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.
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.
I was “manually prepping” him and thought it was weird that there was so much precum. Eventually, I flicked on the light to grab a condom and he said “Oh my god, you’re bleeding!” I started freaking out. How could this be?! I just got off my period. My hands, stomach and thighs were COVERED in blood…but my nether region was clear. Then, I look over and I see blood literally GUSHING out of the head of his dick. I was so freaked out I just yelled “YOUR DICK IS BLEEDING” and ran out of the room….
He was more mortified than I was…if possible. He told me about a month ago, he was really wasted and zipped the head of his penis in his pants. Being super drunk, he couldn’t dislodge it, so forced the zipper down/yanked his dick out. He then passed out to later find himself on a blood soaked mattress. The doctor told him he needed stitched to close it back up, but didn’t do it…leaving both his penis and me scarred for life.
I had finally agreed to a threesome with the man I had been involved in a Dominant/submissive friends-with-benefits situation for the last four months. Since this was largely my fantasy that he had wanted to fulfill, it was going to be a male-male-female threesome. I was nervous, to say the least. He had agreed to write up an ad for Craigslist, let me review it before posting, and screen all the responses…We finally settled on one-not my first choice, or even my second, but he actually followed through.
….I knew that if I could see what was going on, I wouldn’t go through with it, so we agreed that I would be blindfolded and he would take care of me, gauging the situation and making sure the Guest didn’t overstep my limits.
I was kneeling, blindfolded, in the middle of the living room, when the doorbell rang… It didn’t take long before Guest was naked and in my mouth. Nor did it take long after we rolled around a little bit and had changed positions that I started feeling little “feather brushes” against my arms. For the life of me, I could not figure out what the feeling was-they were without pattern but distinct and localized sensations against my skin. It wasn’t until I started feeling them on my face as I was essentially tea-bagging him that I realized that HE WAS SWEATING ON ME. The Guest, this man I had just “met” in the loosest of terms, wasn’t simply sweaty, he was sweating large, gross, hairy man sweat droplets all over my face and torso.
That should have been my clue to stop, but I’m a trooper and a bit loathe to cause a scene. Besides, my Man was there, I knew I was safe, and he and I were having fun.
Fast forward to the end of the afternoon. I’m on the floor on my back after my Man and I finished fucking, kind of spent from all the activities, but still blindfolded. I can feel the Guest’s hands on me, and he asks if he can get me off again. Not one to say no to an orgasm, he starts attending to me digitally. But then the sensation changes-it feels as if he’s trying to fist me, but with his palm or something. The feeling is off…and then it hits me: The Guest is an amputee and is TRYING TO FIST ME WITH HIS STUMP! I don’t go for fisting to begin with, but trying to fit his stump in my vagina was just never going to happen, so I stop the scene, he leaves, and I go to the bathroom to clean up.
When I come out, I turn to my Man and ask, “What he missing a hand?”
“Yes he was. I didn’t think it would be polite to turn him away just because of it though.”
“That’s true, but Stumpy tried to fist me with his stump! Without asking! Had he tried to fist me, that would have been bad enough, but stumping without permission is just poor form.”