Current location: Northeast – USA
Highest education received: College degree (eg., BA, BS)
Occupation: IT Professional
Relationship status: Married
Religious affiliation: Unaffiliated
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12-15
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 15 years
How would you best classify this hookup? Affair
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? Barbara was a co-worker in her early thirties that worked on the same floor as I did. She was quiet with a nice smile, Filipino, single mother with a couple of kids. A sales guy was getting on my case probably because he was having a bad day and just would not calm down. I finally had enough, came out of the office where I was sitting and was six steps or so from bitch slapping him in real-time. I had it timed with my steps so I could just walk into it, when over his shoulder Barb caught my eye. I walked past the sales guy over to her and asked “You got a minute?” She immediately grabbed her car keys and drove me around until I calmed down.
We had lunch while out and I got a chance to get to know more about her. I found out how smart she was because she was very talkative with me. We were just comfortable with each other and it showed. There was lots of laughing and endless conversation. Other than being Filipino there was nothing special about her and I don’t consider myself to be anything other than a plain guy.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I don’t remember how it actually began but, I setup an email account to communicate with Barb away from work. It became very suggestive quickly. It was probably me since I had a fantasy to get with an Asian woman, Pacific Island girl for as long as I could remember. Most likely something hanging around from my days of watching Hawaii Five-0 or Gilligan’s Island in childhood. I don’t think I was looking for some exotic, erotic experience but this was definitely as close I could get. Sex with Barbara was unbelievable.
The first time was a little uneasy as I was very nervous about being with another woman for the first time in ten years since I was married, but it escalated from there. The woman was multi-orgasmic like I could not believe. I gave her oral, rubbed her clit and fingered her and she would orgasm every couple of minutes while I was working on her. Her vagina was as tight as I ever felt even after two kids. She had small breasts that I loved to play with and just sucking on her nipples would send her into a body trembling orgasm.
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? She was quiet during sex with the occasional moan or dirty phrase. In the beginning I could not tell when she was cumming because she was so quiet but her orgasms were physical rather than verbal. She would squeeze, grab, clinch, shake, tremble or twist when she was having an orgasm. She would only get verbal when she was riding me (not my favorite position) and I would grab her ass. It was really clear that
she liked me to have a handful of her ass (it didn’t even take two hands). She liked being on top so much that she would lie on top of me during my recovery periods and pretend to be riding me while I would watch the news or a game show or something. Without actually grinding on me, more of an air-humping thing, Barb would roll off an orgasm every couple minutes or so. I could not believe that shit the first time she did it because she didn’t say anything. Her breathing would get heavy and the trembling of Barb cumming would follow. I looked on in amazement, disbelief or something because I wasn’t doing any touching and she didn’t masturbate at that point. I thought that she was faking but the juices were running off of her pussy and onto me. That would go on for 10-20 minutes. Let me tell you, it does a male ego good to have a naked woman on top of you and have multiple orgasms without you doing anything. I started to refer to myself in the third person and give myself nick names and stupid shit like that. The sex between Barb and myself was so exuberant that it was never a letdown when we got together.
We would go at it with oral, anal, vaginal, period sex, manual and every position we could get our bodies into. It was missionary, doggie, on our sides, her on her stomach, tables, chairs, window sills, against the wall, standing or on the floor. It was endless. We were fucking one day and Barb said she wanted me to cum on her. I wasn’t going to say no and she knew I was right there so, I pulled out and did what she asked. I must have blacked out or lost my balance or something because there was cum everywhere. It was on her breasts, face, in her hair, on the side table and on the wall. She was too busy rubbing it over her nipples and getting off to notice. Another day fucking would have me pull out and cum in her mouth. This opened an entire new pathway to pleasure for me because from that point she could not wait to get my dick in her mouth. If we couldn’t get somewhere to fuck she was more than happy to blow me until I came in her mouth. And she kept getting better at sucking me off.
One day after one of our intense meeting involving a lot of sex, I announced that I was “done” for the day. I really thought I was since my dick was actually hurting from being erect for hours and stroking Barbara’s tight pussy during the session. I got out of bed headed to the shower when Barb took hold of my hand while she knelt on the bed and began to work her magic on me. The passionate kisses, licking, nibbling and sucking, had me hard again even with a painful dick. She looked at me standing there with a hard-on again and the smirk on her face clearly said “Sorry, did you say something?”
Somewhere between the smug look on her face and me pushing her onto all fours and burying my dick into her, I decided that I was going to try and break her pussy. Put it out of commission for a few days maybe a week. Make it hurt like my dick. I had to do something because she had taken control and had my pride, as well as my balls in her hands.
I went to work doggie style hitting it as hard as I could but it wasn’t having the effect I was hoping for because Barbara was having orgasms as usual. I flipped her over, pushed her legs onto her breasts, entered her and went back to work jackhammer style. I was really trying to do some damage but it just wasn’t working. Barb had grabbed my shoulders, pushed her knees as wide as they could go with her elbows and was looking at my dick jackhammer her pussy like she was watching a movie. It was pelvis to pelvis as hard as I could but who can keep up the pace after 2 or 3 minutes. I had to slow to a pile driver pace, slow and very hard trying to put her ass thru the mattress and box spring. She had a hand on my hip guiding me to the timing of the strokes she wanted (this isn’t how it was supposed to happen). I had about a minute left in me and I gave it my all but it got really painful. I looked at Barb and her eyes were shut tight, mouth was open and she had both hands on my shoulders as she went into the most intense orgasm I had seen. Unfortunately she had a fistful of my shoulder in each hand and it seemed like it was being torn off my body.
I had nothing left in me to ejaculate so when she finished I collapsed beside her face first into the pillow gasping for air. I was really hoping that someone heard the commotion and called Fire and Rescue because I needed a paramedic with oxygen and a painkiller for my dick. I rolled over and looked at Barbara. Her hair was partially covering her face, had a lazy smile and her dreamy eyes looked at me as she took possession of the remaining control and pride that I had, as well as what was left of my soul when she said, “Now, you’re done”. That is really not how I envisioned it.
Barbara must have had some real pinned up sexual frustrations because nothing was off limits. It was clear that with me she was willing to try anything once then decide if it would go into the rotation of activities we would participate in but, she reached a line that I could not cross. I am OK with a little light bondage play and will smack a woman’s ass when in doggie style but that’s as far as I will go. I’m really not into inflicting pain.
Did you have an orgasm? Did your partner(s)? Could not count if I tried.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We talked about it. I had a vasectomy before I met her and had been faithful with marriage until this. She lived with some guy but would tell me when she had to “share” as she said. He would have to beg and badger her for days or weeks to get in between her legs. He needed condoms and lube to get any. For me, Barb could not wait and would blow me or have me finger her while I was driving and we never used a condom.
What were your REASONS for having this hookup? I think we both needed it. I know I needed the unfiltered passion. From the kissing to the orgasms. There wasn’t any thinking about it, no questions, just instinct and passion.
Were alcohol or drugs involved? If so, how much? No.
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? It went on for about 18 months or so before it ended. Barbara was always open to try anything with me and I would hear her say “I never…” after we would try something. You know, “I never let a guy have anal with me”, I never let a guy come in my mouth” type of comments. One day after a couple of rounds, she made one of the “I never…” statements. She would get wet from a couple of sentences in an email from me or a flashback of one of our sex sessions and had taken up masturbation to relieve her tension. She could not wait to show me. Pants off, on the bed, legs wide and going to town before I could get my shoes off. When she took a break she said “I never thought I would do that in front of a guy.” I asked her why did she was so open to doing all these “I never…” things with me. She looked at me then looked away. The room went silent. Not just quiet but one of those movie silences before something crashes through the wall or jumps out the dark corner to eat your ass. When she turned back to me I could see the tears in her eyes and running down her cheeks. We knew we were in trouble. An emotional connection wasn’t something we ever discussed but the cat was out the bag. She wanted and needed the things you did with a boyfriend, dinners, PDAs, trips together etc. the things that I could not do for her. We wound it down a couple months later after she found a new boyfriend. We lost touch after a while and I haven’t attempted to find her even though I know enough specific information that would make it easy.
To whom did you talk about the hookup? How did they react? Just this post.
Was this a consensual and/or wanted experience for you? For your partner? Very consensual.
Do you regret this hookup? If so, why? I don’t regret it but did not like the emotional wall we hit at the end of it. While she was all in during the time we were seeing each other, she didn’t need to get hurt near the end. It caught both of us by surprise.
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? The sex was the best. It was wide open passion and lust with only my boundaries in the way. I don’t think you can have that many orgasms together and not have an emotional bond happen. Once it’s in the open you can’t hide or make it go away. That’s the worst of it all.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative