Jason stood only a few feet away from me in my room. Jason was my Mom's boyfriend. Mom was busy making dinner and I had been avoiding him, hiding out in my room ever since he had accidentally walked in on me a week ago. He had gotten the full view of me in my Mom's lingerie, a nice black satin panty and cami set. I was so embarrassed. He had quickly shut the door and hadn't said anything to my Mom as far as I could tell but I had been walking on eggshells ever since. Now here he was in my room.
He stepped close to me. I could smell his cologne.
I've been thinking about you all week, he said. You in that little black outfit.
I could feel my heart beating fast. I didn't know what to do. My legs felt like they were glued to the floor.
He leaned in close to my ear. You looked very sexy in it, he whispered. I was wondering what you had on tonight, he said.
With that I felt his fingers touch my stomach at the waste of my jeans. He began to slide them back and forth just inside of my pants.
I'll bet it's something sexy, he said.
Unfortunately I was. I was wearing a blue lace tanga panty.
His fingers reached further into my pants and I felt him touch the top lace of my panties.
Mmmmm, feels nice, he said.
Oh my God, what had I done. I hadn't said anything since Jason came in and I think he could sense I was frightened.
It's OK, he said. None of this has to get out. I'm sure can keep it in the family, he said. You wouldn't want your Mom to find out, he said.
No, I said in almost a whimper. By now his whole hand was in my pants getting a nice feel.
That's a good boy, he said. Good boy. Although I bet you'd like to be a bad little boy, he said. I felt his other hand move to my bottom. Yeah, definitely a bad little boy, he said again.
He began to kiss my neck and I could feel myself getting hard. He reached up my shirt and pinched my nipple. Man you feel good, he said. I want to kiss those soft little lips, he said. And he did. The next thing I knew it his lips were pressed to mine. What was happening. I felt his tongue slip into my mouth and then we were French kissing. I breathed in his cologne. It felt intoxicating.
And then we were pulled sharply back to reality. I heard my Mother call for us to wash up for dinner. Jason pulled his head back from me and smiled at me. And not a bad little kisser too. He gave my bottom another little squeeze and then walked over to my desk and started scribbling something. He gave me his mobile number and email address and then told me to give him the same. I obeyed and wrote it on a scrap piece of paper. Two minutes later we sat down to dinner with my Mom like nothing ever happened.
That was the start of my relationship with my Mom's boyfriend Jason. It was the summer of eighth grade, right before I went to High School and would become one of the most influential times of my life. I had started dressing up in my Mom's clothes the year before. It started out mainly because I was bored one day. Mom was a nurse and worked quite a bit leaving me home alone quite a bit. Mom was working that day and I was stuck doing laundry. My Mom tended to wear very sexy underwear. Lots of satin and lace. I liked the way they felt in my fingers as I folded them. And so I thought what the hell. That day I paraded around in my Mom's lingerie trying on quite a few different outfits. It was fun and I thought well that's that. After that though my curiosity didn't stop though and I found myself frequently in her lingerie drawer. From there I found myself wearing her under things more and more. At first it was just when she was out but after time I found myself wearing them more and more even out. I did most of the laundry so it was easy for me. The only trick became the bra straps when I would go out. Sometimes I would wear two shirts to hide them or I would wear a camisole top which wasn't as obvious. I loved the way they felt underneath my clothes. Now a year later I had been found out. I was so nervous but I also knew I was a little turned on as well.
Tuesday of that week was when he first contacted me. My mom was working the late shift which got off at 2:00 a.m. Jason called and said he was going to stop by tonight. He showed up a little after 5:00 p.m. and brought some cheeseburgers. He had also brought a little package with him. After we ate he asked me to open it up. It was lingerie from Victoria Secret. He had bought me a pair of black panties with a little rhinestone design on the front and "Hot Stuff" on the back. There was a matching cami top that went with it. I blushed as I looked at them.
I know I probably shouldn't have but when I saw them in the window I couldn't stop thinking how hot you would look in them. He asked me to try them on. I was still nervous but I did it. I went to my room and slipped off my clothes and tried them on. They fit quite well and I looked in the mirror at myself. Wow I thought. A few minutes later I heard Jason knock on the door. You decent, he said. I hope not, he followed and peeked his head in the door. Wow, very sexy, he said very...
He walked over to me slowly and put his arms around me. You're beautiful he said. And with that he leaned in and kissed me. I could smell his cologne again. I breathed it in and him as well. I couldn't believe this was happening. Within minutes we were French kissing and I was thoroughly enjoying his tongue in my mouth. One of his hands had moved to my bottom which he was caressing tenderly. He whispered in my ear. You're a bad boy aren't you. Yes, I whispered. Say you're a bad boy, he said. I'm a bad boy, I said. A panty boy, he said. A panty boy, I said. A queer boy, he said. A queer boy, I said. A boy who likes kissing boys, he said. Yes I said. And I'll bet there are more things you'd like to kiss, he said. Yes I said, Yes... I was so turned on I would have done anything he told me to do. Get down on your knees you bad boy, he said. I did. He slipped his pants down while I knelt there and undid his shirt. I could see he had a good body and why my Mom liked him. He was wearing a light blue bikini.
Pull down my underwear, he said. You need to get comfortable with doing this, he said. I slipped them off his hips and pulled them down. His cock was semi erect in front of me. Stick out your tongue, he said. I did. He then brought his cock to it and ran it over my tongue. That's it he said. I want you to lick it he said. I did and began to lick the head of his penis. It was soft and velvety in texture. He then told me to lick the shaft and his balls. I did. I was so incredibly turned on by the taste of him I couldn't believe it. I knew I wanted to suck him which he eventually let me do. He kept his hand on the back of my head while I sucked and slurped his cock. Every once in a while he would hold my head firmly and press himself into my mouth. This was the hard part as his cock would press against the back of my mouth. One time though he was actually able to push it down my throat a bit. He told me later this was what real girls could do but that with practice boys could do it even better. He came in my mouth that day. He told me before hand that he was going to do it and that I would need to swallow all of his cum and that you should never miss any and that cum was actually packed with vitamins. It was a different sensation that warm sticky cum. I didn't mind it though and was able to swallow all of it. He made sure I licked him nice and clean as well. I was so turned on at this point I was ready to cum myself. Jason told me to get on the bed on all fours. I did so and he got on behind me. He pulled my panties down and reached around and began to stroke me. I began to moan a bit. That's it he, said. Let me hear you. I began to moan a little louder which felt good. Say my name, he said. Jason...Jason... I moaned. Oooooh, yeah. You are so fucking hot, he said. Then I felt his hand right on my bottom, right there. Ooooooooh I said. Oh yeah, that's it he said. I felt his finger begin to swirl around my hole. Uhhhhh, Uhhhhh, I moaned. Oh that's it he said. Say Jason. Jason I moaned. And with that I felt him press his finger against my bottom. Again, he said. Jason, I said as he did it again. Again, he said. And the rhythm began. Each time I felt his finger I said his name. And each time he pressed a little harder. I was coming to climax. Jason, Jason, Jason, Jason and then I felt his finger push fully inside of me and I yelled, Jasonnnnnnnnnn. I came then all over my bed. Jason continued to gently finger me while he stroked me and I finished coming.
Afterwards he rolled me over and laid on top of me and we kissed. He was certainly bigger than me but I liked the feel of his body on mine. He called me his little pantyboy and told me how sexy I was and what a good lover I was. He said he wanted to see me again. By the time he left we had a tentative schedule already worked out. Mom worked late Tuesdays and Thursdays and that he would come over at dinner time on those nights.
That summer I saw Jason a lot. It was hard when we were all three together. I even started getting a little jealous of my Mom at those times. Jason played it cool although he wasn't above a little reminder when we were all three together. There were many times when we had dinner together that I would find his and on my leg below the table or get a nice little kiss goodbye with tongue when Mom wasn't around.
Jason continued to buy me lingerie and sexy outfits. So much so that it became hard to find good hiding places for all of it. Jason's tastes also continued to push me more to my feminine side. By the end of summer I had begun to wear dresses when we were together and even wear a little makeup. The final move was when he had me shave my legs. Thankfully I didn't have a lot of hair and it was pretty light anyway. Jason said it was sexy which I quickly agreed.
By the time I entered High School we had already had full intercourse several times and in several positions. Thankfully Jason wasn't overly big and after a couple painful attempts we finally did it. After which it became more regular with Jason fucking me at least once a week. I loved the way he felt inside of me especially when our bodies were pressed together and we came together. I guess I was really a bad boy after all. It was almost like I was addicted to it.
When I entered High School things changed a bit. School was back in session and I had homework and other activities. I even had my eye on a guy or two but wasn't sure how to even approach the possibility with them.
Jason and I continued to see each other but my Mom's schedule changed that year which threw things off a bit. By the end of my Freshman year things weren't too good between them though and they eventually broke up. We continued to see each other though for another year. Jason took a job out of town at the end of my Sophomore year so it ended OK and I, well, I found myself another beau who liked his boys in lingerie but that is another story.