What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US – Iowa
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 7
Hook-up With Married Co-worker
How long ago did this hookup happen? 12 years ago
What was your relationship status at the time? In a relationship (monogamous)
How would you best classify this hookup? Short fling
How long did you know the person before this hookup? For 1 to 3 years
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? Maria was a mid-30s part-latino woman who worked as a third party service provider for the company I worked for in Minnesota. She was probably around 5′ or so and had a few extra pounds from a couple of children, but otherwise a proportional build for her height. She had beautiful curly hair and eyes that were very striking. I had met her when I started at this company at 23 years old, and we quickly developed a casual, sometimes flirty relationship, in the office. After about a year and a half, I took a promotion at another location in Iowa, and we exchanged numbers to keep in contact.
At the time, I was dating my girlfriend, who I had also met at my work. She and I were monogamous at the time and had great sex, but now we were 3 hours apart and saw each other maybe every other weekend. Maria and I started texting each other, initially platonically, a couple of times a week, but soon daily and with deeper discussions. Maria told me about her marriage and how her husband (he was in his 50s) was strict and both verbally and emotionally abusive to her. She also said that they rarely had sex and that she couldn’t broach the subject with him since he wouldn’t listen to her needs. She is also envious of me being young and having lots of sex and that she misses that part of her life. She said she has never cheated on her husband, but was at a point where she wanted to please a man who actually cared about her, even if it was just sexual in nature.
Me, being the hormone-rampant 20-something at the time, was excited to hear this and said that I thought she was very attractive and that she would have no problem finding someone to give her the sex she needed. She said that I would be a good fit and that it’s too bad I was in a relationship at the time or else she would love to hook-up with me. At the time, I had a lot more guilt about cheating, but I said that I have never been with an older woman, and I bet she could show me some things. I remember us sharing some naked pics through our phone, and she showed me both her large breasts with dark, large aureolas and prominent nipples, as well as her tight curly haired pubes glistening above her protruding labia.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a few weeks of our sexting and regular conversation, she told me that she was planning to drive down to Missouri to stay with her sister that Friday, and she wanted sex. We arranged for her to stop by my apartment to hang out and hook-up, as the town I was in was directly on her drive down. Now, that Friday I was also supposed to be back up in Minnesota to visit my GF, as I had taken the day off from work. So, I was nervous about lying and cheating on my GF, but I also was way into having sex with Maria.
Maria showed up at my apartment in the early afternoon, and I greeted her at her car (a new retro-styled red Mustang GT) with a big hug. We go into my apartment and have small talk along the way, saying that it was great to see each other again and how we both were horny. As soon as she put her bag down, she turned to me, looked up, and kissed me on the lips. We made out and stumbled back to the bedroom.
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? In the bedroom, we started stripping off our clothes while making out. I was finally down to just my shorts, while she had removed hers, but kept her top on. She undid my belt and shorts, and they fell to the floor. We were giggling and laughing, as she hadn’t been with another man since she was married, so for at least 12 years. She grabbed a hold of my erection in my boxer briefs and proceeded to get down on her knees. She pulled off my underwear, and my 6″ cut cock popped out in front of her face. She grabbed a hold of it with one hand, looked up at me, and opened her mouth. She started sucking on my large cock head. I moaned in ecstasy as she sucked on my cock and rubbed my shaft. She explained before how she was naive about sex and wanted guidance from me, so I told her she was doing good, and to pay attention to my balls with her hand and continue licking. She sucked me for a couple of minutes until I got to the point where I wanted to taste her pussy.
I helped her stand up, and now that she was hornier from sucking my cock, she took off her blouse and bra. We climbed onto the bed, kissing a bit, and I had her lay down on her back. I rubbed up on her pussy over her underwear as we made out, and I proceed to pull them down as she spread her legs open, exposing her trimmed mound and wet labia. I slid a finger in her cleft, and she jumped a bit, moaning that it felt great. I leaned down to take a lick of her pussy and get only 3 laps of her sweet nectar before she pulled me up and said that she wanted to have sex (and that she wasn’t into getting oral). She had been sterilized after her kids and couldn’t get pregnant. She also said that she wanted to have unprotected sex, and since we both had only been in monogamous relationships, we would both be clean.
I lined up with her sweet hole and rubbed it on the outside before pushing the tip in. She was moving around quite a bit and screamed as she had her first orgasm. I slid the rest of the way in and laid on top of her, thrusting my hips and making out. We had sex like this for a couple of minutes before she said that she wanted to ride me. I switched spots with her, and she leaned down and started sucking my cock for a little bit before getting back on her knees. She climbed on top of me and slid my cock into her pussy. She leaned back and grabbed my legs with her hands pushing her hips into the air, giving me a show as I watched my cock sliding in and out of her dark pussy. I can see her moaning as we both start sweating from the workout. She started shaking every 30 seconds or so, having orgasms as she rides me.
We fuck like this for a couple more minutes, and I told her I was close. She said that she wanted to suck me off. She climbed off me and proceeded to take my very hard cock in her mouth sucking and stroking me. I told her I was going to cum, and she put her lips over my head and strokes me until I blast my load into her throat. At the time, I could blast some fairly big loads, and she proceeded to choke a bit as she swallowed my cum. I pulled her up to my face, gave her a kiss and we cuddle for a few minutes.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
Did your partner have an orgasm? Yes, multiple
What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We hung out for a few minutes and then got dressed. I walked her back to her car, so she could get on the road. The last time I saw Maria was when she was driving off in her red Mustang. At the time, I had a pang of guilt from cheating on my girlfriend, but the sex was amazing with Maria, and we said that maybe we could do it again sometime. I went back up to my apartment and packed my car and left for my girlfriend’s. I was worried about the sex smell on me and took a shower when I got to her apartment. We had sex that night, and I was imagining fucking Maria earlier in the day.
We kept texting for another year but never reconnected. I ended up breaking up with my girlfriend at the time as I wanted more sexual freedom.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Sterilization, Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel more desirable
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? Not at all (no alcohol or drugs)
How wanted was this hookup for you at the time? Very
Did you consent to this hookup at the time? I gave enthusiastic consent
How wanted was this hookup for your partner at the time? Very
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? Maybe a few friends know about it, but most do not.
How would you best summarize people’s reactions about this hookup? Relatively positive
Did you get emotionally hurt as a result of this hookup? Not at all
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It was great to have sex with someone I felt emotionally connected with, even if it was a one time thing.
What was the WORST thing about this hookup? Cheating on my then girlfriend; however, I’ve learned to embrace my sexuality and sexual needs.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
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