[MF] Becoming “naked friends” with a woman I met online – Short Sex Story

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I travel a lot for work. This leaves me with lots of lonely nights in hotels, and hotels all the time make me horny. So, if I’m being honest, there are some nights I don’t spend alone…

I’m not the type to go out to a club, and I prefer talking to people. Conversation and getting to know someone, even if superficially, is what turns me on. Plus I tend to better with women when I can communicate, rather than just shouting “what?” in each other’s ears.

Plus, as much as I do love variety (and I do, sue me…) I also do like getting to know someone sexually, and not just having repeated one night stands. When I connected with this woman on a dating site she was disappointed to learn that I didn’t live in her city. We’d already flirted quite a bit, and had established interest in one another, but she was hoping she was gonna discover someone who lived in town.

I reminded her that I would be a frequent visitor and can be a fun friend until she finds the long term relationship she was looking for, and followed it up with a Wink emoji…
“Oh really?” she replied. “What kind of friend?”

“Well, a lot has to go right for us to get to this point, like will we have the same chemistry in person, will we be attracted to one another, but if that all goes right I think we’d make excellent ‘Naked Friends'”.

She laughed at that and asked “and what is involved with being ‘Naked Friends’?”

“Well, when I’m in town, we go out for drinks, flirt like crazy, and if the mood strikes us we go back to my hotel and get naked. When I’m not in town, obviously you owe me nothing and get to continue your quest to find your boyfriend. All I ask is that when you do find him, you tell me, and you don’t just ghost me…”

“Interesting. This is intriguing enough to give it a try…”

So we continued to get to know each other, but this time with a distinctively more sexual tone to it. We talked about experiences we’d had that were incredible, and others that were less than amazing. We talked about fantasies, and things we might be open to trying if the whole ‘naked friends’ thing worked. And we established ground rules (one of hers being that we don’t do booty calls. If we are gonna fuck, we spend the night together.). We quickly found we were on the same page with most ideas, and then started to distribute more pics.

This was pre-reddit days for me, but I certainly wasn’t shy. But I also enjoyed making a woman ask for the pics she wanted versus me sending something too early. We got to the point where she finally asked, “So you’ve hinted you are reasonably well-endowed… do I get to form my own opinion?”

I laughed and asked “would you like to see?”

“Mhmmm” was her reply.

I sent a pic that I liked that I wondered accurately represented what I had to offer…

“Oh my, yes. Naked friends is going to be fun” she send back quickly.

At the time I was working for a professional sports team and I offered to get her and a friend tickets to a game the next time I was in town, then she and I could go out for drinks after the game. The night of the game she texted me that she’d just sat down, and I went up to meet her and her friend at their seats. This was our first time meeting face to face, and I’m sure everyone was a little nervous and awkward.

I hugged her at her seat and told her she looked great, then reached to shake her friends hand.
“Nice to finally see your face after we’ve all seen so much of the rest of you!”

I laughed and I’m sure I blushed a little too. I was flattered that my friend was sending my pics to her friends and not at all offended or worried.

I told them to enjoy the game and we worked out the plan to meet up at a bar around the corner after.

About 5min later I got a text from her saying “You look hot in your suit” with the purple devil emoji that we all now know to mean “I’m horny”.

I replied “You look great too. I think we moved to the next level of Naked Friends”

After the game ended I met up with her and her friend at the bar. She let me know that her friend was gonna stay for a little while but if everything went according to plan would be making an early exit.

I bought a round of drinks and the friend of my friend, clearly drunk, asked “so did I embarrass you with what I said when we met?” She was obviously trying to needle me again.

“Not at all.” I replied. “I know I’ve got a great cock and I’m flattered Cindy shared the pic.” That seemed to shut down the friend that I think was hoping I would be embarrassed. From that moment on it was conversation between my friend and myself, and the 3rd wheel made her exit a few minutes later.

Cindy leaned in at one point, my hand already on her leg… “You remember me telling you one of my fantasies?”

I knew exactly what she was referring to but played dumb, and she knew I was being cheeky..

“Which one?”

“Remember how I told you I’d always wanted to be fingered in a crowded bar?” she said as she placed her hand on top of mine, which was on top of her leg. I leaned in to kiss her and ran my hand up her thigh. She parted her legs as if to say “Yup, that was a signal…”

She’d picked a good location to sit, with a wall on her one side and me standing on the other side of her. She turned her body slightly towards the wall and moved up on the stool, spreading her legs slightly more. My hand worked up her thigh and found her panties. I teased her pussy over top of her panties and she looked at me with lustful eyes, bit her bottom lip and gave the slightest nod…

After teasing her pussy over her panties for a couple of seconds, I moved her panties to the side, ran three fingers up her pussy, using the outside two to spread her lips wider so that the middle finger found her wetness first and her clit second. I teased her clit for a couple of seconds, before sliding my hand back down and sliding my middle finger into her pussy.

Had anyone been watching I wouldn’t have taken much to find out what we were doing. She was sitting in a totally unnatural way, I was awkwardly standing beside her, she seemed to be in sexual bliss, and my arm was moving back and forth. I added a second finger inside her for several strokes before I whispered in her ear “we’d better get out before we get kicked out.” Without missing a beat she stood up and straightened her skirt, and we quickly exited the bar.

My car was parked a couple of blocks away and we enjoyed a bit more privacy on the walk. There were a couple of different times we stopped on the walk so that I could continue what I’d started, leaning her up against a wall and sliding my hand up her skirt to fuck her with my fingers again.

When we finally got to my car, she reached across to massage my cock over my pants. “Fuck, it feels thick…” she said.

“Would you like to see?” I asked. She nodded.

I unzipped my pants and pulled out my cock.

“Jesus Christ” was her reply.

Now, I should say… being seated put me in the best position to show off. Somehow when I’m seated (and I’m sure it’s the same for all men), there is pressure applied to the taint that forces more blood into my cock. Long story short, my already big cockhead looked HUGE.

She didn’t miss a beat. She leaned forward and quickly took my cock in her mouth for a second, then sat up and said “Your hotel better be close.”

I couple minutes of driving with her blowing me expertly and we were at my hotel. I quick finger fuck in the elevator, and before long we were in my room quickly removing each others clothing.
We were both naked by the time we hit the bed, and there was no need for any more foreplay. We were both ready. I was leaning her back on the bed, she was reaching for my cock as I crawled between her legs, and we both guided my cock into her soaking wet pussy on the first thrust.
You know those times when you have sex and you want to delay your orgasm as long as feasible?

You want to savour the moment and enjoy every moment along the way? Those sessions are super hot.

THIS was not that. We were almost in a race to make each other cum as soon as we could. After weeks of chatting online, and the time in the bar/walk/car, we’d had enough create up and craved the release, and each knew the other person wanted it just as bad.

I took her hands and pinned them over her head as we fucked in missionary. Then I changed the angle of my hip, lifting them slightly higher so the shaft of my cock would hit closer to her clit as I stroked in and out of her. That seemed to do the trick…

“You know you have the perfect cock, don’t you?” she said in my ear. “You’ve heard it before and you know it’s amazing…”

She was right, I had heard it before, but I all the time assume women are just saying nice things in those moments. Regardless, it was hot to hear.

We kissed as we fucked, her hands still pinned over her head as our naked bodies moved together.
Then I rolled over sensing that she was close to cumming but needed to take a little control to get herself over the top. She guided my cock inside her pussy as she straddled me, then leaned forward into my hands on her breasts. “Jesus Christ” she repeated. “Naked Friends was an excellent idea.”

We smiled at each other briefly, gave a quick laugh at the honest of the moment, then got back to work. She leaned further forward so her chest was against mine, my hands found their rightful place on her ass and squeezed tightly, and she grinded on my cock as she road. This was enough to get her over the edge and she started to cum.

I took over the thrusting as she lost control, trying to maintain the rhythm she’d created. Once she came down from the high over her orgasm, I started to sit up, and she instinctively moved off me.
I got up on my knees and she bent over on the bed, and I hand my hands down her back and over her ass. She looked amazing bent over for me. I took my cock in my hand and one of her hips in the other and pushed back inside her. “Oh Fuck, that hits great spots” she laughed as I slowly started to stroke in and out of her.

The hand on her hip remained, but my other hand ran up her back to her shoulder and used it as leverage to pull her back into my thrusts.

“Your back looks amazing, and your pussy feels so good” I told her. “I’m not going to last long like this.”

She leaned forward so her elbows were on the bed and ass in the air for me. “Good, I want to feel you cum.”

With that, I increased my tempo. With each thrust I tried to push was deep inside her as I could, now that I was confident she could handle it.

It was only a minute or two before I felt my orgasm building. I could feel my thick cock engorge with more blood, and then I had the moment where my body had to stop for a second to start to cum. “Fuuuuuuuck” was all I was able to utter as I came with several spurts deep inside her pussy.

She collapsed on the bed and I fell on top of her, still breathing heavy. My cock continued the small spasms that follow a great orgasm, then slowly started to slip out of her.

That was the beginning of a fun Naked Friendship…

NSFW: yes


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