This post is sponsored by The T Bar.


What’s your gender? Woman
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA – California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status?
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? reawakened and loving it but frustrated
How many sexual partners have you had in your life (including oral sex)? 10ish
How many hookup stories have you here posted before? 0

Reawakened sexuality

How long ago did this hookup happen? August 2015

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? He was tall. Over 6′ and on the thinner side, but athletic. Balding, but very intense eyes. Dark hair. He was stunning when he was younger and some of that beauty was still there in his face despite the fact that he was now 58 and a little tired around the edges of his eyes. He rides his bike through the Oakland Hills every day so he’s strong. My friend Dennis refers to him as “Voldemort” for many funny reasons not relevant to this story so I’ll refer to him as V which is how we short hand it. V and I met on Ashley Madison. I know … it’s not something I’m proud of. But my husband of 18 years, with whom I had been in a very monogamous relationship for 24 years since I was 28 years old, had several years earlier gotten very sick. He suffered a big brain injury and was never the same. After a false start or two, being very confused about my role as the dutiful spouse and caretaker, I finally realized I needed something more. I needed a man and sex and someone to touch and talk to. V was one of the first men I met on AM. And he was incredible. We started emailed on the first day of a 10-day trip I took with my kids to Los Angeles and Santa Barbara. By the end of the 10 days I felt that I knew him better than anyone I had ever known. He was a beautiful writer. Had kids the same ages as mine. A wife who was also ill. We are both lawyers and understand each other’s work. He asked my opinion about his cases and strategy. He seemed to understand what I needed. We agreed to meet at a bar in the city where I live several days after I returned from my trip. That initial meeting only lasted a couple of hours but it was as if I had known him forever. At that point his emails turned sexual and he would email to tell me how hard he got at the mere thought of me during his day. I knew I would have him at some point and it was all I could think about. It didn’t matter that I hardly knew him. I just wanted him and I wanted to move on in my life from illness and hospitals and screaming mad brain damaged husbands. I wanted someone for me who would appreciate me and really enjoy me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After our initial meeting in the wine bar, V and I seemed to really hit it off. We agreed to have dinner a couple of days later which led to a romantic walk along the waterfront under the moon and making out under a beautiful bridge. Both of us were very lonely as it had been 2.5 years for me and 3 for him since either of us last had sex. We agreed to meet up several days later at a hotel in town. I couldn’t believe I had actually found someone I connected with on an emotional level, who seemed to really understand what I needed. And I was comfortable with him and could talk and be myself! The day of the rendezvous arrived. I had to go to another city for work several hours away that morning and was worried I would not make it back in time to meet him at the hotel as we planned at 1pm. I raced through my work. All the while he was sending me emails about how excited he was to meet up with me, how he had checked in, how he had ordered oysters and champagne and was there waiting … I was wet from the moment I got up, through my meetings that I could hardly focus on, on the drive all the way back to the city … it was incredible. I wore a pretty floral dress and high heels so I’d be taller to match his height.

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? I made it downtown, parked and ran over to the hotel. He gave me the room number. I went up and knocked on the door and there he was opening the door for me! The room was dark and peaceful. He had food out for us and gave me a glass of champagne. He talked a little about a big case he has and what was going on in the action. We sat down on the a bench at the end of the bed and talked and leaned back against the end of the bed. I was so nervous. He reached over at one point and kissed me and it was like all the tension and stress and anger at my husband and sadness just poured out. I kissed him back like I have never kissed anyone before. My leg involuntarily lifted up on its own and wrapped around him and pulled him closer. I could feel how hard he was through his suit pants. He pulled away laughing and said “oh we are going to be the best of friends!” before diving back in and very deftly unhooking my bra with one hand behind my back. We undressed each other and kissed naked for a while. I loved his chest which had full hair across the top and gradual nice fur down his belly. I had never been with a man with chest hair and I am a total convert now! V moaned as I stroked his chest and cock. I have always loved the feeling of a hard cock pressed up against my pussy while kissing. I can almost come from that alone. I have never come from intercourse. I love the feeling of a hard cock inside me pounding away, but it has never given me an orgasm. But that same cock pushing into my clit can send me over the edge. So we kissed and he went down on me which was just incredible since it had been a while. I was nervous even though I needed and wanted him so much, and I didn’t come unfortunately. He tried to wipe his mouth off on the sheets before kissing me, but I pulled him in for another long kiss since I love the taste of my own juices on a man while kissing him. Then the moment of truth! I took his cock and put it into my extremely wet pussy and that was it. I was an adulteress having sex with a man I had just met off Ashley Madison! It felt so incredibly good. His cock was smaller than average actually. I remember being surprised when I saw it. But he was as hard as granite and fit so well inside me. I was so wet it was no problem. We didn’t use condoms (which I sort of regret and as I have had more casual sex in this past year I realize how important it is, but he didn’t mention it and I didn’t insist so …. if my daughters ever do something like this I will scream at them!), but we talked about sexual history. Neither of us had had sex in so long, and then only with our respective spouses for years that I felt he was safe. I tend to love missionary but haven’t had a wild number of partners and am very open to trying different things. Sex with V was pretty vanilla however, but it still felt so good. My husband was a big guy, kind of overweight so having me on top was always difficult. But V flipped me over at one point with me on top and the rhythm of our movement just made sense. I have yet to experience intercourse that felt quite like it did with V. His size and body fit mine so well. After a while of alternating between missionary and me on top he came. The odd thing was he was silent. Completely silent when he came. I like some dirty talk. Some moaning. He moaned a little as we fucked, and he told me repeatedly “you can’t know how good this feels …” but he never made a peep when he came. Strange.

We took a break after that and ate some, talked some, and then went for round two. That just involved more intercourse but no more oral on me. I gave him oral for a while but he preferred intercourse. We were in that hotel room for SEVEN hours. Seven hours that flew by. I got my fill of talking and touching and sucking and licking … he wasn’t the best lover I ever had. But I needed it. I really needed to move on and leave the situation at home behind. But I have kids and responsibility and I had to gather myself and drive home. My teenager daughters can track me on my iphone and I had to have a good excuse as to why I had been downtown all day instead of in the city where I said I had to go for work that morning. V walked me downstairs while he went to the train and I went to the parking garage. He gave me a tiny hug since we were standing right in the middle of evening rush hour and he was worried one of our colleagues might walk by and see us smooching on the sidewalk. That was a little weird. I wasn’t prepared for the “married man” phenomenon. Sneakiness and feeling guilty that we had done something wrong. Only it wasn’t wrong! It was awesome.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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 went on to hook up three more times. We switched off organizing the meetings in different swank hotels around town. Each time was really frustrating for me, although it was so wonderful to see him, because it was only once a month. I wasn’t looking to fall in love and be in a big relationship with a married man. And at that time I didn’t know that I was headed for divorce myself, but I needed sex more than once a month. I continued to email V all the time but my needs overwhelmed our relationship and he started pulling away. When I finally did leave my husband and start divorce proceedings V recommended a lawyer for me. Someone who sits in his office! Ha ha ha. But we stopped seeing each other sexually. Frankly, V turned into a shit who ran away once my life started making more sense to me. He wanted to sneak around in fancy hotels once a month. He did not want me on a more full time basis. Now he still emails me from time to time, and we have lunch periodically. But there is no sex. We still have tons of sexual tension and I hate it that I can’t fuck him anymore. It makes me alternate between hating him and wanting him back in my life. I went on to have another relationship with another married man — a different story I may write about in the future — that was more of the same. Small doses. Me longing and wanting so much more. Me realizing married men suck and I need to stay far away from them. But no one has been as much my right match as V was. I can’t quit him!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To cheer myself up, I was feeling lonely

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? I told lots of different safe people in my life who know about my situation at home, didn’t judge me for looking for a physical and emotional connection elsewhere, and who were supportive of the decision. It felt really good to talk about it. I eventually told my therapist too who never tells me what she thinks!

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Very

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? V is an intense, emotional, smart, incredible guy. I needed him right at the time he came along. And he needed me. I don’t understand him, and I think he isn’t being honest with me. But he made me feel sexy and wanted, and he paved the way for leaving my husband and a very bad situation at home. I know that some day I will have a solid relationship again that gives me everything I need and want.

What was the WORST thing about this hookup? V doesn’t want it to continue. Not sure what that’s about. He calls me. He connects with me emotionally. But then he takes off when I start to get closer. He is a mystery and a bit sick of it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I had never had casual sex before in all the time I have been sexually active since college. I always was in relationships with men whom I loved. I thought you had to be in love to have fun with someone! I titled this story “reawakened” because it’s like my sexuality just woke up. After years with the same person — and in all honestly sex with my husband wasn’t all that – I just assumed that it was over for me. I loved my husband but did not want to fuck him. And when we did it was quick and over. Suddenly I realized I could walk around slippery wet for days at the mere thought of V and his cock and his touch and kissing him. I still feel that when I think of V. But I feel it at the thought of the cute butcher around the corner. And of the hook up I had after V … I love men and I want them in my life. I can’t just fuck someone once anonymously. I need to like and want them. But I don’t have to be in love to enjoy that. Such a revelation!

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? V is a good guy. A confused guy, but a good person. I will probably stay his friend and hope that we hook up again some day.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I want much more of the kind of sex I had with V and post V. Something between too serious and too casual. Having trouble finding that! Mid-50’s men out there who are available — where the fuck are you all?????

What do you think about the Casual Sex Project? It’s amazing. I don’t even remember how I found it but started reading it more or less regularly since I met V. It is fun. It makes me realize I’m not alone in how I feel about all of this. I’m not wild about the straight “here’s how we fucked” stories. Someone here — a man, a man I wish I could meet haha — said he likes the stories with emotion. I like that too. I want to know what motivated people and how they felt about it and why it was so good. Not really into the group stories but I read them anyway.

You have a hookup story to share? Submit it here!