Adult Confessions

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Did your date bring along an ex to your dinner? Was your date required to blow into a breathalyzer to start their vehicle? Did your date ask if you were in a "serious relationship" in under 15 minutes of meeting them? Did you hit the friends zone, without even taking the field? Did she have a machete hidden in her purse? Was your date fresh out of prison for murder? This is our category for confessing your real life cringe worthy dating disasters.

- Dating Disasters -
Straight Female / 28

Wish It Never Happened

My husband and I had a threesome with a guy I'd fancied so much. In fact I'd had a serious crush on him since high school.
During the sex in our home both men had me sucking their cocks and both took turns fucking me vaginally and anally.
At one point my husband and I were in a sixty nine with me on top taking our guests cock anally from behind.
He kept sliding his cock out and I could hear rather than see my husband sucking his dick.

After the sex we all had a drink together, then because of work the following morning I went to bed.
About an hour later I could hear muffled sounds of sex and got up thinking they were watching something.
I walked into the lounge without them seeing me and I witnessed my husband on his knees on our rug taking my crushes cock up his arsehole, and my husband was loving it saying "Yeh, fuck me, fuck me".

It's been four months since that night and I now live alone.
My husband now lives with **** in a cottage thirty miles away.
They began a gay relationship that night and now my husband wants a divorce.
I know for certain it was my husband's first time with a guy. And it was through my own insistence I enjoy my school crush, that we're no longer together.

Be careful what you wish for, because like me it might just leave you an incredibly hurt and lonely person.

3
# 78987 - by Amy / May 13, 2025
    • - Dating Disasters -
    Straight Female / 18

    Unexpected Threesome Gone Bad

    A few weeks ago me, my boyfriend and my sister were in my room horsing around and we started having sex in front of my sister. She got pissed saying it wasn’t fair us doing it in front of her so I asked her if she wanted to join. I thought she would say no because she had never done anything but she jumped at the chance. It was actually very exciting watching him do my sister for her first time and she definitely enjoyed it . Problem is she enjoyed it a little too much and she got pregnant. Now she doesn’t want to get a abortion which is causing problems for me and my boyfriend.

    5
    # 78986 - by Lydia / May 13, 2025
    - Dating Disasters -
    Straight Female / 39

    Treated Like A High Schooler

    I'm 39, I went on a date, and woke up fingered, fucked in the ass, with a hickey on my neck and on my chest.

    3
    # 78721 - by Susan / April 29, 2025
    • - Dating Disasters -
    Straight Female / 18

    A Decision I’m Dreading

    I’m 18 and will be graduating from high school in a few weeks. I have been accepted to college with plans to start in August.
    I recently went on spring break as I have for the last couple of years. I’ve been sexually active since my freshman year always with the exception of one time using condoms.
    Both years while on break I slept with college guys I met. I have been exceptionally careful making sure they didn’t get close to me without a condom since it was casual one night stands. Early last week when my period was supposed to come I was late. I waited until yesterday being five days late with no signs I took a pregnancy test and I’m pregnant. I’m very pro-life so this is extremely traumatic. The decision I have to make is an abortion which goes against my beliefs or have the baby and delay college for a year. I have no idea who got me pregnant which complicates the decision meaning I’ll be a single mother. I’m sure my parents will be upset but know they will support me either way.

    7
    # 78518 - by Kenzie / April 21, 2025
    - Dating Disasters -
    Straight Female / 18

    Threesome Gone Wrong

    My boyfriend has been pressuring me too have a threesome for some time but I wasn’t comfortable with it.
    The middle of March he, my younger sister and I went to the beach for a weekend. I was a little upset when he asked me to see if she would be interested in doing it but finally agreed to talk to her. She was a virgin so I wasn’t sure what her reaction would be.
    Of course she was reluctant at first but after some discussion assuring her with me being involved I would make sure she was ok.
    I’m on the pill so we bought condoms for him to use with her.
    Things went well even though she was very nervous at first but we had a threesome both nights while at the beach.
    Earlier this week she told me she was late. Last night I gave her a pregnancy test and sure enough somehow she got pregnant even though we took every precaution to avoid that happening.
    I feel awful now that I gave into my boyfriend especially since it is my sister he knocked Up.
    We haven’t told him yet so I’m not sure how he’s going to feel.
    Our parents would be devastated if they found out so we are going to see what we need to do to get her an abortion.

    4
    # 78331 - by Leigh / April 13, 2025
    • - Dating Disasters -
    Straight Female / 25

    Just Explaining That Babies Are Not The End Of The World, Far From It

    As a 19 year old freshman student I got pregnant with an upper classman. The school had a campus clinic, but of course they don't issue day after medication. They had a place to send me, but it was too far and I didn't have a car. The bottom line is I never visited that center and I had to tell my 'friend' that he was going to be a father.

    I wasn't upset. I wasn't scared. Babies come and you take care of them. I have never been scared of babies. I went home and told my mother, who told my father, who announced it at the table. No one said much, other than make sure he can pay his share. The baby was welcome as soon as she was born and between my mother and sister I was able to stay in college.

    After the baby daddy got a real job he started paying his share, we never went after him for the three years until he graduated. Why? What was the purpose of tying him down before he could pay? My parents didn't have a problem paying for me and their new granddaughter. In our home, the more the merrier, all babies are welcome. It's not like I was the first one to come home with a baby.

    After I graduated I talked to him and suggested that we make it legal, for the sake of the baby, since the baby already needed a sibling. And I was of the mind to get all my birthing duties complete before I turned 25 and get it behind me.

    We made it, we have a home and he has a good job and I work part time. In part because my family chipped in when we needed. Not only for me, for another sister who found out where babies come from. We aren't rich, we aren't poor, we are right in the middle. And the truth of it all is that he is better off for having a wife and a couple of babies to look after and worry about when things go bump in the night.

    Kendra

    2
    # 78197 - by Kendra / April 8, 2025
    - Dating Disasters -
    Straight Male / 34

    Be Careful

    We have been into swinging for about two years. Made a big mistake and it can't be taken back.
    We have been seeing a steady male. A black guy named Daniel. Wife even referred to him as her "boyfriend".
    A month ago Daniel asked my wife to come to his house and spend the weekend solo. We talked about it and she accepted the invitation. Plan was for me to drop her off Friday evening around 6pm. Pick her up Sunday around noon.
    She called me Saturday evening and I picked her up at a convenience store near Daniels home. She was nearly doubled over with stomach pain. I took her to the ER. She wouldn't tell me what happened. Still hasn't. I looked at the discharge paperwork. Noted was severe internal bruising to her uterus, plus vaginal and anal tearing.
    I tried calling Daniel. He didn't answer but he did text me back. He said "we had a great time with her, wanna see the video".
    We haven't had sex and she won't tell me what happened.

    8
    # 78136 - by Husband / April 6, 2025
    - Dating Disasters -
    Gender Neutral / 66

    Being Of Short Stature

    I thought being an older person Height would np longer be an issue m but it still is, when asking a woman out who is around your own age and being more or less rejected because of it is a bit disheartening, I have an opportunity to meet many women at the Gym I frequent so far no luck perhaps a few are widows and not looking to date so will keep looking

    4
    # 78106 - by Athensgold124 / April 4, 2025
    - Dating Disasters -
    Straight Female / 20

    The Party After The Rehearsal Dinner Party

    Another huge wedding. Moms getting remarried. Let's get everything planned out and sending those invites. Get to meet my new family members because some of them live elsewhere. John my future stepfather has two grown kids. John Jr, 22 Cindy 20. Finally, the events where planned. This rehearsal party will never be forgotten. About fifteen of us meant up at the local sports bar. And we partied it up. I ended up going to the local motel 6 with my future stepbrother and receiving two loads of baby makers. Bad news one little baby maker hit the spot. Ops. And now I'm planning a family event to share the news.

    3
    # 77970 - by Katie / March 31, 2025
    • - Dating Disasters -
    Straight Male / 45

    My First Time

    We were late teens (19-ish), just out of school. Both virgins who had only met a few days ago randomly on the bus. She was a bigger girl—actually cute—but had some body image and self-esteem issues. She also had a great rack I could have played with all day long. I was average or just a bit over, but super shy and socially awkward. She thought I was maybe the catch of a lifetime, but I was so shy that if she hadn't hit on me, it never would have happened.

    We had no friends in common, and she'd just been hanging at my place—making out, stroking me, and letting me play with her huge tits. The only thing that pissed me off was that she refused oral, both giving and receiving. I don't know why. Since it was summer and no one was home, and we both didn’t have a lot of friends, I dry-humped her, fondled her, and got jacked off for almost two days straight but was too shy to ask to fuck her.

    Finally, at the end of the second day, she was like, "Buy some condoms before I come over tomorrow," and I thought I was gonna die of shock. But you bet I did, and I had them in the open when she got there.

    It was painful for her and just okay for me. Mish. I banged her good—I had seen enough porn. I was finally in a real pussy, so I was gonna fuck it good. It was wet, felt great being in it, and since she was a virgin, it was hard getting in. But once I was in, she didn’t have as much grip as I thought. I pounded it as best as I could, but I couldn’t cum because she was hurting too much. While it felt good to me, she was near tears and totally suffered through it for me. I think this is where my sadist kink came from, lol.

    She kept telling me to keep going because she had a crush on me and wanted the sex to keep me. I felt bad, and not knowing what was wrong with her or why she was in so much pain, I worried I had really hurt her, so I stopped. That made her feel bad. Later (a few hours later), she got me off by letting me titty fuck her huge cans, and honestly, it was actually better than fucking her.

    I fucked her a few more times that summer. She used sex to keep me interested, but it backfired because she never got better at it or even wanted to enjoy it. Let me be clear—I was no better at it than her, but she kept throwing it at me, wanting me to fuck her. She just wanted me to get what I needed as a carrot to keep me, so she lay there like a dead fish and duty-fucked me. Bad sex didn’t bond us. I got off, but not by much.

    She came over less and less because I’d just fuck her, and we had nothing to talk about. The last time she came over, she didn’t want to fuck (likely on her period), and it was so awkward. I was an ass and said something like, "Maybe you shouldn’t come back if you’re not gonna let me fuck. This is awkward."

    She, of course, was hurt, and I never saw her again.

    I feel bad. I was an ass, but we were kids. I hope she had better boyfriends than me after that. I think of her sometimes but can’t even recall her name, lol. Sorry, whoever you were.

    4
    # 77855 - by Marv / March 27, 2025
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