When I first started using a flogger on my partner, I accidentally whacked him across the face… Whoops. When we first tried using candle wax, I burned him. He has a little scar on his chest now. I feel so abusive. He laughs every time it’s brought up. Just about every experiment we’ve had together has been hilariously awkward.
I once fell down a hill, all because I was trying to give a blow job. This happened when I was in high school, blow jobs were about as far as I had gotten sexually, and I was REALLY awkward about anything sexual. Also, it was in a time before I had a car or a place of my own, so my boyfriend and I would go to the woods to hang out and fool around. Well, we were standing in the woods at the top of a small hill and I tried to kneel. I stumbled, and started somersaulting backwards down the hill. And he started chasing me with his pants around his ankles. By the time I got to the bottom, I was covered in dirt, twigs, and leaves. This did not help my sexual awkwardness. Not one bit.
So, I’m a guy. A female friend of mine came to visit me in the middle of the night with a girl she had recently met (and for added spice worked at a sex-hotline). They wanted to crash my place for a couple of hours to wait for their ride out of town. They had woken me up so I just sat on my bed chatting with them. My friend came to sit on the bed with me and, before long, there was touching. The other girl was using my computer at the time. Things got pretty heated and after a while the friend saw what was happening and came to join the fun. That’s when it turned bad. The thought that this fantasy of every guy might be coming true hit me like a ton of bricks and … I don’t know. I panicked.
I sat up and said: “I’m making noodles. Who wants noodles?” I jumped off the bed and walked straight to the kitchen, feeling their “What the SHIT!?” looks on my back. Then I just stood in the kitchen looking at nothing and ended up making noodles with added tears. They left soon after.
I still sob a little when I think about this.
I’d just started dating a girl. I’d been drinking and smoking, and I’d popped in a piece of gum so my breath wouldn’t stink when we made out. After some smooching, feeling up, and whatnot, I went down on her. Then we had sex. The next morning, when I was taking a shower, I noticed some white, sticky stuff on my cock. Not cum. It was thicker and tackier. I thought maybe it was some weird discharge from her. I cleaned it off, and then business as usual. After a few months of dating, she confessed to me that the day after our first encounter, she’d found the same thing in her pubic region. It was my gum. Apparently, when I was eating her out, the gum in my mouth got stuck in her pubes.
In college we had a dorm meeting downstairs to introduce some new residents. This girl was a firecracker to say the least and after the meeting I knew she was going to fit in well with our group of friends so I invited her to play cards with a few folks. After a few rounds she suggested changing the game to strip poker, so we headed up to my room, which was the hangout room.
So, two ladies, myself and 3 other men (4 men, 2 ladies) headed up to our room to play strip poker. As soon as we landed on the beds, because there was no where else to sit, the cards were forgotten and a make out/clothes on orgy thing happened.
Imagine, if you will, a man(roommate) kneeling betwixt the legs of new girl eating her out while she was sitting between my legs with her back to me. I was fondling her and playing DJ for mood music. Another guy was sitting to my right and the last lady and and man were doing their thing to his right.
Now it’s important to note that the dude to my right was a HUGE asshole, but he was the first friend my roommate and I made at college so he still hung out with us.
So the asshole was sitting between the couple going at it and the weird 3 some thing going on when, as I would find out later, both the ladies who had a crush on him, simultaneously went to give him a handjob because they felt bad for him not getting any action.
One of the ladies won out and got to do the deed. As the jerk came it kind of quieted the room down as he was the only person to reach a climax. In his ecstasy he slumped to the side and sort of landed on me. It was an awkward position so I put my arm around him. As the room lay in quiet, everyone basking in our mutual afterglow I said in a clear voice, “I bet you never thought a man would be holding you while that happened eh?”
For the rest of my time at college whenever this douche started to get out of line I would just start to tell the story of how he came in my arms and all of a sudden, he wasn’t such a jerk anymore!
My boyfriend and I finally decided to do it after having multiple talks about making sure the first time would be special. Afterward, I mused ‘I can’t believe I’m not a virgin anymore,’ and he freaked out! Turns out, he thought we had been talking about having our first time together. He kept asking ‘Did I hurt you?’ and ‘Are you okay?’ which got to be way too much after a while. He ended up being the emotional one, not me!
I went the movies with my boyfriend at the time. Being the horny couple that we were, we both thought it would be super hot to get it on in the theater! We selected our seats carefully, so we could both have a good view of the film while keeping our eyes on the doors. It was one of the most unforgettably sexy experiences of my life. When it was all over, we sat and watched the rest of the film, but as the credits rolled, I went to gather my coat and scarf and noticed a couple was sitting behind us, a few rows up! They had a perfect view of our antics! Neither of us had seen them come in (like I said, it was pretty hot and heavy), but we were mortified and ran out, laughing hysterically.
My first time was definitely awkward. The guy I was with kept saying stuff like ‘How’s that for you, you dirty girl?’ and ‘Tell me how much you want me.’ He also dragged me into about 30 different positions. I felt like I was doing Pilates! When we were finished, I went to hug him but accidentally swung my hand out too fast and ended up whacking him really hard on the penis. I was embarrassed, and he was in pain. At least I can laugh about it now.
I was staying in a hotel with my girlfriend. The hotel was pretty nice, but the room I got had 2 double beds instead of a queen or king.
So we had just finished going down on each other, had a bunch of sexy foreplay, intense kissing, all that jazz. We are both about to explode from teasing and so I grab her by the hips and pull her into me. This is about to be the hottest sex ever. So I move up so we can start getting down. I put my arm out for balance and forgetting that I’m in a double size bed, my hand completely misses the bed. I go falling off into this chair, and at this point all she can see is my ass up in the air while I try to get up.
She literally laughed for 30 minutes, and we had to postpone sex for a couple hours because we would just start laughing hysterically any time we tried.
As a freshman in college, I decided to nurse the wounds of a bad breakup with a one-night stand. I should have run in the other direction when the guy told me he was working on his “memoirs” (he was 19), but I was pretty desperate. The sex itself was awkward, passionless, and boring, but the real treat came the next day. I arrived back to my dorm room in last night’s clothes, and as I was changing to head to the showers, my roommate noticed something weird on my ass. Turned out the guy had drawn on me while I was asleep…a sailboat, a cat, and a rocketship, all on my butt, all in highlighter.