In My Pants

The first time was with my girlfriend in high school, Elaine, who was virginal, shy, timid, and totally ignorant about sex when we started dating. Her father was religious and strict but as we dated several years, Elaines curiosity progressively led her to explore my body more and more. I was stopped any time I tried more than kissing, rubbing her breast through the blouse and bra, touching her butt under the skirt but over her panties, and enjoying her sitting on my clothed lap. She'd gotten more and more bold to where she'd have my pants open and pulled part way down as we made out, fondling me by reaching inside my briefs. I loved it, of course, but craved to touch her back.

After she started feeling me through my briefs, though, she also learned from reading and from asking me that I could ejaculate and that was an orgasm for me. That became her goal but I couldn't tell because she didn't know how to cause it. She always managed to do a lot of light touching that got me to leak precum like a faucet and so she thought I was having an orgasm. Instead I was getting terrible blue balls.

I guess she didn't realize it until our church showed a Focus on the Family video that approved of masturbation. I was beet red sitting there holding her hand, watching that in the Sunday night congregation. Later that week, Elaine and I were on a date and as we were talking she surprised me with her uncharacteristic directness, "Do you do that? You know, like the preacher in the video said?"

I was honest and said yes. Her face turned bright pink. She was quiet for a minute at least." Like when?" I told her when I was home alone. "Do you do it a lot? Like the video talked about some boys need it more than others but you have to be careful not to do it too much." I said I did it enough to help the feelings. Her questions led to her finding out I always did it after a date and she asked why I needed to after she did it for me already. So I had to explain that I'd never ejaculated but loved her touch, reassured her that she was very pleasing, and explain the precum I leaked. I also ended up describing what it was like when I came, how messy, how it shot out. Oddly, we barely made out that night before I took her home. I thought I'd ruined touching me for her by telling her I had never actually had an orgasm with her.

But, the next date she was amorous and driven. She went much more quickly to touching me all over than she had ever done before and was rubbing my penis like crazy through my pants. After she opened and pulled them down a little, she touched the wetness and sniffed it, then smiled at me. As we kissed, she didn't do the light touches but was more aggressively rubbing all over. I got so close! We had to go because we were expected somewhere and I sensed her disappointment. The next date we parked again and it was the same except somehow she had learned about the penis head. With that unskilled but persistent groping, our kissing, and my hand on her butt down the back of her loose jeans, I came hard. She pulled immediately pulled her hand off me with a loud, "Oh my."

I groaned, "Please don't stop." She put her hand back and squeezed, sitting back to stare.

After I was done, she sniffed her hand again, then reached back to my very wet briefs and felt the goo oozing through, feeling my penis head, rubbing the goo around. She told me she was amazed and that it was gross but very warm and sticky, that there was so much more than she thought there would be, but so cool to feel me throb, and asked if I was ok. I sighed, "I'm way better than ok."

"Maybe you better not walk me inside tonight. Dad could see the mess," Elaine suggested.

Another woman who made me cum in my pants was TammieJo. She was a woman who ran hot and cold sexually and liked being a tease. She often work very short skirts with sheer panties or gstrings, liked to have her cleavage show in tight sweaters. Her daughter was staying with her father so TammieJo and I got to go shopping alone for clothes for TammieJo, which was always a lot of fun and sexy, too. She had dressed braless and only sheer to waist pantyhose on the bottom. The whole time, she teased me as she tried on miniskirts, short dresses, and tight tops that let her nipples show. We even went to Victorias Secret and she tried on bras, letting me see, and gstrings. I bought her a number of sexy things and two complete outfits with very short skirts. The whole time I was carrying either a partial or nearly full erection in my tight jeans. If my hooded sweatshirt had not been way too long, I'd have been chased out of the store.

When we got in my car, she put her hand on my thigh. "You liked what you saw. I could tell."

I admitted I did and asked what we should do next. She said a quick dinner because she had play practice at 7 after which she had to pick up her daughter. I complained that I needed her and wished that we could make love. "Is your little dick aching for me?" TammieJo teased. Her hand moved to grip my still swollen penis. I moaned and told her I needed her so much, that she was beautiful and sexy all day. She asked to go to a restaurant across town nearer to her apartment and I began the drive.

Her hand started to work on my penis. She was always very observant when we made love and had learned just the right things to do to me. Soon I had a wet spot the size of a quarter. I said that she was making me ache. So what? was her response. I sounded so pitiful saying that leaving me hanging was mean. She teased back, "Who said I was going to do that?" I said I didn't want to be embarrassed at the restaurant to which she just shushed me. Her fingers and thumb went to work in her expert way and before we got to Maggianos I came in my pants. I managed to keep the car on the road while she made me gasp with pleasure. She laughed at the big wet stain that extended down my inner thigh when I came around to open her car door. I still remember walking funny to try to hide it.

Even more recently, my wife wanted to make me cum in my pants. One night before church she and I were hugging and kissing after dinner was finished. She said she needed a nap or to lay down, she was tired from not sleeping well, and asked me to lay with her. Usually that meant she would snuggle to my side and sleep, I'd wake her on time, that's it. This time started like that until she put her hand on my chest and felt my nipple through my dress shirt. "Mmm. Your nips are always hard," she commented. She played with it a bit. Her hand sat still as she drifted off momentarily.

Then her hand traced down to my groin. She found my penis and began to play lightly through my dress pants until I was rock hard. Neither of us said anything but as she played I reacted with ooh and ahh as she hit the right spots. She kept drifting to snooze then waking to rub, so after an hour I was very on edge. I started rubbing her back to wake her to get ready to leave, told her it was almost time. "Hurry up, I want to make you mess," she said. Because she's never really learned what gets me going the most, I had to start moving my hips like I was trying to fuck her hand or my pants and finally I clenched all my muscles and came.

She got up and stretched. "You better change your pants. I can see the cummy spot. Hurry because I was to stop at Panera for coffee and now you owe me."

Is there a secret thrill in getting a man to squirt in his pants?