Men Wearing Panties, Pantyhose, And Lingerie
Submitted Stories
Title: Family Friend
I started dressing when I was about 7 years old. I did the typical dressing in my mom's and sister's panties and bra's. Around the age of 16 I started buying my own things with the money I made from my job after school. I would usually wear panties and hose to school under my regular clothes and no one knew any different. Well, this one time we had a family friend staying with us whom we called "Charles". He was just an old family friend. He at the time was around 50 years old I guess. Anyway, one day I was in my room trying on some new panties and thigh highs and a slip, when he walked in to ask me a question. I had forgotten to lock my door. Anyway, he looked at me and told me to "get over here right now" so I did. Trying to explain it wasn't what he thought. He just took me and bent me over his knee and started to spank me, telling me that if my parents only knew they would be devastated. Meanwhile as he is spanking my panty covered ass, I start to get hard, and before long I am cumming in my panties and all over his legs. He gets even more mad and says "oh..the little slut enjoys this huh". He then made me lick the cum from my panties and left my room and told me to never speak of this to my parents for they would be mad at their son for trying to be a girl. Two weeks later, after I bought some new lingerie I decide to go into our attic, it was finished and very spacious, to try everything on. I put on my red satin bikini panties and black bra, black crotchless pantyhose and black slip. I am laying down in a bean bag chair rubbing my cock through my panties, when I hear Charles coming down the hallway looking for me. I scramble to hide under the bed we had in the attic, I hear him open the door and walk in. I peer out from under the bed, and I see him picking up a pair of panties I forgot to grab. He calls for me to quit hiding and come out, that he knew I was up there. So I slide out from under the bed, knowing he wouldn't leave until I did. He says "well, well, well...what should we do about this?" He walked over and sat on the bed and said "assume the position" So I lay down across his lap and he takes a firm hand and smacks my pantied ass, and then caresses it after the blow. He says "my your ass feels good in these". I tried to slip away, even though I could feel my erection start to grow, and he lets out with another whack to my ass, and my dick gets even harder. I reach back and try to stop his hand from reaching my ass again, and I accidentally rub my hand by his crotch and he had the biggest hard on. So I just went for it, grabbed his cock through his pants and started to jerk on it. He, quickly unzipped his pants and allowed me up. He lay back on the bed and I dove between his legs. Tasting a cock for the first time, I did my best to devour it. I would squeeze his balls as I would swallow as much of his hard cock as I could. I was in heaven and I didn't want it to end. I could tell he was enjoying it as he would thrust his hips to meet my mouth, and his moans would drive me wild. He finally came, filling up my mouth with his hot, sweet cum. We cleaned up and he asked if we could get together again, and I said how about tonight, say you are taking me to a movie that I wanted to see. You used to do that. So we work that plan out. I get dressed in some really sexy lingerie and we get in his car and head out. He pulls into a construction site, gets out his car and grabs a blanket and we go into a house that is under construction. I get undressed, letting him see me in my beautiful outfit. He takes off his clothes and lays the blanket down on a stack of drywall and I go over and sit down, and he walks up to me and I take his cock into my mouth once again. He then lays me back and asks if he can fuck me, and I said that I will try. And try I did. He slides his cock past my panties and deep into my ass and I am in total bliss. He takes it slow, knowing this is my first time. And as he takes a couple of thrusts into me, I start cumming like there is no tomorrow. He pulls his cock out, scoops up my huge load and smears it all over his cock and then shoves it back into me. Oh it slides in so easy now, and feels so good with my cum on it. He is about to cum, I can feel it and I want it so badly. He pulls out and tells me to get on all fours. This time he pulls my panties down just enough to get back to my awaiting ass. He rams it in me, I let out a loud moan as it just feels incredible. As he pounds me ass, he smacks my ass cheeks in the process, and this gets me even hotter and I start to ram my ass back to him to meet his thrusts. I tell him I want him to cum and he obliges after another five minutes of glorious sex. Shooting deep into me, I squeeze every drop I can out of him. We cleaned ourselves up and went back home. We hooked up quite a few times and just about 5 years ago, his son asked me what his dad meant when he told him that "I was a great person and that he should ask me one day to take care of him like I did his dad".
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