What a MISTAKE!!

by Tommber

What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Retiring Executive
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? The Man Who Loved Women (movie reference)
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 16

What a MISTAKE!!

How long ago did this hookup happen? July 2004

What was your relationship status at the time? Single

How would you best classify this hookup?

How long did you know the person before this hookup? For more than 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? E. was beautiful. She stood 5’8½” tall, weighed about 135 lbs., with slightly wavy brunette hair that she kept at shoulder length. She sported nicely set B-cup breasts, a fairly athletic looking ass supported by perfect hips in a 36”-24”-35” body.

E. and I had dated for a couple of years in a semi-open relationship in the early 1990’s (meaning that she knew I had other partners but she was reluctant to indulge herself, although she did one time; and she was surprised that I appreciated the pics she allowed him to take of her sucking his cock, and that I wanted her to tell me all about it). When we stopped seeing each other we parted on friendly terms to the point of me sleeping with her without sex many times after we stopped hooking up until I met the woman who would become my first wife. E. and I had developed what I thought was a real, lasting friendship, especially since she attended my first wedding (yes, my first wife did know about our history but said she was okay with us being friends still.)

Now, to bring this forward to the above mentioned time period. I had been away on a long term assignment for 4½ years, up until February 2004. E. knew that I had been divorced because she would occasionally call my mother and get updates on my situation (they were always chummy because they both loved crafts). Two weeks after my assignment ended, I called E., knowing that she was not aware that I was back in the country yet. I had a nickname for her that was based on her real name, but I was the only one she ever allowed to call her that. When she answered her phone I addressed her by her full name and, only after she asked who was calling did I use the nickname, saying, “E…, you really don’t recognize my voice?” She squealed in delight and said, “YOU’RE HOME?!? I KNOW you’re coming to see me!” I told her that I would love to see her again the next evening.

E. helped me get over my ex-wife, even being with me the day a couple months later when I took off my wedding band and threw it into the river together. Our relationship blossomed again over the next few months until I told her that I wanted to marry her the following year. We each had some issues we needed to tie up before making any real plans. The relationship, however, seemed to be in full swing again.

Fast forward to July of that year. E. and I did not see eye-to-eye politically. In fact, we sat at complete opposite ends of the spectrum, but we always had great emotional and sexual chemistry. Prior to the night of this hookup we had made out heavily a number of times, holding back our lust for each other, nearly to the point of pain at times. We had agreed to be exclusively for each other, and I loved E. and, like I said, was planning to marry her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was with E. at her apartment on a Friday evening. She prepared a nice dinner just for the two of us (her 15 year old son was with his dad for the weekend), and we sat down to watch a movie she rented from Blockbuster. We sat on the sofa, she leaning on me with my arm draped over her shoulders. At some point, less than a ½ hour into the movie, she moved in such a way that my hand landed naturally on her breast. (sidebar: one of E.’s most unique physical features was her left nipple; while she had slightly larger than average nipples, her left one looked almost as if it had been pinched with pliers so hard that it stayed sort of flattened out in a slightly diagonal orientation.) She then looked up and started kissing me. We had talked several times about what might happen if we decided to have intercourse again, which we were both very excited for.

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? After making out for about 10 minutes on the sofa, I got up, took her hands and led her into the bedroom. We continued making out standing up for a few minutes while I opened her blouse, and she undoing my trousers, then I backed her to the bed and laid her down, and proceeded to undo her jeans. After stripping her down completely I laid down halfway on top of her with my lower body off to her side, and played with her clitoris the way I remembered that she liked it more than a decade earlier. After several minutes of this I began kissing my way down her body, making sure to pay proper attention to her tits, especially the uniquely shaped left nipple, which was hyper sensitive. I then went down on her and ate her pussy for more than a ½ hour to countless, spasmodic orgasms until she pushed my head back and told me she couldn’t take it any more, than she needed time to catch her breath. I then slid up on top of her into the missionary position, and we made out with me stroking my extremely rigid cock against the outside of her supremely soaked vagina. I was super tempted to go ahead and just slide inside her but held back, even though our bodies were such that we had never once had to direct my penis into her, it just fit perfectly every time. After about 5 minutes or so of this E. asked me if I would like her to return the favor. I told her that she knew I loved how she gave head but that I didn’t require or even necessarily expect anything in return. With that she said, “I think I don’t want to feel like I owe you.” So, she went down on me and sucked my cock for better than 20 minutes, humming and being quite vocal before I told her that I was about to cum. She just kept the pace until I came in her mouth, and she didn’t let a single drop fall out. But, after more than 10 years, I had forgotten that she refused to swallow, so she got up, looked at me, put her hand over her mouth and mumbled, “Mmm. Gmmph.” and put up a finger before she pretty much ran to the bathroom to spit it into the sink.

We made out for a little bit longer when she came back to the bed, then laid there while I cuddled her for maybe 10 minutes before she said with a put-on smile and fake concern, “I think it’s probably about time you get home. You do have to work early in the morning.”

How sexually satisfying was this hookup? A little

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? Physically I felt pretty good after being with E. that night. But oddly I felt mentally disjointed and emotionally disconnected from her. I think part of that was because she didn’t remind me ahead of time that she didn’t swallow but instead hollered it back to me from the bathroom after spitting out my cum, and then (even more of the reason) the final little bit of making out felt almost as if I was kissing a hooker while being unaware of her being one, i.e., her just going through the motions with no emotion or desire. I was rather disappointed that she turned from this hot, passionate lover to what seemed like more of a cold, heartless hooker in less than 20 minutes.

I found out the next day why the switch in her demeanor when I called her after I got out of work. She said something to the effect of, “It wouldn’t be a good thing for you to come around anymore.” Of course, I asked what was the problem. Then she dropped the bomb that blasted me three states away. She told me that she had met another guy and was getting married in two weeks. Of course, I was very upset and asked her how this could happen. She asked me if I remembered meeting the guy who sat behind us in church a couple weeks earlier. Yes, I remembered him; he seemed to be a nice guy. Well, even knowing that we were there together, he had asked her for her number, and then they went out that same night and, the rest as they say, is history. I felt betrayed, cheated, lied to, and used (not only for sex but more as some sort of patsy). I verbally blasted her and told her that it wouldn’t work, that they would be divorced inside 2 years because she had no sense of commitment (she had been married and divorced four other times already), and that they both did and did not deserve each other.

She told me that she’d had that night planned for the past week. I told her that I should have fucked her like the bitch she was. Then I hung up and never tried to contact her again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Never talked to anybody about it. I think that kind of situation one should keep to themselves because the only reason to talk about it, at least back then, would have been to trash her. I’ve never been one to intentionally talk negatively about another person.

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

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Very much

Why do you regret this hookup? Several reasons. She lied to me; betrayed my trust on many levels; and switched from this sweet, sexy, loving lady to a cold-hearted b…. almost at the blink of an eye.

I wish I had gone ahead and fucked her. But, then again, I probably would have regretted that just as much. At least this way I don’t regret my behavior that night.

What was the BEST thing about this hookup? Eating her to countless orgasms until she had to ask for a break to catch her breath.

What was the WORST thing about this hookup? Her dishonesty and betrayal, which led what should have been a really sweet afterglow to being probably the worst after sex experience I’ve ever had.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? After that night I grew kind of calloused toward women for a little while. After thinking about it, and about how this could affect my behavior going forward, I realized that it was not my right nor responsibility to hate her, or anybody else for that matter. I looked back over my life and remembered some of the women that I had hurt emotionally in various ways and for various reasons, then just told myself, “Don’t judge her. Put yourself in her shoes. If you were her, with the same exact set of life experiences, you would have done exactly as she did. You are no better or worse than she is; just different. Let it go.”

So I did just that. After going through that experience I decided to judge others less and to just take heed to my own thoughts and behaviors. It just makes sense to me to be less critical.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Very negative

Anything else you want to add about this hookup? Although I said some very harsh things, and meant them, deep down inside I really wished the best for her. That being said, I should have fucked (er, made love to) her. I didn’t realize going into that evening that it was going to be casual sex. I guess I was the sucker.

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? Look at some of my other posts.

What do you think about the Casual Sex Project? Enjoy reading the thoughts and feelings of others.

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