by

What’s your gender? Woman
How old are you? 26
What’s your race/ethnicity? My dad is white/caucasian & my mom is French Mediterranean
What continent do you live on? North America
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Personal Trainer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? One.

Enjoying A FWB While Engaged To Be Married.

How long ago did this hookup happen? 3 months ago

What was your relationship status at the time? Same as current status

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? I tried to keep this story as brief as possible but I needed to include a little background about myself to help with clarity of my situation. This experience was totally out of character for me but since this is an anonymous board, I decided to include as much detail as possible to help explain my thoughts. I hope by sharing this experience it will help someone in the same situation feel comfort because they are not alone.

I was raised in a strict Christian conservative home and at the start of my freshman year in high school my parents found out had snuck out and had sex with a guy. They got mad, I was grounded for the rest of my freshman year, then enrolled in a private Christian school the next year. After my first week at the new school, I decided to become reconnected with my Christian religion and took a vow to abstain from sex till marriage.

My fiancé has known his best friend for 20 years. They grew up on the same street. I’ve known the guy for 10 years because we went to the same high school. After high school, he joined the Marines then went to college on the GI bill. He currently works for a security company teaching combat training on Krav Maga, & Jutsu. He’s 6’ 8”, clean cut, muscular, blonde hair, piercing blue eyes and looks a lot like the Swedish MMA fighter Alexander Gustafsson (HOT!). He’s a ‘player’ and is very confident in himself. I can see why women are swayed by his charm. Each time I see him, he has a different girl. When my fiancé is not around, he’s very flirty with me. I’ll admit I LOVE the compliments. I work hard to stay in shape and it’s nice to have a guy pass on compliments of my hard work. So, I make a point to wear my tight active wear he is around. He also has the ability to make me blush very easily with comments like, “If you weren’t dating my best friend, I know we would be having sex.”

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months ago he moved into the same apartment complex as mine. We run into each other often and when we do he’s very flirty. Since my fiancé is gone on most weekends, he will come to the pool when I finish swimming laps and talk. I have an open invitation to “card night” at his place. A few of his Marine friends (all of them are HOT) come over for cards, beer and ‘guy talk’ (LOL) a couple of times a month.

I had the day off from work one Saturday and my fiancé was two hours away at a gaming tournament. After my morning yoga and 10 mile run, I was left with no plans. My fiancé doesn’t like for me to wear bikinis in public because it shows my midriff. I thought, “he’s out of town” so I put on my tiny red bikini he doesn’t know I own and went to the apartment pool to work on my tan. BTW: He doesn’t like me showing off my midriff because I had my belly button pierced in college. When I was on the track team, all us girls got belly rings that matched. I refuse to remove it because my normal work attire at the gym is a sports bra & shorts. I asked my employer, he thought it looked good and insisted I leave it alone.

I was enjoying the heat of the sun when my fiancé’s best friend came down to talk. He was sweaty from lifting weights and was wearing a skin tight shirt and gym shorts. His ‘date’ was called into work at the last minute and he had no plans for the day. The conversation started out as normal harmless flirting but on this day, I’ll admit I was being extra flirty back. He was wearing sunglasses but I know he was staring at my bikini bridge. He asked “now that you two are finally engaged, have you guys had sex yet?” Without hesitation and a sound of frustration and disappointment I quickly replied, “no.”

He said, “REALLY? I know he wants to wait till marriage, but you have your own place and you guys ARE engaged.” I said, “EXACTLY!” Then his charm kicked in, he said, “You have one of the sexiest bodies I’ve ever seen. If you were my fiancé, we would be taking care of business VERY often.” I blushed because I loved it when he complimented me.

The conversation got hotter when he asked if we had done anything sexual. I told him the night we became engaged, I was so excited and feeling naughty, I had him come to my place for a surprise. While he was busy texting his friends, I changed into a white see through lingerie outfit I bought the mall for this occasion. I was so horny and felt so sexy wearing it, I walked into the living room and while his face was stuck to his phone, I got on my knees, unzipped his shorts and began massaging his soft penis with my hands. He asked me to stop because he was busy working on his fantasy board. That killed the mood. I changed into something comfortable and after he finished texting his friends, he left, then I was left home alone.

He said, “I wish you would have walked down to my place. If I had seen you walk in the room wearing lingerie, I know my eyes wouldn’t be looking at a phone.” He kept hinting we should go to his place and have sex. I blushed, winked, smiled and showed him my engagement ring. I thought that would be the end of our casual flirting until he became serious and took things to the next level.

He asked me when was the last time I had sex. I said, “It’s been too long. Probably 10 years ago?” I told him I’ve had sex one time in my life and it was my freshman year in high school. He replied, “Ten years is long dry spell. Your body is begging to be f&*ked. We need to be friends-with-benefits.” I knew what that was. He added, “It sounds like you have needs and I’m willing to satisfy with ‘no strings attached.’ I’m not asking you on a date or to call off your engagement. Just pure sex.” His charm was working as he added, “Where’s your fiancé right now? He’s out with friends pleasuring himself in a gaming tournament. You are in the prime years so let loose and live life.” Then he read my mind. “I bet you’re thinking what it would be like to be on top of me grinding right now. Think about it. We can we be friends AND have amazing sex. I promise, he will never know.”

He had a great point with the video game pleasure comment. I’ll admit I could feel my bikini bottoms becoming moist because I was aroused. My mind was made up but I was nervous. It was because I knew he was experienced while I was not. My fear was ‘what if the thinks I’m not good in bed?’ No girl wants that reputation (I work at a gym and hear guys make comments). By nature, I’m very aggressive and competitive so I decided if I was going to go through with this, I wanted this to be the best experience he’d ever had. Then, he looked at me with those beautiful blue eyes and said, “Let’s go F&*k. No strings attached.” With that comment I grabbed his hand and left for his place.

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 got inside and he sat on the edge of his bed. I pulled off his shorts and got my first look at his penis. I know he could tell by my expression but WOW! He was already hard and HUGE! I don’t want to dwell but compared to my fiancé, he’s HUGE! My hands are small so I wrapped both around his warm penis (BTW: I was still wearing my engagement ring which made this more exciting). I put him in my mouth while making eye contact. Just as I got the tip in my mouth and began working my tongue in a circular motion, I felt the tip swell and I heard him grunt. Then he exploded. We were not prepared for the mess so he took off his shirt and I got a wet towel and began cleaning him off. (He’s aware I’m a neat freak LOL). It was also a chance for me to rub his muscular chest. He stood up, gave my bikini strings a tug and both pieces hit the floor. This is the first time he’s seen me naked and he gave me a sexy look up and down.

He gave my butt a firm pop and I asked if he had any protection. He showed me a condom in a gold package. He suggested we start with me on top to control the pace. I rolled the condom down his penis then straddled him. His closet doors were mirrors so I had a great view. I also noticed small I was compared to him. I positioned his penis to my entrance and began to lower myself. I was able to get the entire tip inside but there was a pause as if he couldn’t go in much further. It felt like some kind of obstruction was keeping him from going all the way in. I paused for a second, took a deep breath, then he went all the way inside me easily. The feeling of a warm & hard penis stretching my vagina walls to the max gave me a strong rush of pleasure! It was the best sensation I’ve ever felt in my life! I gushed all over him. I felt bad because it was a lot and it also got on his bed. He was cool about it then smacked me on the butt and we continued. I was having so much fun and he was amazing! We did different positions and he knew every pleasure point on my body. He gave me my first orgasm EVER! I ended up having two. My first orgasm came as a surprise. The second was longer and more intense.

We were doing it doggystyle and with an amazing rhythm. He had hold of my hips while making deep thrusts. He would often give my butt a light smack which I found to be very sexy. The wet slapping ‘skin to skin’ sound was echoing in the room. I know he could tell I was close to climaxing because I began to gush each time he went in deep. He slowed his rhythm down so each thrust would push his penis to the deepest part of me. He was in total control and each time he bottomed out, by body would release a large gush. I was on the verge and he knew it. My body began to shiver as he kept the consistent pace. It built up slowly but quickly became an intense sensation. I could tell he got off at the same time I was did. When it happened, he pulled himself all the way inside me and held it tight. I could feel the head of his swollen penis inside my body filling the condom. I’ve never experienced anything like that in my life! When he finished, he pulled out and the condom was full. I remember thinking, “What a waste. I wish he wasn’t wearing a condom.” I had gushed so much, his bed looked like it had been sprayed with a water hose. I was so embarrassed.

I felt bad about the mess I made so I offered to change the sheets and do some laundry. (He’s known me for years and is aware I have to stay busy.) He reluctantly agreed but grabbed my bikini and in a jokingly tone he said, “If you do any cleaning at my place, you can’t wear clothes.” I played along. It felt sexy running around in his apartment naked. I enjoyed his eyes looking at me too.

It was around 4pm and about to leave when I heard my phone ding. It was my fiancé telling me he didn’t advance in the tournament and was driving back. He asked if he could come by my place around 7pm for a dinner. I replied sure. I know this was naughty but in the heat of the moment and for some reason I replied, “You should invite your friend over. I saw him earlier and his date got canceled. I haven’t noticed him with another girl yet LOL. I’ll cook dinner for both of you.” He replied, “Good idea, I’ll ask him.” His phone dinged instantly with the invite. He accepted.

My new FWB said, “Well I guess I will see you around 7pm?” Still naked, I got on my knees and grabbed his penis. I noticed he was semi aroused so I gave him oral. Within seconds he was hard. I looked at him and said, “It’s just 4 o’clock. If you’re up to it, we’ve got time to do it again.” He smacked me on the butt and we went at it like wild animals.

I left his place with time to shower, freshen up and cook. I was impressed at how well dinner went. My fiancé talked about his experience at the tournament and had no clue I had spent the day having sex with his friend. My new FWB was very cool and acted like nothing happened either. Considering my conservative raising, I was amazed at how well I conducted myself. At first, I thought ‘maybe I should felt bad, dirty or ashamed’ but I never did. Actually, my thoughts and emotions could best be described as excited and satisfied.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I currently find myself hooking-up with my FWB around 3-4 times a week and the wedding is just 3 months away. I’m glad our friendship has remained the same while our FWB relationship has been everything we agreed to, just sex.

Since we began ‘hooking up’ on a regular basis, my FWB has taught me to explore beyond normal ‘vanilla’ sex. I have perfected my orals skills while being open to receiving oral. We start out often with the 69 position. (BTW: He’s tongue skill are amazing!) He suggested we take advantage of my flexibility from yoga and try different positions. Here’s a few position we do often: Cowgirl, Reverse cowgirl, standing up and he supports me, doggystyle, & numerous more but I don’t know the name of them.

The wedding is in three months and I haven’t discussed with my FWB on whether we should continue after I get married. I have a feeling he would be willing. If it does happen, I guess I’ll post another story about my first affair. LOL

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? 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 my college roommate because she’s open minded and was very promiscuous in college and we would still remain friends. She’s the type of person that would never judge me as a bad person for having a FWB.

When I told her the story, she was excited for me and wanted to hear all the details. BTW: She doesn’t care for my fiancé. She’s wished for years I would dump him. She’s a great friend that has always encouraged me to experience different guys before I settle down. In her mind, I’m ‘just settling’ with my fiancé and she insists I deserve better.

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

Did you get emotionally hurt as a result of this hookup? Not at all

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? Having amazing sex with an experienced friend.

What was the WORST thing about this hookup? The only regret I have is not having sex while I was in college. My fiancé’s best friend has been trying to get me to have sex with him for years. I wish I had acted earlier.

Embarrassing moment:
The most embarrassing moment was when I had gushed on his bed so much that I had to do laundry.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was raised to be monogamous and to wait for marriage before sex. Now, I have an idea of why people may become unfaithful in a relationship. In the future, I will never be judgmental when I hear cases of infidelity because there is no clear cut ‘right or wrong’. Each situation is different and there will always two sides in every story.

I don’t feel bad for ‘hooking-up’ while currently engaged. I can’t explain why but I don’t.

I was raised to believe that having sexual relations prior to marriage is considered wrong and people judge that person accordingly

I believe no one on this earth is perfect and we are ALL human and we ALL desire pleasures of the flesh.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? It was easy to post this experience on this anonymous board. I only told my college roommate and if anyone else found out, it would be a disaster for me.

Anyone that knows me would be in shock. I would be the talk of the town. People would judge me and I would be labeled as a whore. If people found out, I’m sure I would have to resign from positions at church. It’s sad that people that call themselves loving and caring would be so mean to fellow friends.

My future mother-in-law would upset with me because I’m like a daughter to her and my FWB is like a son to her family. My mother-in-law and I do lots of things together. I’ve helped her with diet and exercise and she’s lost 40 pounds. I’m being brutally truthfully, if this got out, I worry about loosing her friendship more than my fiancé finding out. Sad but true.

My BFF encourages me to continue having sex with my FWB, which is great advice. She’s also shared a few ideas for me to try with my FWB and he loved them. Having casual sex with a friend is great!

I know I would have different feelings about myself if I had a one-night-stand with a random guy.

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? As a society we have changed how our mind becomes aroused and the body fulfills pleasure. Would the same ‘unfaithful’ judgment apply when a person in a committed relationship, would prefer to spend time with a friend and enjoy the pleasures of a video game?

My FWB hasn’t changed his womanizing ways and I am glad. I would feel bad if he did. I would never want to change him because he’s an amazing person.

My FWB made a comment one time that makes sense, “No one buys a car without a test drive.” What if sex after marriage is not satisfying? Would continuing the FWB ‘no strings attached’ sexual relationship be wrong?

What do you think about the Casual Sex Project? I believe more people are having secret ‘casual sex’ but are reluctant to share for fear of society finding out. This is board is a great place for normal people to share their experiences without fear of judgment.

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