with me.”

“No,” I said, “it ruins the fantasy. I’ve got to go. “I put on my dress without my bra or panties or stockings. I tossed my panties to him, “you want these?”

“Yes!” He said.

“K. Bye.” I ran down the hall and down the back stairs and out the back doors, carrying my bra, stockings, cell phone, car keys, and high heels. Ran through the icy parking lot and jumped into my car. Laughing hysterically the whole way.

The last time I heard from him was a few months ago. He sent me a pic of his hard cock. With my black lacy panties wrapped around it.