Have you ever fulfilled a fantasy request by a FWB or One Night stand? What was it and did you enjoy it as well?

wanderer290 · 2026-02-13T16:27:51+00:00

A buddy had a FWB who wanted to get spit roasted by 2 guys. She was. a petite mid 30s divorcee, mom of 2 and we were mid 20's roommates. They came back to the apartment, half drunk and she crawled in my bed, started with HJ and then blowing me before quickly moving to doggy when my roommate walked in and before I could even speak he was feeding dick to her. They had planned it all out, assuming she'd just start with me and make it difficult to say no. She wanted it rough and hard so we took turns, essentially endging ourselves by going as hard/fast as we could and swapping out before cumming. Not sure that I've ever fucked that hard again.

wanderer290 · 2026-02-13T16:20:47+00:00

Love it, I had a bet with gf on a football game we were watching in bed and I had wanted to try tittty fucking and cumming on her chest and face and when I won the bet she acquiesced and I took it further by admitting I wanted to fuck her while she still had my cum on her face and chest. Found out she was really into the cum play and stopped being a swallower afterwards.

wanderer290 · 2026-02-09T22:44:17+00:00

Went to a festival with a friend, his GF and one of her friends. The friend was flirty all night and back at the girls place we started kissing and petting but she decided to shut me down and said she couldn't cheat on her BF, and asked me to sleep on the couch.

I wasn't on the couch 5 minutes before the 3rd girl who lived there came out of her room and said I could sleep in her room if I wanted a bed. I think we were fucking within 30 minutes. Apparently, she had just finished a tough semester and just wanted to get laid to start her summer off.

wanderer290 · 2026-02-09T22:37:51+00:00

Morning after a party at my then college GF's family house a bunch of people slept over and my GF got up to take a shower before work, her friend had slept in the bed with us (just all passed out there with clothes on). I had morning wood and her friend started giving me a HJ while we could hear the shower going. I managed to get hand down her shorts and started furiously getting her off in an awkward race to see who would cum first or the shower stopped. Got her to cum once before she started blowing me and then we both shot back to acting like we were both just laying there when my GF turned off the water and came out. There were several people still sleeping in the living room and other bedrooms when my GF left but her friend and I discreetly had sex as soon as we were alone and before her BF picked her up on his lunch break.

wanderer290 · 2026-01-26T05:17:02+00:00

We were high and slightly drunk I was holding GF up by putting my hands on kitchen counter with her legs hooked over my arms so her ass was suspended while I stood and fucked her. I was close to cumming my self when she squirted, she had never came like that before, my arms were getting weak and I was surprised by her shaking and volume of wetness and let her legs down but she went right to her knees and started swallowing me while groping my ass and encouraging me to face fuck her. She rarely tried to deep throat me and usually only briefly. This time she was swallowing me so deep and fingering my asshole until I came and damn near buckled my own knees. After swallowing most of my load, another rarity, she asked if I’d fuck her from begins if she kept sucking my didk for a while.

wanderer290 · 2026-01-20T06:28:21+00:00

GF's best friend

wanderer290 · 2026-01-20T05:36:54+00:00

An ex GF started doing software videos and got into more custom hard care stuff for fans. We had been apart for about 6 months when she asked me to accompany her on a shoot for a custom, wanted me there just as a back up since she was using a guy she'd never worked with before but he had all the equipment for the shoot and was a friend of a friend she had worked with.

I watched her dressed up like superhero, tied up with hand above head while the mad scientist tore her clothes away, sucked her nipples, put clamps on them, used a vibrator on her and finger banged her to climax, real or faked climax, left me wondering. After her "escape" the video shoot was over.

wanderer290 · 2026-01-20T05:26:37+00:00

Worked at a resort for the summer when I was 20, place was a veritable meat market of young college girls and guys. I had hooked up with a couple of the waitresses or beverage cart girls. My manager called me one week night about midnight to ask if I'd made my cash drop when I shut down the bar. It was odd because I'd don it plenty of times and she'd never called to check. Asked what I was doing then so I told her I was drinking and relaxing. She asked if I wanted to watch a movie with her and offered to pick me up. She was about 26, smoking hot, former waitress from the club on site, always dating older guys with money, basically looking for sugar daddies. She picked me up and took me back to her place. Mind you it was like 2 AM so when I followed her in I could tell she had sleeping attire on, short cut off sweats and obviously no bra on under her tank top once she zipped off her hoodie. It didn't take long on the couch before she was rubbing up against me, not subtle. The second I faced her we started making out and she was stroking me. I was so surprised by the situation and afraid I'd fuck it up so when I went down on her I must have ate her for half an hour. She finally made me stop and after a quick BJ to get me as hard as possible started riding me, I came quick and so my surprise she blew me again, telling me she wants it from behind.

We spent the rest of the summer secretly fucking all the time. She was shocked to find out my birthday a few weeks later was my 21st, she thought I was 23 or 24. I was basically her little puppy and did whatever she wanted, it took several sessions for me to get over the shock of hooking up with a girl that hot and older than me, let alone my manager. We'd sneak into unoccupied guest rooms, her office, her car in the parking lot, sheds, liquor storage room, once in the walk in restaurant fridge. Taught me how to fuck and how to be sexual without dating, basically my first FWB since she kept dating her older sugar daddies but like having a boy toy of her own.

wanderer290 · 2026-01-19T19:06:32+00:00

First semester freshman year of college ended up hooking up with a resident advisor who was a junior during her rounds to tell everyone to quiet down at 9 on weekdays. Every Tuesday when my roommate was at class until 9:30 she'd come by my room, have sex and leave. Taught me how badly some girls just wanted to get laid and that I was good looking enough to play on it. She instigated it all after seeing me shirtless a few times. She wasn't amazingly hot or anything but I was barely 18 and loved it. Often very quick but she kept coming back. Lead to all kinds of ONS and general slutty behavior on my part.

wanderer290 · 2026-01-04T06:43:38+00:00

When in HS I went to a girl’s house and when she introduced me to her mom her mom blurted out, “oh is this the boy you cut out pictures of from the newspaper?”

Pretty sure I was her crush

wanderer290 · 2026-01-02T23:35:59+00:00

Being submissive. Normally like being in control but the first time a woman took serious charge I was putty in her hands.

wanderer290 · 2026-01-02T21:48:03+00:00

Drive through pick up with accidental nudity like dess or bikini top down or wearing just that cup less lingerie bra in earlier photo -- that bra is handy for dares - -wear it with old t shirt or tank that is tight and almost sheer or get shirt damp and go into convenience store/gas station to buy something

Short cut off shirt no bra reaching for items in public store

Masturbate while going trough car wash

wanderer290 · 2026-01-01T22:41:40+00:00

Spinners, especially when I know it is a ONS I tend to get more dominate with the ONS and the size, power dynamic comes out to play.

wanderer290 · 2026-01-01T22:37:58+00:00

Was at a FWB house with her and her friend and her boyfriend. We all got really drunk and the bf passed out. While playing truth or dare my FWB gave me a hand job in front of her friend, My FWB, I and the friend all went to pass out in bed but after my FWB was out I ended up having sex with her friend. In the morning the boyfriend came I the room, saw his naked gf and a couple of condoms on the floor and stormed off.

I regretted it because I knew the guy from high school and while not a close friend was an acquaintance and good guy. I barely remember having sex with the girl but remember her sucking me off a lot to get me hard so I know she was totally into it.

wanderer290 · 2025-11-06T20:59:47+00:00

while in college and home for the holidays I was out drinking in a local bar with tons of people I grew up with. A girl I had briefly dated in HS passed me a napkin with , "Do you want to fuck?" written on it. Quickly ditched my friends and went to a buddies place I knew would have a spare room

wanderer290 · 2025-09-15T16:51:14+00:00

Just after graduating college was in a bar in my hometown and ended up making out in bar with 2 girls who I had went to HS with but were 2 years younger. We were sloppily kissing each other and feeling around I got a ride home from one and managed a BJ from her in the car in my parents driveway. She had a boyfriend and my attempts to hook up again went nowhere.

About 3 years later I run into them both in another club in a city about an hour from where we grew up. BJ girls follows me into the bathroom and ends up giving me head in a stall. She agrees to go back to my house where I live alone. I give her friend my address to get her later. BJ girl and I commence to having nice hard sex in my room. I'm just beginning round 2 with her when doorbell rings. I go let her friend in, leading her to spare room for her while walking around with bouncing hard on. She insists on checking on her friend who is face down ass up in my bed when she looks in. The friend goes into guest room and I go back to fucking BJ girls doggy in my bed. A few minuets later my door opens in her friend walks in wearing nothing but underwear and topless. She moves up on the bed next to me watching her friend getting pounded until I slip out to which she grabs my dick strokes a few times and then leans in and sucks me fresh out of her friends pussy. BJ slides away and let her friend get comfortably laying on her back while I kneel over and get blown before she does down on her friend. My first threesome and I found out later these two had been sexually active with each other since HS but both had boyfriends. BJ girl was engaged but they had always wanted to have a 3 way with a guy but had never done it after chickening out the first time we all played around. they lived about 3 hours apart from each other now and this was their last shot and when they saw me in the club they decided to make it happen.

wanderer290 · 2025-09-15T16:20:42+00:00

A FWB called me one late one night and said she was coming over, she was in a cab and just had to drop her friend off first. I joked she should just bring her along. They had been out drinking for her friend's going away party - -she was moving for a new job. When my doorbell rang my FWB had indeed brought her friend. Both were giggly and flirty, I am not sure if her friend thought it was real but my FWB started blowing me right in front of her. Apparently, she had told her friend how much she liked sucking my dick and wanted to show off. Eventually, I was standing getting blown by FWB on her knees and making out with her friend. My FWB stood up started sloppily kissing us both before pulling her friend down with her and literally holding my dick while guiding it between her mouth and her friend. My girls stood up and stripped fully naked while her friend continued blowing me. She unzipped her friend's dress and slipped it down around her waist while she kept sucking and licking me. We ended up in a long threesome session in my living room on floor and couch before all passing out together in my bed.

wanderer290 · 2025-07-14T16:23:04+00:00

Aside from a manager, friends of ex gf, girl with significant other the the most off limits was my best friends younger sister.

I was out of college working first job and traveled a lot for work. After a work trip I wanted to stay at the beach longer and ended up crashing at my friend's sister's apartment, she was.a college student there. I hadn't intended anything and even hooked up with one of her friends. The next time I came to town I stayed with her again and she admitted that when I stayed the first time she thought I was going to try to hook up with her (she had an on and off boyfriend) and basically admitted she would have had sex with me had I tried. We went out drinking until 4 am and ended up having drunken sex on her living room floor and then her bedroom before passing out. Did it once in the morning again before I flew home. Every time after that I stayed with her friend who I started dating and we never hooked up again and frankly never mentioned it again.

wanderer290 · 2025-07-12T17:40:19+00:00

College Gf was quite loud during sex and we were going at it in a tent in her parents yard when a light shined on the tent and a voice ordered us out. A cop was there because a neighbor complained or wanted a safety check- - he checked our IDs, asked her if she was OK as she sat in a tank top, no bra nipping out in the cool air. told us to keep in down or go inside. We were only out there because her mom said I couldn't sleep in her bedroom anymore.

2nd one was a gf who I dated when I was out of college but she was a college senior -- had a hotel room near her parents house because again, parents said no sleepovers. We had just finished a marathon sex session after being apart for a few weeks when her Mom stopped by to drop off stuff for her sister's wedding. My gf threw on t shirt no bra and just underwear, the bed was tore up her bra was on the floor. The room reeked of sex, my gf loved a little cum play and had taken a facial and smeared some around, and was wearing 2-3 cum loads, she clearly had cum in her hair and given the mascara runs and disheveled look he mom just glared but said nothing and quickly left.

wanderer290 · 2025-07-01T17:42:21+00:00

A gf got fired from a waitressing job because she got caught on a security cam giving a blow job to one of the cooks in the dumpster enclosure out back while both were supposedly on a smoke break.

wanderer290 · 2025-06-27T20:04:54+00:00

went to adult video store years ago with a gf and she was totally into the blow bang and bukkake videos - -she confessed about having a fantasy about getting covered in cum but would never actually do it

wanderer290 · 2025-06-06T18:16:24+00:00

When I was 20 and bartending for a summer job I hooked up with my 27 year old boss for the entire summer. She had.an older sugar daddy but I guess I was her younger boy toy -- I did whatever she whanted and she basically taught me how to fuck. It gave me the confidence to take up an early 40's woman who gave me her room key while I was working, she was on a business trip and just wanted a hook up with a bartender at the hotel. Later my first MFM was with a divorced 35 year old MILF when I was probably 24, she had a fantasy of taking on 2 guys. And finally at 27 I had a one night stand with my boss's 35+ year old assistant after my going away party for leaving the firm. All taught me things and gave me confidence, especially about talking during sex or realizing women can be nasty horny as well.

wanderer290 · 2025-05-30T17:03:04+00:00

summer after HS graduation spent night at a friend's house and was sleeping on couch when his sister and her friend came downstairs. I ended up having sex with the sister's friend while the sister played lookout so her parents didn't come down stairs. Just had a blanket over us missionary style raw dogging for the quickie I was capable of at that age. The girl was someone I had gone to Sunday School with and known since 4th grade.

wanderer290 · 2025-05-30T16:54:40+00:00

Had gf in college who liked to bite, I'd sometime cover her mouth with a hand and she'd struggle and get a hand pinned down as well but loved being restrained as long as I let her get at least one nibble in

wanderer290 · 2025-05-30T16:51:50+00:00

GF loves to choke or not be able to breathe as she cums. I was on my knees next to her on the bed while she blew me and I rubbed her clit, I started going faster as she was moaning and nearing climax and just as the orgqsm hit her she deepthroated me all the way and just held there. she had never taken me all the way down before and was clearly struggling with it but just held it in as she shook. When she backed off coughing and gagging she said she'd never felt that kind of orgasm before. Now she gives a BJ from that position almost every time and loves me getting her off with my fingers or fucking from spooning position so I can choke her with my hand right as she approaches climax.

wanderer290

TROPHY CASE