by Winston Wolf
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? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? CPA
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 0
Legitimate Best Friend Hook-Up
How long ago did this hookup happen? 7 years ago
What was your relationship status at the time? Dating casually
How would you best classify this hookup? Friends-with-benefits
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? My partner is “beautiful,” which is basically a universal truth. She really is my best friend. She was a national level athlete in college, so she’s a little taller and muscular. However, she’s feminine in every sense of the word; definitely has enough fat on her (not too much) for appealing legs, ass, and breasts. She’s always had a fear of emasculating males due to her build. I was also a national level athlete in college so I always had the build to match her.
I met her when we started working for the same employer right after college graduation. I could see guys chasing her around from the minute I met her; I realized none of those guys would get her and she was playing some game you couldn’t win. Despite being beautiful, she wasn’t a brunette, which I typically gravitate towards, so I didn’t think of her in a sexual/romantic aspect again.
About three years into our employment, we started working together a lot and struck up a good rapport. I then moved into her town and we frequented the bars a lot but on a platonic basis. She valued the fact I never pried about her personal life, and I valued the fact she didn’t criticize me for not being more active. Some mutual friends from work who both respected our need for privacy pointed out I shouldn’t be a “social ret-rd” and ignore advances she might be making. I assured them it was merely platonic.
We were about 26 then, and I did value her a lot as a person, but never “connected” with somebody in that way. I knew she hooked up and kept her business to herself. My criticism of other partners I had before that time was that they were hung up on “rules” (i.e. sex on date #x). She knew of my complaints and wouldn’t judge me, but I didn’t have the perspective I needed to act on her then.
After six months of being close friends, I happened to get into nearly a two-year relationship. My girlfriend was gorgeous, love (lust) at first sight on both sides. She was practically a virgin in her late 20s, which I didn’t know at the time, or until after we had sex. While I said I was fine with more experienced partners, so long as they didn’t criticize me (my performance wasn’t questioned), I realized I needed somebody who needed somebody as understanding as me, plus who I did not have a fear of being critical of my slower advances.
After six years of employment, my BFF decided to quit and travel, that’s when my relationship ended. I shared with her the details about my ex-GF because I felt she needed to know to really grasp what I was going through. She knows me better than anybody. I trusted her with very intimate things, made it clear it wasn’t trying to impress her, nor did I expect any information from her in return. She had become friends with my ex-GF during this time and it was a relatively small social circle.
In my BFF’s travels, she met a man who swept her off her feet, but he lived a considerable distance away domestically. She was so happy when she had a brief stop home and was glowing when she told me about him over dinner. I was genuinely happy for her and expressed such sentiments. When her traveling ended, she rejoined my company, and I moved out of my one BR apartment and rented a house close by her with two other co-workers. We were now in our late-20s.
I was having large house parties every month with my new roommates. We’d get about 50% attendance and it was not a big deal if a friend did not attend. My BFF did not attend the first party and apologized, then for the first time, confided in me about her personal life. She said things weren’t as good as she depicted with her boyfriend, he was not willing to be as flexible to travel to see her. She felt embarrassed because she had told our coworkers about him. Obviously, she had my trust and knew I wouldn’t be judgmental, we had a good talk. That’s the only time we ever broached her personal life.
Within a few months of this living arrangement, I realized I had maximized my potential at this job and started interviewing in other cities, which my BFF knew about. That’s when she started acting aggressively towards me.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months later, at my birthday party, I had a pre-arranged hook-up. Being on the rebound from a long relationship, I was more willing to expand the pool of women I interacted with. This clearly made my BFF jealous. We were separated by my kitchen counter/bar, and when she put her elbows down, her top two buttons were undone. Her breasts were front and center – she hid them well. After a few drinks and knowing her personality, that was a clear invitation to look. I kept talking to her but stared at her breasts the whole time. Later on, we shared another moment where I was able to bluntly stare at her breasts. There was no chance I could hook-up with her that night due to her private nature, I ended up sleeping with the female I was supposed to. However, that did not deter her, but perhaps showed her I wasn’t as “fragile” with being so selective over my partners now.
Once I received my job offer in a new city, I started hooking-up with somebody local just for the sake of it. I was at a bar very close to my house with my hook-up (across the bar) and my BFF (next to me). My BFF told me she was going to get flirty to make my hook-up jealous and to play along. We were next to each other, but formed a small triangle with the bar,
We were both very animated with our hands. I put my arm around her far shoulder in a hug like gesture, then rested my loosely closed fist on her far hip (below the bar). I slowly opened it so my hand was on her hip. She managed to reposition herself, so my hand was on her ass. As she left, she leaned in and I thought she was going to legitimately kiss me but gave me a peck on the cheek.
She whispered into my ear, “She’s going to fuck you tonight.” She gave me a look like she had me but didn’t expect me to act aggressively back. I gave her a look (many women have said my eyes can be piercing), then said, “That’s not even fair,” inferring I wanted to be with her as I assertively grabbed her ass. She wasn’t expecting it but managed to smile as she left. My BFF was right, I did have sex with my hook-up for the first time that night, and the hook-up surely noticed my BFF. This was a week before my farewell happy hour.
My happy hour was a combined effort with another friend leaving the company, so there were about ~70 people in total. I had worked closely with a younger female in the company for the two months leading up to my departure, and it was clear to everybody I was trying to hook-up with her. We were the last two to leave the bar, it was only about midnight, and we made out. She had a new boyfriend, though, and said she couldn’t bring me back to her apartment.
I missed the last opportunity for public transit back home, so I took a $75 cab ride. About 1/3 of the way back, I got a text from my BFF, “If you don’t hook up with [younger female], friends with benefits?” I murmured to myself, “She feels the same way about me, as I do about her.” Granted, we both found each other very attractive, but we saw so much value in each other that we couldn’t help but act on it.
For her to be vulnerable to me took a lot for her, and likewise, she respected the fact that I was discerning in my personal life. I texted her something explicit back to indicated I was very willing, she followed up with a text to come over.
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 walked in her front door, she was standing by the stairs in boy shorts and a wife beater. Even though I was drunk, I made sure I savored those steps towards her, very few people get such an opportunity. She was so coy, very different from her outward persona. I lifted her chin with my finger, brushed her hair back, and made eye contact with her as I went to kiss her. To this day it’s still the best kiss I’ve had. I said something to the effect of, “It’s powerful knowing we’re both here because of the value we see in each other, and we’ll be able to look each other in the eye tomorrow no matter what happens.”
We got up to her room and were aggressive and clothing came off quickly. We did train together at the gym, so she had a very good idea of how I was built, but I was comfortable around her in such a manner – I wasn’t trying to impress her. However, we both had the philosophy of not flaunting our bodies, but it didn’t resonate how she made herself appear more modest until I saw her naked. I said something so primal, I sounded like a teenager, making an exclamatory statement about how great she looked naked. To this day, her ass is still the most physically attractive thing I’ve seen. She can’t hide it completely, but believe me, she does not flaunt it in public.
Not that I’m a huge stickler on traditional sex roles, nor am I somebody who enjoys degrading women, but it was clear I was the assertive one the whole night. She knew I had a photographic memory and I kept changing positions. She also knew from what I had told her about my ex-GF, I wasn’t big into doggy style, but with her ass, I had to go there.
Before I knew it, I was fucking her harder than I had ever fucked another woman. Part of it was knowing her, part of my allure was I wouldn’t be emasculated by her (we are roughly same height, I outweighed her by ~60 pounds; I was never more muscular than I was at that time.). Her head was buried in her mattress and she would let out moans and grunts periodically. I then put her on her stomach, my favorite position, and managed to even be more aggressive with her. Subsequently, I figured out that if I can be totally uninhibited with a woman, I can objectify her – it sounds like a paradox. However, if something wasn’t okay with her, she definitely would’ve let me know without judgment.
I put my arms under hers, then secured her legs with mine. What I said to her was a mix of vulgarities and passionate messages. I was kissing her passionately most of this time, and I could tell she never felt “secured” like that by a man. She relaxed knowing it was clear I found her very feminine, respected her, and had no chance of “escape.” Being face-to-face with her to see her express herself is something I’ll never forget.
For the second round, I said I wanted to fuck her on her couch; her roommate wasn’t home. We went back downstairs, and I fucked her even harder doggystyle due to my increased leverage. Her knees were near the end of the cushion, her hands grasping the top of the couch for dear life, as her face was inches away from the wall. She enjoyed it as the session lasted 15-20 minutes with periodic moaning, guttural noises, expletives, etc. as I fucked her.
How sexually satisfying was this hookup? Very
Did you have an orgasm? No, but I was close
Did your partner have an orgasm? I don’t know
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? At the break of dawn, she woke me up as I had to leave before her roommate got home. Later that day I texted her, acknowledging I was totally fine if that was a one-time happening, but wanted to know I thought the world of her – and had for such a long time. I indicated the timing wasn’t great, but if she, “wanted to see if we could make this work, I was all for it.” She replied that she very much appreciated knowing that, she was humbled and flattered, but she would “get attached quickly” if we continued. I conceded the same sentiment and noted I wouldn’t jeopardize our friendship unless we both were all-in (I was only driving distance away, her “boyfriend” required a plane ride – wasn’t sure of his status at that time, nor did I care).
I didn’t stress over the “missed opportunity” since we had both grown and changed in those four years since we initially became friends. When we hooked up, making me realize she was exactly what I wanted in a woman, I did not worry about her past. Even if she would have made such an advance years before, I would’ve eventually gotten hung up on the number of partners she had – that wouldn’t have worked for her. It took me a while to realize what I learned – unconditional love means you respect everything that makes your partner who they are. Despite knowing she presumably had vastly more partners than me, and me assuming that as well, we were complete equals when we were intimate.
Ironically, we ended up working together years later after she was married. We maintained a healthy level of flirting that she usually initiated with “soft ball” questions to me. I made her smile ear-to-ear with some of the compliments I gave her. We will always be good friends and acknowledged there can be moral victories within the realm of people you have unconditional feelings towards.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication
How intoxicated were you? Completely wasted
What substances did you consume? Alcohol
How intoxicated was your partner? Completely wasted
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? A few close friends (i.e. roommates) who had to help me get my car the next day. They were surprised I didn’t end up with the “younger female,” but not surprised I hooked up with my BFF.
How would you best summarize people’s reactions about this hookup? Relatively positive
Did you get emotionally hurt as a result of this hookup? A little bit
Did your partner get emotionally hurt as a result of this hookup? A little bit
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It had nothing to do with physical appearance, but I was never so physically attracted to a woman once we started being intimate. We legitimately wanted to sleep with each other out of respect.
What was the WORST thing about this hookup? We were both drunk – but that’s the circumstances we were dealt.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes – it was the most important experience I’ve had and made me change my perspective.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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 would like to see women be able to act confidently and enjoy sex without society shaming them. My BFF was very comfortable in her sexuality and it was enlightening.
What do you think about the Casual Sex Project? Great to share perspectives and enlighten others.
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