Karupsarchives - Never Lose Your Karups Moms Again

For a long time I've had an attraction to men who dress up as girls, despite the fact that I don't consider myself gay. I don't know what it is or when it started but I just know I find a feminine guy in a skimpy outfit sexier than a girl with a skimpy outfit. I still might find the girl attractive but for some reason I'd rather have the outfit on the guy. When I was in my freshman year in high school, I got along normally with my peers. I talked with girls, and made some guy friends. Well one day a schoolmate of mine caught my eye. Freddie Simmons. He was kind of smaller than me, slim, and was very feminine. he had brownish hair and the style where it covers a bit of karupsha his eyebrows I first saw him walking the courtyard while we were headed to our next period. He was tying his shoe on one of the benches. Originally I looked over his way because I thought I heard one of my friends. I know its not fair to judge hot amateur pics someone on their looks but i guessed he was gay. Just the way he stood up from the bench was kind of feminine. And the way He ran was sort of girlie. Not that I hated him for it, I just thought "Huh. A gay guy." So a few months go by with no contact with him until the school was auditioning for a play; Seussical The Musical. I wanted to audition because i like acting, and there I saw Freddie. After the audition period and a few rehearsals, we talked to each other for the first time. I was sitting backstage and after he was done with his scene he was looking for a place to sit and since i had enough space on the bench i invited him over. We talked for a bit and we really hit it off. After some more rehearsals, we started hanging out outside of rehearsals. There was bowling alley close by and we usually go there to hang out with some of xxx amateur pictures our friends. I could tell he liked me because he was always lightly touching me, like a playful shove here and there, as well as hanging out with me rather than his other friends. One day he asked me if I was gay or possibly bi. I said i wasn't and he just said "Oh. Ok." then got quiet. After we got our costumes, we went to the changing room, and i didnt notice it the first few times we dressed but I looked Freddie's way one day and saw some light pink fabric hiding in his pants. My interest in him reached a whole new level. I went up to him when we were alone and asked "Are they making you wear girlie underwear?" he responded with "No. Why?" i just said i was curious and went back to putting my socks on. He then said "You saw them didn't you?" I nodded and he had a complex look on his face. After he sighed, he told me he liked the feel of woman underwear and would sometimes wear them. I told him it doesn't bother me. I didn't tell him that i wanted him to pull his pants down and show me his cock pressing against his panties for obvious reasons. I asked him if he put on other woman clothing. He told me he does sometimes, when hes alone at home. I told him it would interesting to see him like that. He said he wasn't comfortable showing other people. Only his best, best friend knew. I said I understood and left it alone at the time. But every now and again I would lightly bring it up in conversation. After I learned this, I came up with a plan. I told him I felt uncomfortable about how i presented my character on stage (im just playing a monkey, btw) and said i wanted his karups hardcore opinion and asked if i could come to his place. <:) he said yes. So on the following Saturday we went to his place. He introduced me to his family, they said it was rare for Freddie to bring a male friend home. We went to his room and started rehearsing. Took a break and he went out cause his mother needed him. While he was gone (finally) I took a quick look through his drawers. in his underwear drawer i saw male underwear which took up about / of the drawer and his panties. My imagination went wild thinking about his cock peeking out of his pink laced panties. Or seeing it through his black panties. i then closed the drawer and was curious on what else he had. at the bottom drawer i found a few dresses and some skinny jeans. I closed it up and went back to where i was sitting while freddie was none the wiser. "I wanna see him wear them" I kept thinking as the days went by. I went over to his house as often as I could and spent the night everytime i was asked. Every night out conversations got more intimate. We discussed past relationships and i could tell he really wanted to go deeper with out relationship. Unfortunately i only found his trap side more appealing. I never told him this because i thought it might bother him. one day i made up a story on how my mother was gonna hang out with her old friends. i told freddie that i would go bored if i was just by myself and asked if i could spend the weekend with him. he said yes. I didnt suggest my place because i had a plan. after arriving to his place, i told him i ddint feel comfortable about my stuff taking up space since someone might step on them. so i was gonna stick some clothes in his drawers. before he could stopme i opened the top drawer, got a quick peek, and he closed it shut. I acted a little shocked while he was embarrassed. I told him i didnt mind and that some people have their own fetishes. Like me wanting you put on your best trap outfit, while i pound you in the ass. HURRY UP AND CROSS DRESS DAMMIT!!! he just said under the bed should be fine if i left it in the bag. after a while i told him i really dont care about whether or not he cross dressed. after hearing this a few times he believed me and looked relieved. I felt like i was finally getting somewhere and being the honey teenager that i was, i told him i was curious on how he looked. he of course was against it, but i kept pushing and pushing until he gave in. he grabbed some clothes and told me to wait. he went to his bathroom and after about minutes he came out. he didnt have makeup or a wig on. what he put on was a light white short sleeve shirt and those skinny jeans. i said he didnt look to bad and he should have more confidence in womans clothing. he did look more attractive but what i wanted was for him to put on his wig he said he had. I told him to try it with the wig. then he grabbed it from the closet and went back into the bathroom. after a while he came out wearing a straight haired, black wig. Again, told him it was great. I asked if he was even wearing the panties. he told me he was and gave me a quick peek. god did that drive me crazy. first night, nothing happened. second day he didnt wear the womans clothing, toward the evening time i asked him why and he just said he didnt feel like it but he still wore the underwear. I said "Thats a shame since you're..." did that on purpose. i was nervous about calling another guy cute but i also knew this was a good way to tell him while acting really embarrassed. He of course wanted to know what i was gonna say and i "reluctantly" told him i thought he looked really cute. He was a little embarrassed and asked if i was serious. I of course said yes i was and after a while of silence he got up, grabbed some clothes and the wig and went to the bathroom. I hear the shower go on and after almost two hours, he comes out with wig, eye shadowing, light red lipstick, and of course, the wig. He had on a light green sleeveless shirt with a little hole on the top and some shorts. HOLY! GOD! A real life trap was right in front of me. I bet if i made some clothing requests, he would follow them. i was just to stunned to think. I mean here before me was a real life, cute, trap, wearing girly clothing and some perfume. I was in shock. Of course i had to play it cool. Its a first for me too. The rest of the day he wore that outfit. it was getting late and we went back to his room. He jumped face first on the bed, while i admired his legs. I said "You seem to be in a good mood" He told me of course he is. He never showed that to anyone but his best friend. "I told him he should have more confidence in that appearance. He then sat up and looked down and told me he loved me. I was taken aback by this. I just responded with "Huh." he looked up at me. i was of course standing up and him looking up at me with those eyes nearly made me take him right then and there. He then stood up and walked toward me and said it again. after being in front of me he nervously touched my chest and moved his hand up to my face. He then moved my face and his face a bit closer. He gave me a light kiss and then i gave him one back. he stepped back a bit and then i stepped forward. i grabbed his shoulders and gave him a deeper kiss. he wrapped his arms around me while we continued to kiss. i slid my hand down to his skinny body and groped his chest a bit. i played with the nipple a bit and pulled away from his face. he looked really flushed and was breathing heavily. i knew he was nervous and that was causing him to be short on breath but i found it incredibly sexy. i kissed his neck a bit and went down to his shirt while i made him sit on the bed. i went further down to his belly and pulled his shirt up so i could lick his nipples. he then took the shirt off and was beginning to pull mine off. after i got it off i kissed him for a bit and laid him down on the bed. I asked him if he knew where i was going with this. He nodded. I asked if he was okay with, it while i rubbed my hard cock on his and he nodded. i then started taking my pants off while he did the same. I was reluctant to take my underwear off then finally did. he was about to take his panties off and i told him to leave them one. he asid ok and then i continued to rub our cocks together. the fabric felt incredible, especially with two hard organs rubbing against eachother. after a while of doing this and kissing i moved his panties down a little. i didnt take them off. i left them on one of his legs. i tuned him over and was ready to go in when he stopped me. I was confused and a little angry and asked him why we stopped? he said he didnt feel clean enough and wanted to take a shower. i came up with some middle grounds, because there was no way i could just stop now. i suggested we both get in the shower. didnt take long for him to agree. we went in to the shower together and after turning it on, we started making out again. i turned him around and he stopped me again and told me he wanted clean in there. feeling a bit dirty i told him i know a great tool thatll get in there and start cleaning. he chuckled and agreed. so he bent over and i was trying to stick it in but it was too tight. i only got the tip in and felt uncomfortable. i then grabbed some soup and put it around his anus and stuck some on my penis. it slide in a little more but i couldnt go too deep because it still hurt him. but the pressure i felt was incredible. i only did a few strokes and came inside of him. i felt bad after wards since he wanted to do the same with me and i said i want comfortable with it. he suggested, sucking it, jerking it, but i wimped out. after giving up the idea he started cleaning his ass with his middle finger. he went in and out and i envied his finger. it looked nice. almost made me want to receive anal. i asked him why he was doing that. he said, "Who knows. The night is still young." while giving a little smile. i wouldve given anything to get a boner then but i just came so not gonna happen. i got out of the shower first since i finished what i went in there for. he came out still wearing the wig and the towel over his waist. he looked so good with that wet wig. i stood up and started making out with him again, hard. i pressed him against the wall and lightly pounded our dicks together while he wrapped on leg around me. he dropped the towel and i picked him up and threw him on the bed. i got on top of him and frenched him hard. my cock was pressing against his. i could feel it twitching against mine, just as mine was twitching against his. i asked if he wanted to go again and while out of breath he gave the sweetest "Yeah." i then turned him over and after i did he said wait, and got up. he went to the bathroom upstairs, the ones his parents used and brought back some baby oil. put down some towels, stuck his ass in the air and told me to put it on. i lightly put some on his asshole's entrance and actually put some on my finger and put it inside him. i then applied some on my dick. Slide right in. it was still tight but not as bad as it once was. i lasted longer and was able to go deeper. i think he was till in pain but he didnt say anything while stroking his cock. i started a bit slow and sped up as i felt my climax coming. his toes curled up and he was biting and gripping the towels hard. i knew it was hurting but that view only turned me on more. after speeding up i came so hard in his ass. i thrusted in a few more times before i was done. i then pulled myself out and laid on the bed while he finished jerking off. we cuddled a bit, joked a bit, got dressed before we went to sleep and reluctantly moved from eachothers arms. we had school the next day and didnt want to risk getting caught by his parents. he of course put the baby oil back, came back and changed and went to bed. i couldnt sleep. i wanted to go again, but didnt wanna bother him. i hardly got any sleep that night. honest_here