Current location: Southern California
Highest education received: Some college (currently in college)
Occupation: Student and tutor
Relationship status: Married, getting divorced
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Heteroflexible, mostly interested in men
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0
Cheating With Each Other
How long ago did this hookup happen? 3 days ago
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? First hookup of possibly more
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? We’ll call him Drew. Drew is half Mexican, half Japanese, and a martial arts instructor, so he has an attractive, fit frame. He’s probably about 5’8″ with a smooth, medium tan skin tone that compliments his toned physique. He has an attractive, inviting face, the highlights of which are warm, almond-shaped, brown eyes and a sexy, short beard.
A bit of backstory: my husband and I are unofficially separated and getting divorced as soon as finances permit. We are not currently living together. I live in an apartment with roommates.
We had never met before he visited my apartment a couple days ago, the friend of my roommate’s boyfriend. The roommates and I were having dinner as a group and drinking/doing shots when he entered through the front door along with my roommate’s boyfriend. He made a round to introduce himself with a firm handshake and confident air about him. The evening progressed as we all sat around our living room, drinking and talking and laughing. I was fairly buzzed and becoming quite lively and animated. Through my buzzed haziness, I noticed Drew consistently making eye contact with me and I could tell he found me to be at least amusing (and, if I do say so myself, I become charmingly vivacious when drunk). He had mentioned a couple of times, however, the name of what I assumed to be his girlfriend, so I didn’t think much of it.
Once everyone had finished eating and all but one of us was fairly tipsy, we made a spur-of-the-moment decision to drive to the beach (the one of us who had not been drinking was the one who drove) at what was now about 1:00am. Drew and my roommate’s boyfriend decided to stay behind. Once we had finished at the beach and returned to the apartment soaked in seawater, covered in sand, and thoroughly intoxicated, I made a trip to the bathroom to go pee. As best I can recall, I stripped off my floor-length dress in the bathroom as well, as it was sopping wet and sandy. Underneath, I was wearing a pink thong and a white, see-through bra. While in the bathroom, I realized I didn’t know where my phone was and this sent me into a panic. I exited the bathroom, in just my undergarments, roaming frantically around the apartment, searching for my phone. One of my more sober roommates eventually found it, but not before Drew – who had been at the apartment drinking while we had been gone – had decided he liked my ass in that thong too much not to touch it a couple of times and squeeze it a few more as I walked around the house in search mode, barely clothed. Once I had my phone safely in my hands again and everyone else had retreated to their respective bedrooms, Drew and I were in the hall alone. He approached me, reached around to grab my ass again, and we began making out in the hall. In my drunken haze, I remembered that I thought he had mentioned a girlfriend, so I pulled away for a second and asked “Don’t you have a girlfriend?” He said, “Yeah. And I heard you have a husband.” All I said was, “Yes, I suppose so” before I pulled him back in to continue kissing.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We both realized things were getting too hot and heavy to keep it in the hallway, so we stumbled into my bedroom and shut the door. Drew, a very good kisser, pushed me against my bedroom wall and continued to lavish my mouth, neck, and collarbone with kisses as he pulled my thong to the side and began to rub my clit with his thumb as he inserted two fingers into my pussy. I. Was. Dripping. And I wanted him so badly. To my delight, he turned me with my back facing my bed and began to lay me down on top of my bedspread as he leaned down over me, went in to kiss my mouth several more times, then began to work his way down my chest and stomach. He then spread my legs wide and kneeled on my floor. He began to finger me again as he licked my clit, causing the pace of my breathing to pick up and the rest of my body to squirm. Suddenly, Drew stood up and, as he began to leave my room and leave me completely frustrated, said something about how he had to go but would be back later.
He left for the night. I was confused. I thought for certain I tasted too much like ocean water and that’s what had turned him off. The next morning, he had texted (at some point during our drunken interaction in the hallway, we had exchanged phone numbers) saying he was sorry if things had gotten weird and he hoped it hadn’t gone too far. I texted him saying I didn’t think it had to be weird unless we let it and asked him why he had left in such a hurry. He explained that at the point that he realized he was too intoxicated to get an erection, he decided to call it a night.
We proceeded to flirt over text that night and the next day. He then informed me he’d be over at the apartment to hang out with my roommate and her boyfriend later that evening. That evening, as I was returning home from my day and changing clothes in my room, I heard him leaving the apartment. After a moment of trepidation, I texted him “Leaving?” He said that he was going to, but he could come back and hang out if I wanted. Another moment of hesitancy (I had never, ever done anything like this before in my life – I’m that dumbass who married her first and had never had casual sex). And he had a girlfriend. But I did it. I said he should come back and hang out for a while.
I let him back in the front door, greeted him. He went to the kitchen and helped himself to his friend’s stash of beer, grabbing two for each of us. We made our way back to my room and opened our drinks. We awkwardly sat on my bed and made stilted small talk about I don’t even remember what. Things became more relaxed as we began to reminisce about the other night and how irresistibly sexy he had thought I looked when I came out of the bathroom in just my undies. For laughs, I showed him my closet-full of empty beer bottles, waiting to be recycled, and as I stood, pushing the closet door open, he approached me from behind and pushed himself against my back.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The moment he did this, I immediately wanted him again. I turned around, put my arms around his neck and we began to make out heavily. As we kissed and he ran his hands up and down my still-clothed body, squeezing my ass, caressing my breasts, feeling the curve of my waist, I reached down with one hand and began to rub his bulge over his jeans. He pulled away for a moment and excused himself to the bathroom. When he returned, I was sitting on the bed again. He sat and we took a break for a bit and began watching a TV show on my computer (I thought it a bit odd at the time that he seemed to want to dial things back down).
It wasn’t long until I crawled across the bed and began kissing him again. I was soon on my back with him crouching over me, kissing me deeply. He put his arms around me and lifted the top half of me off the bed, reached up my shirt and unclasped my bra, and pulled off the top half of my clothing. In one deft motion, he removed his own shirt as well, revealing his toned, tan, muscular torso. He then proceeded to almost frantically rip off my leggings and panties, unclasp his belt, and remove his own pants.
Both of us now fully naked, he leaned back over me, propping himself on his elbows and forearms, and began kissing me again. This time I could feel the smooth skin of his firm physique pressing against my breasts and his hard cock teasingly grazing my inner thighs. He, once again, began to work his way down my body, kissing my collar bone, my nipples, my stomach. Then he began fingering me and licking my clit until he had me writhing, moaning, and pressing my hands against the wall above my head. After three or four minutes of eating me out, he returned to my face and began to kiss me again.
We moved from laying horizontally to kneeling on the bed and I moved from stroking his cock while kissing his mouth to running my lips and hands over his chest and stomach. In honesty, I reluctantly slipped my mouth around his uncut cock, expecting it to be similar to the only other cock I had ever sucked (fishy oder and salty to the taste). To my surprise and delight, he was nearly odorless and tasteless. Due to this fact, with renewed enthusiasm, I held and stroked the base of his shaft with my hand while moving my mouth over the other half of his shaft and head, licking his tip with my tongue. At one point, he did put his hands on the back of my head and tried to go deeper into my throat, but stopped when he heard the small gagging noise I made.
After a while, he gently pulled me up to kiss me again and lean me backwards to lay on my back. As he did so, I asked if he had a condom (maybe a bit late, I know). He said yes and proceeded to take it out and put it on while making a joke that my roommate’s boyfriend had given it to him and it was very small. He then leaned back over me and entered me.
We fucked for a while in standard missionary with my legs wrapped around his waist, then he grabbed my ankles and put them over his shoulders, leaning down to suck my nipples every once in a while, the whole time rubbing my clit with his fingers. Next, he pulled me up onto me knees, turned me around, and bent me over.
I love taking it from behind, but I quickly realized he was a bit longer than I was used to and I could feel him hitting my cervix, which was not enjoyable. I continued to let him fuck me bent over, moving my hips around a bit to see if I could find an angle at which he didn’t keep hitting my cervix, but I couldn’t. If it weren’t for that discomfort, I would have thoroughly enjoyed him holding my hips while he fucked me, then leaning over my back to use one hand to play with my clit and the other to grab my hair and pull my head back. I would say it was at this point that I “lost” my orgasm because of the discomfort of all the cervix-hitting and I know I probably should have found a way to communicate that I wanted to switch positions.
Eventually we did change positions as he flipped me around, back into missionary, but this time he crouched over me, his chest pressed against my breasts. I wrapped my arms around his shoulders and upper back and felt both his sweet-smelling sweat and my orgasm beginning to build up.
He suddenly got up onto his knees, so I did too. He pulled me in to kiss me a bit, then turned me around, kneeling behind me so that we were both on our knees, facing the same direction, his chest and stomach against my back. I reached between my legs and guided his cock back into me. He began to fuck me hard and fast, reaching around to rub my clit with one hand and play with my breasts with his other hand, all the while kissing the back of my neck and shoulders. After a minute or so of this, he pulled out and lay down on his back.
I was disoriented for a brief second, as he had seemed to want to be the one in control of our fuck session until that point. But I regained composure and kneeled between his legs and began to suck his still-hard cock again. He indicated by gently pulling me away that I should stop and, I assumed, do something else. So I straddled him and inserted his still-erect cock back into me and began to ride him, moving my hips up and down slowly.
After just a few seconds, he said he “had to take a break,” so I got off of him and he got up and began to search for his boxer shorts, which neither of us could find at first. I told him he should turn the light back on, so he did and as we searched for his underwear, I saw his cock start to slowly become soft again, still inside the condom. I was fairly confused and was trying to figure out what had just happened as he found his boxers, put them on, and excused himself to the bathroom. While he was in the bathroom, panic struck as I put my red lace panties and a tee shirt back on and realized it was possible he had lost his erection, as I could decipher no point at which it distinctly seemed like he had cum. I became preemptively embarrassed and self-conscious and almost wanted to slink under the bed at this realization. I began to think maybe he had hated the view of me riding him so much that he became completely turned off and lost his hard-on. He came back into my bedroom with a smile on his face, though, and halfway sheepishly said, “I don’t usually finish that fast. I’m sure you’ve heard that before though.” I was immediately relieved. I smiled and giggled a bit. The thought did cross my mind that perhaps he had just decided it was better to say he had cum quickly than to acknowledge that he had lost his erection. I decided it was more likely and better for my ego to go ahead and believe him though.
He put his shirt back on, sat next to me and put his legs up on my bed. Not entirely sure how these hookup things go, I asked if he wanted to continue watching the show we had been watching before. He said sure, so we sat for a while watching in awkward silence. Then he began to chit chat about different things like school and work, asking me some getting-to-know-you questions. Still feeling the slight awkwardness, I offered in the politest way possible and with an understanding smile on my face that he didn’t have to stay if he didn’t want to and that I would understand if he had to go. He replied, smiling, that he wanted to stay and hang out a while unless I wanted him to go. I said of course I didn’t and I genuinely didn’t.
After a while of sitting with a couple feet of space between us on the bed, watching the show and intermittently chatting about personal stuff as well as the plot of the show, he reached his hand over and pulled on my arm. I thought he was trying to hold my hand, which would have felt strange to me, so I smiled uncertainly at him and asked what he was doing. He grinned and asked, “What? Am I not allowed to touch you anymore?” I said of course he could touch me still. He pulled on my arm again and said “Come over here.” To my complete and utter delight, he pulled me close to his side, wrapped one arm around my waist, and indicated that I should put my head on his shoulder. I did so gladly and we began to totally ignore the TV show and just talk very intimately about everything from favorite movies to number of sex partners to problems in our relationships. We laughed quite a bit and, as it turned out, we actually clicked on a personal level. A couple of times throughout our chatting, he turned his head toward mine and kissed me.
After probably an hour of cuddling and chatting away, he finally said he should go (it was around 1:00am). I walked him out to my apartment’s front porch and before he went, he put his arms around my waist and we began to make out again. He ran his hands along all my curves, but then pulled away, holding me by the waist still, looked at my face briefly, and said he’d see me soon and he’d text me.
I walked back into my apartment, barely able to wrap my head around what we had just done. Nevertheless, I had the hugest grin across my face.
Sure enough, he’s been texting over the last couple of days since our hookup. He just now informed me that next time he’s going to have me over to his place because his bed doesn’t squeak like mine and we won’t have to worry about people hearing us through paper-thin walls.
Did you have an orgasm? Did your partner(s)? I never orgasmed, but I didn’t really expect to be able to relax and get in the zone enough on the first time around with someone. I expect to have to wait until I’m more comfortable with him. Apparently he did orgasm, despite my initial worry that he had not. I still have not figured out exactly when he did, though, and have resolved to ask him next time to give me some sort of indication that he’s cumming or something. My best guess is that he came right before he laid down on his back, though he didn’t give any indication, verbal or otherwise, that he had finished.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom, though not for oral, which we probably should have. We did not discuss STI history.
What were your REASONS for having this hookup? I was horny, thought he was very cute, and, honestly, wanted to have more than one under my belt before I am jettisoned back into the dating world after my divorce. I assume from our chat about relationships that his reasons were mainly that he, I think, probably isn’t getting much attention from his girlfriend sexually and needed some release. According to him, he also couldn’t stop thinking about ripping my clothes off after seeing me running around my apartment nearly naked.
Were alcohol or drugs involved? If so, how much? During our first encounter in which he just ate me out for a minute, we were both drunk and he later told me he had also done some coke with my roommate’s boyfriend (another reason he couldn’t get it up that night). The next night when we actually hooked up, I had had a beer and a half and he had had two. He said it was the first time he had ever slept with someone he just met while sober.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We’ve been texting in the couple days since it happened. I think about it fondly several times a day and it always puts a smile on my face, particularly the cuddling afterward. He’s not someone I would ever, ever date since he apparently does hard drugs occasionally, but I think dating is the last thing on either of our minds. I’m sure we will hook up a couple more times at least, as he is around the apartment sometimes to hang out with my roommate and her boyfriend. He’s a cool guy and I find him very physically attractive.
To whom did you talk about the hookup? How did they react? I haven’t told anyone yet, though my roommate and her boyfriend know because her boyfriend loaned Drew a condom and I’m certain they could hear us through the wall.
Was this a consensual and/or wanted experience for you? For your partner? Totally consensual, and very much wanted on both our parts.
Do you regret this hookup? If so, why? If I had to give a yes or a no, I’d say no. There is a slight twinge of guilt because of his relationship situation, but not really because of mine, since mine is over.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not to be a complete girl about it, but the best thing for me was the cuddling and talking afterward. It was totally unexpected and it seemed like he really enjoyed it as well. The worst thing was the sense of embarrassed panic when I thought he might have lost his erection. This hookup has put a spring in my step and confidence in my demeanor in the couple of days since it’s happened and has made me feel very attractive and desirable.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
Anything else you want to add about this hookup or anything else? My biggest fear about this whole thing is having to meet and be around his girlfriend tonight at my roommate’s birthday party. We’re going bar hopping though, so alcohol will be my friend as far as that goes.
You have a hookup story to share? Submit it here!
What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!