[F]light attendant [M]ilked me dry on her layover

[F]light attendant [M]liked me dry on her layover

This happened a little over six years ago now. At the time I was in my late 20’s and in university. To paint a bit of a picture of me at the time, I was around 6’1”, 195 lbs, light brown hair, and decently built.

I’ve never been the type to go out drinking on weeknights, whether as a full-time student or working – I just don’t function well the next day, so I generally avoid it. During my second year of university however, I had a roommate who was a high functioning alcoholic. Needless to say, every day was an excuse to party for him. On one particular Wednesday, he suggested we all go downtown for some drinks. I had two exams the next morning, one for a for a course I was borderline failing. I would have normally declined the invitation. However, my other roommate who was in a long distance relationship and went out even less than I did obliged, so I decided to go along with it. After all, it was just going to be a few casual drinks.

We arrived at this popular hipster bar in town, which I could never quite understand the appeal of. I got myself a beer and blended in with the crowd, enjoying the atmosphere as best I could. I didn’t have any intentions for the night other than have a couple of drinks and be social.

Not too long after doing a bit of people-watching, I noticed a woman in her late 30’s standing alone with a drink in her hand. She had medium-long light brown hair, and average height and in decent shape. She was dressed fairly casually, wearing a black and white striped shirt – which was not at all revealing, but fit just well enough that you could tell she had a nice sized pair of tits hiding underneath.

Again, without any real intention, I approached her and started some small talk, likely asking something not very interesting like “what brings you here?” She introduced herself as Paris, and that she was a flight attendant in town for the night for a layover. We didn’t click instantly by any means, but had no trouble keeping a conversation going. Eventually her and my group (myself, two roommates and the functional alcoholic’s girlfriend) blended together chatting the night away. At some point, another random dude who was seemingly at the bar by himself as well found his way into our circle.

By the time last call was nearing, I had maybe three drinks in me – giving me just enough momentum to keep going, wherever the night would take us. Paris wanted to keep the party alive, and invited us all to her hotel room a few blocks away where she had some spiced rum awaiting. After a bit of deliberation, our group (including the random guy who no one really paid much attention to) decided to go along with it.

We arrived at the hotel room, poured drinks and spread ourselves out amongst the two beds and furniture. It wasn’t much long after that when things started getting interesting. Somehow or another, the girls got on the topic of boobs and nipple sizes, and comparing theirs. Alison (roommate’s girlfriend) had a smaller pair, probably an A or small B cup, while Paris would be about an E cup. Alison was eager to see Paris’ larger nipples, and the rest of us pressed on for them both to take their tops off. Unfortunately we didn’t get a show, but the girls did go into the bathroom together to compare their tits…which sounds stranger now that I’m writing this, but that’s how it went down. No girl-on-girl action unfortunately.

It was getting late in the night and everyone was about ready to pack it in, including me. We all got up to head out the door – while random guy was visibly awkward as he was clearly hoping for a shot with one of the girls. As we were making our way to the door, Paris looked at me directly and said quietly “I want you to stay”. Holy shit, so this is happening I guess. I silently agreed, and we all headed down to the hotel lobby, where I stuck around with Paris while she had a cigarette.

After her smoke, we headed into the elevator. Despite her clear signals at this point, there wasn’t really a whole lot of flirting and tension built up between us, and I felt a bit nervous as I pulled her in for a kiss as the elevator rode up to our floor. We got back into the hotel room and quickly got to business. As clothes were coming off she asked “Do you have a condom?” I replied “No, I don’t normally carry them on me”. I certainly didn’t expect I would be at a hotel for a one night stand on a Wednesday night. Paris immediately looked disappointed, as she said “shit…I was really looking forward to fucking you tonight.” She wanted to get off still, and proposed we mutually masturbate.

Paris laid on the bed naked, legs spread rubbing her shaved pussy as she instructed me to talk dirty to her. To be honest, I wasn’t well versed in dirty talk at this point in my life and quickly ran out of material. She wanted me to talk about how big my cock was, and I couldn’t come up with much more than “you like this big cock? Do you want this big cock?” Besides, the only thing I could really focus on was the beautiful pussy spread in front of me and her huge tits. Kneeling on the bed in front of her, I did my best to put on a show for her while working to get myself off as well. Between the liquor and feeling of awkwardness, my cock was not quite at its full erect length of just under 8”. I couldn’t see myself cumming anytime soon doing this. I don’t think she was going to get there, either.

I inched myself closer to her glistening pussy as I stroked myself. I teased the entrance of her pussy with my cock, rubbing her clit with my head and carefully watching her fight the urge.

“We can’t…” she moaned. I pulled back and we both kept rubbing ourselves as the temptation continued to escalate.

I inched toward her again a minute later, bringing my cock closer this time and pressing the head into her pussy. She gave me a devilish look as I rubbed my head along her opening, carefully watching her reaction and pulled away again.

I continued this for a few minutes, each time pushing my cock in a bit further, until finally I got past the tip. I worked myself in, going deeper with each stroke until the full length of my bare cock was in her pussy.

From this point on she was insatiable. I lasted longer than I expected for the first round – the alcohol must have countered the foreplay. She offered to put a finger in my ass as we were fucking, to which I declined (it’s not really my thing) but appreciated the gesture. As I was getting close to cumming, she asked me where I’d like to cum. “How about I cum in your pussy” was quickly (and rightfully) met with “are you fucking crazy?” I pulled out and covered her large natural tits with my load.

As much as I would like to divulge all the remaining details, all of the positions and such from the rest of that night, much of it is blurry to me now. There was no oral sex from what I recall – just straight fucking. We ended up fucking late into the night, with me cumming 3 or 4 times with little rest in between.

We were lying on our sides for the last round of the night. I felt an orgasm coming on, and pulled out to unload onto her body. “Did you just cum in me?” she asked, as no cum made it onto her. “No, I don’t think I have any cum left”. Her pussy had milked me dry.

I woke up the next morning with a slight hangover and feeling groggy from the lack of sleep. Paris was already ready for another round, but after having a dry orgasm not too long before, I literally didn’t think I was physically capable.

Paris was adamant about fucking again, and I (like most guys) was not the type to say no to sex. I stood up by the edge of the bed as she scooted down, opening her legs for me. I was still soft, and wasn’t really sure if I was going to be able to perform. As I brought my limp cock close to her pussy however, I felt the heat coming off of her and my cock’s instincts kicked in. I quickly got just hard enough to penetrate her once more. I surprisingly didn’t last long, either. After a few minutes of pumping her in this position, I pulled out and emptied what little cum I was able to produce overnight onto her stomach. I was completely drained.

I rolled back onto the bed next to her, spent. She massaged my cock and empty balls while we lay there, as if in a trance repeating “such a beautiful cock”. I was stuck between a moment of pure bliss and anxiety, as I had an exam to write in a couple of hours. I insisted I had to leave, and she begged me to stay and fuck her more until her flight that afternoon.

Eventually I was able to get myself up to leave. As I was heading out the door, she gave me her number and asked that I come back after my exams to fuck her at least once more. “You’re not going to be one of those guys that never calls back, are you?” she said. I’ve never been one of those guys, but for some reason I knew I was lying when I said “of course not”.

I walked back home, disheveled. Despite being in good shape and going to the gym regularly, every part of my body was sore from the night before. My arms, ass, abs, legs all felt like they had gone through an intense workout, and my nuts felt completely empty. I realized when I got home that she left a hickey on my neck, and deep scratches on my back and shoulders – which almost got me in trouble with a FWB I had seen the following weekend.

I never did message her, which I later could hardly reason why. I think it was a combination of guilt (I had one or two other girls I was seeing), plus she did seem a bit crazy. I feel like an ass for not following up, and I definitely missed out on more mind blowing sex. It would have been a good arrangement, with her flying in every so often for hotel sex. Good memories though.

Source: reddit.com/r/gonewildstories/comments/k98zt3/flight_attendant_milked_me_dry_on_her_layover