Female Boy Sex Stories

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Female Boy Sex Stories
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Alexis Jones
Assistant Editor
Alexis Jones is an assistant editor at Women's Health where she writes across several verticals on WomensHealthmag.com , including life, health, sex and love, relationships and fitness, while also contributing to the print magazine.


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The great thing about sex (besides the orgasms , of course) is that if you make a mistake or something awkward happens, you can always laugh about it later.
Have you ever given a blow job in an Uber and lost your nose ring? What about doing it in a J.Crew bathroom while the clothing attendant was right outside? No? Well these real women have—and they're willing to share their funniest stories with you. Trust me, you're in for a laugh.
If you're not either in tears after reading this or ready to risk some jail time during your next sexual encounter, read it again. These 50 women have risked it all for The Big O...you might want to try it sometime.
"We can roll with it, or you can let me borrow your razor."
"I was hooking up with this dude for months, but it wasn't consistent, so when I went over to his place I realized when I got there that I was not, let's just say, 100-percent prepared down there. I explained the situation to the dude and gave him two options. 'We can roll with it, or you can let me borrow your razor, with a totally new razor head' (because duh, bacteria!). He opted for the second choice. And I hopped in the shower, still drunk, and shaved everything. How I didn't slip in the shower or cut myself while drunk is beyond me, but mission accomplished...and the sex after was actually the best ever with that guy, so yeah!" —Heather R., 26
"I was hooking up with a guy and I didn’t eat much that day. When we got in the shower to have sex, I actually started to pass out. The guy had to help me out of the shower, dry me off, and basically became my doctor. I was so embarrassed." —Emily B., 24
"I was hooking up with this guy for about three months, but he would always come to my place since I lived near the town center with all the bars. But one night, I finally went to his house to hookup, and when I went to bathroom to clean up afterward, I noticed a bunch of kids clothes on the floor and a small toothbrush. Turns out, he had an whole child. Three months and I never knew!" — Melanie C., 24
"This man had popped a couple of Tic Tacs while he was down there."
"I was hooking up with this guy who didn't like giving oral. But I pushed him on it, because equality, and he finally agreed to give it a try. As soon as he got started, I remember feeling something weird down there tingling and burning. I soon realized that this man had popped a couple of Tic Tacs in while he was down there without letting me know. WTH, dude?!" — Isabelle M., 26
"Apparently his dick was burning. Sorry to this man."
"I was making this spicy stew recipe online that called for a bunch of habañeros. I washed my hands pretty well, but I guess they still had pepper on them, because later that night when I was giving a guy a hand job, he started making funny noises and started yelling, 'Oww, owww.' Apparently, his dick was burning. Sorry to this man." —Ilena B., 26
"I couldn’t help but try to solve the math problem."
"The first time I had sex with my high school boyfriend, we were at his parents' house alone. We went up to his room, and he laid me down on the bed. But just as he put it in, I looked up at the ceiling and noticed he had derivative math equations taped there. The entire time, I couldn’t help but try to solve the math problem. I told him this wasn't going to work for me and we went out for pizza instead." – Ashley L., 24
"I've never questioned my life choices more."
"It was the night of my boyfriend's fraternity formal. We were having a good time when he asked me if I wanted to sneak away from the dance floor. We ran to the men's bathroom, picked a stall, and started having sex. That was, until three of his brothers came in to use the bathroom. They started chatting it up at the urinals. And we were just in the stall, naked, trying to remain as quiet as possible. That's when I snapped back into reality and realized how disgusting this bathroom was. I've never questioned my life choices more." —Amber G., 24
"That didn’t stop us from catching up in the laundry room."
"One time at a house party, I spotted my crush walking in from across the room. We hadn’t talked in a while, but that didn’t stop us from catching up in the laundry room of our friend's house. We were literally having rough sex in the laundry room while people knocked loudly on the door because they thought it was the bathroom." —Denise B., 25
"He sat me on a random car parked in the alley."
"When I first moved to Brooklyn, I came across a NSFW profile on Tumblr with this guy who was popular for the sloppy head he gives. So I was scrolling through his profile and came across a post that said something like, 'Repost this if you’re based in New York.' So being new and unknown to the city, I said, hey, why the hell not...and messaged him. A day or so later, we ended meeting up at a Mexican-themed bar. After a few margaritas, we went to a restaurant. When we got to the booth, we instantly began making out and um... exploring each other’s bodies. So we slipped out before the waiter came back and went into the alley right next to the bar. He sat me on a random car parked in the alley and showed me exactly how he became so Tumblr famous." —Sharice F., 25
"Who knew Kyle sounds like Carl in German?"
"I was studying abroad in Spain and met a really cute German guy while out one night. We had a great night together, but the next morning, he told me I’d been calling him the wrong name the entire night. Who knew Kyle sounds like Carl in German?" —Elise C., 23
"I asked if he wanted to join and soon I started making out with my coworkers date."
"One Friday afternoon in the office, my coworker was venting about not having been on a date in awhile. I motivated her to try her luck on Tinder. She eventually met a guy she liked, they chatted for a bit, and he asked her out. But he wanted to know if she had a friend for his friend in town. Of course, I agreed to be her wingwoman. We met up at a lounge and laughed the whole night. But my friend wanted to head home because she had work the next morning.
"After they dropped her off, I chose to stay and hang out with the two guys. Initially, I was only dancing with the date I was set up with, but after a few rum punches, we were all taking turns dancing together. We took a break and went outside to cool off. Outside, me and my original date began making out. After we stopped, I noticed his friend was just standing there. I asked if he wanted to join and soon I started making out with my coworkers' date. Shortly after, we all went to a hotel and that’s the story of my first threesome." —Serena B., 25
"It was the perfect one-flight stand."
"I was on a 12-hour flight, and the guy next to me was pretty cute. I swear he was Ryan Gosling's twin, and he was wearing an army uniform (hard to resist, right?). We started talking, and a couple of hours in, I was trying to fall asleep when he said I could rest my head on his lap to be more comfortable. So I did, but a couple minutes in, I could feel he was getting hard. So I started rubbing his dick. He put a blanket over my head so nobody around us could see, but I'm nearly positive the woman on the other side of the aisle could tell what was happening, especially when I pulled down his zipper and started bobbing my head up and down. Luckily, he came pretty quickly. We talked after the flight up until baggage claim and then never saw each other again. It was the perfect one-flight stand." — Amber M., 28
"I lost my nose ring in the Uber, and I kind of want it back."
"I gave a blow job to this guy in an Uber. It was incredibly hot and we’ve ended up hooking up several more times. But I lost my nose ring in the Uber, and I kind of want it back...but I’m too afraid to ask the Uber driver 'cause who knows what he saw back there?" —Rebekah M., 25
"It was super weird looking at the tons of family pictures on the wall."
"It was my first hookup. We were making out on the couch, and after a while, he asked me if I wanted to go into the bedroom. I said yes, but then he lead me into his parents’ bedroom! I remember him saying he’d just always wanted to hook up on his parents’ bed and they were out of town so we wouldn’t get caught. I just went with it, even though it was super weird looking at the tons of family pictures on the wall while we were getting it on. I gave my first blow job and hand job on the bed of some couple who would come back from vacation, fall into bed, and have no idea what happened in it a few days earlier. I really hope he changed the sheets." —Sydney S., 25
"As I was doing it, I noticed I wasn’t really getting any vocal feedback."
"When I was in college, I was hooking up this guy who smoked a lot of weed. I mean, he was pretty much high 24/7. I liked that he was really chill, but turns out, he might’ve been too chill. One night we were having sex, and he just stopped in the middle of it. I asked him what was wrong and he said he was just too high and tired. Being a generous spirit, I offered to give him a blow job instead and he gladly accepted. As I was doing it, I noticed I wasn’t really getting any vocal feedback or anything. I looked up and saw that he’d fallen asleep! We stopped seeing each other after that." —Alice P., 26
"We got naked in the fitting room and got to it."
"When I was dating my first boyfriend, we always talked about unconventional places to have sex. He said he really wanted to have sex in a fitting room, so we decided to make that happen. I was so nervous. I’d never had sex in a public place! We spent some time just walking around a J.Crew at the mall and made up this whole story to the staff about how we were trying to find him an outfit for some special occasion. Eventually, both of us went into the fitting room, making sure it was empty, and the staff didn’t bat an eye. We got naked in the fitting room and got to it, all the while trying to make casual conversation with each other, so it didn’t seem suspicious. I never thought I’d say, 'I think that shirt would look better with those pants,' while someone was literally inside me!" —Olivia M., 26
"My friends and I couldn’t get away fast enough."
"When I was in grad school, my friends and I were out on the town after a really rough week. I just wanted to unwind and see what I could get into that night. Eventually, this really cute guy and his friends came up to us while we were playing pool and the guy started chatting me up. I was interested, but he refused to tell me his name, which was a little suspicious. But I was just looking to have fun, so I didn’t really care. We were making out, and I was ready to go to his place that night to hook up. But for some reason, he started acting really sketchy. That's when he pulled out a bag of what I think was cocaine, told us he was a dealer, and asked if we wanted to do some. My friends and I couldn’t get away fast enough. I seriously dodged a bullet that night." —Trisha D., 27
"I kept my head down, dick still in mouth, until the coast was clear."
"One night, I decided to be adventurous. And while my boyfriend was driving on the highway, I unzipped his pants and started to give him a blow job. All was well and good until he started swerving a bit. I guess he couldn't concentrate. That's when he noticed a cop car trailing behind us. He told me the car was coming next to ours, so I kept my head down, dick still in mouth, until the coast was clear. When I came up for air, we were both cracking up laughing." — Helen H., 25
"Then they told me that I was their top choice to have a threesome with."
"It was the night before my friend's bachelorette party, and I was staying at her and her fiancé's house. There had been plenty of times in the past when she got drunk and started making out with me (or whoever was around), and her hubby-to-be never cared. So we were in their basement/entertainment room, playing games, and she and I were very tipsy. Next thing I know, we were making out, and her fiancé literally started cheering. 'Honey your dreams are coming true,' he said. I stopped because I was entirely confused, and then they told me that I was their top choice to have a threesome with. I was like f*ck it, and we decided to do it." —Reagan T., 26
"A friend of mine told me that a friend of his from Germany would be visiting the U.S. And since he wouldn't be around, he wanted me to give him the grand NYC tour. I actually ended up have a great time with the guy, and one night after a few drinks, he came over and we hooked up. This man was basically a model and looked so pretty sleeping naked that I couldn’t resist taking a photo of him. I never talked to him again, but that photo will one day be framed in black and white on my wall." — Kimberly L., 24
"I’m sure his bedside manner still sucks today."
"I had been hooking up with this guy who was studying to be a doctor. I went over one night while I was kind of sick and had a cough, but I was horny so I didn't care. He was a doctor, anyway, right? I was certain he'd have some cold meds at has place. After we had sex, I was ready to go to sleep and asked if he had some Robitussin or something. This man's medicine cabinet was empty, and I was up all night coughing while he was passed TF out. I’m sure his bedside manner still sucks today." —Deidra N., 25
"My body flew to the back of the seat—hitting my head hard, tits flailing."
"It was our second date, and we went to go see Thor: Ragnarok . As the trailers started rolling, he started making out with me. But I actually wanted to watch this movie, so I told him to chill until after. Movie ends and we head back to his car. He drives to a more secluded area in the parking lot. And obviously things start happening. He fingers me and then I went down on him. We're both about to move on to full-on sex when he screams. I pop my head up to see a creepy man outside our car in a trench coat. While I'm laughing my head off, my date jumped over me to the driver's seat and shifted the engine from park to drive. My body flew to the back of the seat—hitting my head hard, tits flailing. It was not good. Needless to say, we did not finish having sex. He was too scared the bad man in the trench coat would return." — Pamela L., 24
"It was his girlfriend banging on the bedroom door."
"I was 'dating' a football player at the time. He was popular and whatever, but he had a girlfriend. He told me she was awful and treated him badly. I was young, naive, and believed him. So one night, I was at his apartment in bed together and things had just started heating up when we heard a knock on the door. It was his girlfriend banging on the bedroom door. She must have had a key, which made me feel even worse. But I had to keep silent for about 10 minutes while he yelled from behind the door that he was not letting her in. I was mortified." —Kris W., 26
"I got in line and bought one for my walk of shame."
"I had a one-night stand, and I left her place at like 5 a.m. While I was walking home, I realized her place was right next to Dominique Ansel’s bakery, and people were already lining up for cronuts. So I got in line and bought one for my walk of shame." —Martha K., 25
"He noticed a few white stains on my boyfriend's pants."
"It was prom night, and my boyfriend and I were heading back to my house so he could drop me off. We hooked up in the car in front of an abandoned house in my neighborhood and put our fancy clothes back on. When we walked in the door, my dad was sitting on the couch waiting for us to come home. After recapping the night, he noticed a few white stains on my boyfriend's pants. He asked what it was, and I quickly said ice cream. I was sweating through my dress as my dad stared my date down before finally saying, 'Well, must have been good.' Whew!" — Alexandra P., 26
"He started saying stuff about how he wanted to marry me and bring me back to Texas."
"I met this guy at a bar who was in the Army and briefly stationed at a base near my school. We went back to my place to hook up, but as soon as we started getting into it, he WOULD NOT stop talking. He started saying stuff about how he wanted to marry me and bring me back to Texas, where he was from, and kept calling me his African queen. It was weird and annoying. I immediately stopped and told him this wasn’t working for me." —Patty M., 25
"It all started when a certain TV celebrity sent me a DM. 'Hey <3,' he wrote. We began talking, and it turned out he was in my area. He asked me to kick it later and get tacos. I wasn’t sure if he was for real, so I asked if he was serious and told him I was free at 7. We met up and got tacos, but then he started drinking and became visibly drunk. He asked me if I wanted to have sex with him and be his baby mama. When I said no, he said his cum was gold. I've never laughed harder in my life. I left the restaurant after that and he blocked me on IG." — Carrie S., 28
"I saw my bus driver’s face looking through the rearview mirror."
"My high school boyfriend and I were super into sexual acts on the bus. They kind of became our thing. We decided to kick things up a notch one day with a blow job. We knew this would be harder and less easy to achieve, but we managed. Until I lifted my head up from below and the first thing I saw was my bus driver’s face looking through the rearview mirror. I knew that she knew what we’d done. The walk from the back of that bus never felt so long." — Kelly G., 23
"He shrugged and proceeded to take a pee on the side of the garage while we perched, naked, above him."
"Back in college, when I lived in the dorms and my boyfriend lived in a house with several roommates, we struggled to find a place to have sex...alone. Naturally, that led to us laying out a bunch of blankets on the roof of his garage and having sex up there under the stars. It was the middle of the night and we figured no one would be walking by in our small town, so it weirdly satisfied our public-sex kink while also being more private than our bedrooms.
"But of course, one of his roommates stumbled home very intoxicated while we were up there, startling us as he walked by the garage. We froze, and he looked around, clearly having heard something, but confused as to where it was coming from. He shrugged and proceeded to take a pee on the side of the garage while we
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