Cheating With My Best Friend’s Boyfriend

by Kate

Gender: Female
Age: 18
Race/ethnicity: White
Current location: New England
Highest education received: Not graduated from high-school
Relationship status: In a relationship
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bi curious
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Cheating With My Best Friend’s Boyfriend

How long ago did this hookup happen? Last night

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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, probably about 6’4, 20 years old. Short dark brown hair, very muscular, a bit of baby fat but in a cute way. I know them pretty well, he is my best friends long term boyfriend. I also have a long term boyfriend. We had not hooked up before but I had tried to previously when I was drunk but him and his girlfriend were both sober and knew I was wasted so they wouldn’t let me. Before hooking up, I knew if the chance ever came up I would most likely sleep with them.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? So it really started at a party about an hour from where we live, we’ll call my friends Drew and Beth. Me and Beth are best friends, me her and Drew party together almost every weekend because I can’t with my boyfriend because he doesn’t want me drinking or smoking. Drew is usually the DD (Designated Driver) and he was that night. Me and Beth were both pretty drunk, but she was definitely more drunk. Drew is always trying to get me and her to make out when we’re drunk. I fell asleep in the backseat on the way home for a minute and I could hear a faint mumbling from the front seat. Then I heard drew say “so wake her up” and Beth woke me up and drew said “kate, Beth says she’ll make out with you if you want to” and I said something along the lines of “what Im too drunk for this guys” and the whole way home drew kept trying to get us to make out. Then we got home and all laid down on Beths twin bed, me on the inside, Beth in the middle and drew on the outside. Drew made Beth roll over towards me and tried to get us to kiss. Beth fell asleep and drew got in the middle. Drew was definitely instigating it.

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? We laid there for a few minutes with his back to me and beths back to drew. I was pretty drunk so I poked drews stomach and I was like “where’s your belly button?” And he said “lower, to the left” and I touched his bellybutton and started laughing my ass off. Then I lost his bellybutton and he said “a little bit lower” and I poked lower and poked his dick. He said “well hey there” and I said “hi drew!” And he said “well your hands already down there, you might as well” and I remember me and Beth had had a drunk conversation earlier about a three way. I said to drew “Beth will kill me” and he said “well she never said no” so I started giving him a hand job. He was really enjoying it and he was breathing fast and heavy and it was getting really hot. Beth was snoring this whole time so we knew she was alseep. Drew put his arm around me and started rubbing my back and my neck. He was saying things like “this is nice, you’re so good” and I said “why don’t you wake Beth up, it’ll be even nicer” so he tried to wake her up and she was completely passed out drunk. He said “so how good are you with your mouth?” And I giggled and shrugged, continuing to stroke his dick. He said “why don’t we find out?” He put his hand on the back of my head and lightly pushed down and I gladly went down on him. He reached down and played with my boobs while I sucked his dick. It was so much bigger than I was used to. A few minutes later Beth started coughing and I quickly moved up next to drew and he covered himself up. Drew told Beth to take a drink and she didn’t answer, she was still asleep. We laid there for a few minutes probably to make sure she was still asleep. After a few minutes drew reached around and started grabbing and rubbing my ass. He stopped and then a minute later he started doing it again. He started to make his way around towards my pussy when she started coughing again. He told her to take a drink and she said no and went back to sleep again. After a minute of me struggling to get to his dick because his back was to me, he reached around and started rubbing my pussy through my leggings. He then reached in my leggings and started rubbing my clit and fingering me. Maybe it was all the alcohol, but it was so amazing. He was so good with his hands. A few minutes and two orgasms later, I went down on him again, probably for about 15 or 20 minutes. He had his hand on the back of my head, pushing his huge dick farther down my throat. I didn’t mind, he was enjoying it. I pulled out for a minute to catch my breath and started giving him a hand job and he came all over his stomach.

Did you have an orgasm? Did your partner(s)? Yes, 2 for me 1 for him

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nope

What were your REASONS for having this hookup? I enjoy feeling wanted

Were alcohol or drugs involved? If so, how much? Yes, I had 4 shots of southern comfort, 3 twisted teas and a mixed drink. Also smoked a lot of pot. He was completely sober.

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? We went to sleep. We barely said anything to each other in the morning. Talk about awkward. I dont think I regret it. I would definitely do it again with him, maybe even more

To whom did you talk about the hookup? How did they react? No one

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? No

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 best was that I love feeling wanted and I could tell he wanted me so bad. I now think sex has nothing to do with love, it is something we are programmed to do and it doesn’t matter for the most part who you do it with.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? A little negative

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