My family and I moved to Eastwood when I was 15. The day we moved into the house I meet my first friend in the area Kevin who lived a few houses down. Fairly quickly we became fast friends and started doing all the usual teenage guy stuff together. After a few weeks of knowing each other I was hanging out with him a lot since it was summer and we had quite a bit of time on our hands. I met a number of other friends, but he quickly became the definition of best friend.
There were two great advantages to hanging out with Kevin. First his parents worked all day so we could hang out at his house and not bother anyone. Second he had a sister a year younger than him, Gina. I found Gina very attractive.
Having the run of his house to ourselves every week day for the summer meant we could also get up to some other teen guy stuff. Unlimited internet porn, FTW! We spent quite a bit of time at his computer checking out all the porn we could. I typically left his house pretty satisfied having “relieved” myself several times. After a few days of these activities Kevin wasn’t even shy about pulling it out and taking care of business without leaving the room. It took me a few more days, but I got to the point where I was like, “well, what the hell”, and followed his example.
As this continued he started putting together “reels” of entertainment ahead of time. We didn’t even need to search in between, just let the media player move from clip to clip automatically. This made the whole thing much more exciting since there was no down time, just constant entertainment.
As days went on the nature of the clips began to drift in subtle ways. The focus of the clips moved from less focus on the girls to more on the guys. There would occasionally be a guy on guy clip. The videos were less girls getting fucked and more guys getting blow jobs. There would be occasional guys in girls clothes. Finally the reason for the change became clear one afternoon.
We had settled in for the day’s “reel” and a pretty good video of girl taking it in doggie position while also sucking another guy’s cock was playing. I was just un-zipping and taking out my cock. Instead of the usual unzip and pull out for the masterbation activities, Kevin stood up and pulled off his shirt. Under the shirt he was wearing a lacy blue and mesh top. He pulled off his shorts and was wearing a matching set of panties. His stiff cock was clearly visible through the mesh of the panties. Now I knew about crossdressing guys, we had seen a few videos of them so far, I just wasn’t expecting Kevin to be one of them. Moreover I wasn’t expecting to find the fact that here was Kevin in lingerie to be interesting.
“Ah..well that’s, um different” I said
“yeah , you think so, I raided my mom’s drawer before you got here” said Kevin
“Um yeah, actually it kinda is, is this, ah new” I asked, excitedly aware that my cock which had dropped at first at the surprise was now stiffening, more than it had watching the video.
“Not really I’ve been playing in her drawer for a couple years, gets me really excited and hard” Kevin said “I finally felt comfortable letting you in on my secret…is that cool? I guess maybe since you didn’t jump up and yell what the fuck and run out the door?”
“Yeah, yeah..it’s cool, a little surprising maybe, but cool.” I said
“Your cock seems to agree, I’ve never seen you that hard dude. I was gonna ask you if you wanted to try this, but you don’t seem to need any encouragement.” said Kevin
“Ah, no I guess not” I said looking down at my steel rod hard prick. I have to admit I’d moved from finding Kevin in lingerie interesting to exciting. I also found the idea of trying it myself to be an exciting idea as well. Two additional thoughts occurred to me now as well. One that I hadn’t been aware Kevin had been checking out my cock previously. Second that I was finding his cock really interesting seeing it through those panties. I had never checked out his cock out before, but now that I saw it, it was definitely interesting.
“Still I…I might want to try putting something like that on, ah..when I’m not this excited and I can maybe fit in them better” I said.
“Awesome man, seriously you’re a little smaller and Gina has some stuff I think would be great for you” said Kevin.
“You’ve…been thinking about this for a while I guess?” I said
“Yeah, yeah I kinda have, I was wicked nervous about, well you know taking this step and…”
“No, I get it, it’s cool I’m glad you did, it’s sort of flattering, I guess, I mean I never thought before anyway about…”
“Yeah I get what you’re saying” said Kevin
“Yeah I hope so, because, let me just say it I really want to rub one out just looking at you right now” I said “but ah maybe, you could take your cock out?” I asked.
“Sure, yeah absolutely” said Kevin peeling down the front of the panties he was wearing and letting his cock free. It unfolded and sprang to attention quickly. He was a little longer and thicker than me. “But ah, I was kinda wondering if I could maybe help you get off, if that wouldn’t freak you out too much”
“What like give me a hand job, sure that would be cool” I said
“Well actually I was thinking maybe I could suck you off, I’ve been watching some videos and…” he started
“Ah..yeah sure..yeah, um OK.” I said, I’d gotten a hand job a couple times before from one of the girls at school, but never a Blow Job. I always wanted to try it, so I wasn’t going to pass up the opportunity.
Kevin had me strip naked and lie on the bed. I got comfortable, and then he climbed on to the bed as well. He took a reverse position next to me slightly by my side. I had his feet near my shoulder and was staring at his bottom from behind to the side. Thinking back Kevin had a very nice round bottom. Kevin didn’t waste anytime once he was in position he immediately began licking my cock. This felt amazing as he went up and down it stopping and swirling his tongue on my cock head each time he got there.
I closed my eyes and relaxed into having my cock worked by Kevin’s mouth. I put my hand on his ass caressing it. I imagined it was his sister Gina working my cock. This was a very exciting fantasy, as I thought Gina was crazy hot. As Kevin’s work continued I was getting insanely turned on, I’d never felt this hard and turned on in my life. The first time my cock went in Kevin’s mouth and I could feel his lips near the bottom of my shaft and my head rubbing inside his mouth I nearly blew right away. The warm wet feeling around my cock. Then Kevin pulled back up, with a gentle sucking as he did so, he lingered and sucked extra hard on my cock head. He pulled extra hard and bobbed on it a little. It felt so good I could feel the pressure build in me to blow my load. Then Kevin released and swirled his tongue on the head again.
“Do that again and I think I’ll blow” I said half warning him, half encouraging him too.
“Yeah, that as good?” Kevin asked
“Oh yeah” I said as I felt my cock going back into his mouth. This time as he did the sucking on the way back up, as promised my cock twitched and I blew my load in the most amazing and hard orgasm I’d had in my life to that point. I’d had what I thought were some great ones jerking off, but this made them all seem weak. I grabbed Kevin’s panty covered ass as I blew my load into his mouth.
“Wow, dude that was a lot of cum” said Kevin as he let my cock free of his mouth.
“Yeah, I’ve never cum like that before, that felt fucking amazing” I said after I’d caught my breath and could think again.
“I guess those videos I watched paid off”
“Fuck dude, I feel like I oughta get you some release, from my angle your cock is looking like it needs it” I said
“Yeah that would be awesome, but I’m cool for now. I really want you to try on some of Gina’s stuff if you’re willing, I think that would really get me turned up” said Kevin sounding crazy excited about the idea.
“I don’t think I could say no after that, and I think my cock will fit now” I said looking down at my shrinking member. Kevin’s cock had shrunk a bit now that we were not engaged in our activity. He tucked it sideways back into the panties.
We went to Gina’s room and Kevin opened the top drawer of her dresser. I pulled out a pair of red and orange bikini style panties. He closed the top drawer of the dresser and opened the next one down and now pulled out a red bra with the clasp in the front.
“Here man try these on for size” said Kevin.
I took the offered panties and bra and we went back to Kevin’s room. I first put on the panties. The material as soft and stretchy, I found out later that they were pretty much spandex. The panties felt amazing as I put them on, and once I had them on they were so comfortable and made me feel sexy. Next I put on the bra. I wasn’t sure how I’d feel about it at first. Once the clasp was hooked and straps adjusted, it made me feel even more sexy. I’d wanted to get into Gina’s pants since I meet her, but this wasn’t what I imagined. The feeling of it made me feel like I wanted to satisfy Kevin’s desires as his little slut.
“Whoa, that really turns me on” said Kevin.
“Yeah, good because having it on is making me hard again, and like I really want to play with your cock now.” I said
“Good, because I feel like I’ve got a huge load trying to get out” said Kevin
“Cool” I said as I walked over and pulled his cock out of the panties and started playing with it. I felt him get hard in my hand. I was using my other hand to caress his balls through the panties.
I was about to get on my knees and try sucking his cock when he spoke up and asked me to do something else.
“Hey, I wanna try something it’s ok with you” Kevin said
“Ah, ok, well what is it?” I asked.
“I want to try dry humping your butt, kinda rubbing my cock in your butt through the panties” explained Kevin
“Ah sure, why not” I said actually relieved. I wasn’t really sure how to give him a blow job, I was going to follow his example basically, but I hadn’t watched the activity as much as it seemed he had. His request seemed easier.
“Cool, I didn’t know if you’d go for that, sweet that you will” said Kevin
“So ah, what do I do, how does it work?” I asked
“Well there are a couple ways I’ve seen, but what I wanted to try you just lay on the bed on your front with you legs out wide and I do the rest.” said Kevin as he took off the panties he was wearing.
“OK” I said getting on the bed is the requested position.
I felt Kevin climb onto the bed behind me and then I felt him pressing against my bottom. I could feel his cock pressing into my butt crack as he stroked up and down it slowly. After a few minutes the stroking changed, he was now going up and down along the bottom of the panties, and I could feel the head of his cock touching and stroking my nut sack. I can’t say I hated that sensation. He changed back to stroking up my butt crack, but more quickly this time. I heard him grunt and “ah” and then I felt his hot cum wetting my butt crack and shooting onto my back.
“Uh, awesome man that was so great thanks for letting me try that” Kevin said as he got off of me. He grabbed a tissue and wiped the cum off my back.
As I rolled over I saw the door at the end of the hallway open through the door of Kevin’s room. I felt a moment of panic as we were in what can only be called a compromising state. In through the door walked Gina. I froze totally freaked out now.
“Hi Gina” said Kevin as she walked down the hall. As she walked she unzipped the large shirt she was wearing, which I only realized later was a swim cover up. As the shirt opened I could she was wearing a two piece bikini underneath. Gina turned at the door of her bedroom and went into it, closing the door.
“Fuck! Man! Fuck! She saw us.” I whispered
“No worries, it’s cool, she’s got no problems” Kevin said
“What?” I said with a whispered yell.
“I said no worries Gina’s cool, just chill, it’ll be ok” Kevin said
The door to Gina’s room opened, she walked out in a bathrobe and came into Kevin’s room.
“So he finally went for it and talked you into it” Gina said as she leaned against the doorway looking at us. Gina continued “He’s been talking about trying it for weeks. You’re like his favorite masterbation fantasy after ScarJo.” Gina saw the shocked look on my face as she said this. “Its cool really we have no secrets around here, we even masterbate together. I use his cock for inspiration, he uses my tits, ass, pussy…you get the idea. You look good in my panties and bra, I thought you would, I picked them out for you, you know. If you, ever want to see them on me, or ummm, get me out of them, let me know” Gina finished as she started turning away.
My cock had been rock hard when Kevin, finished humping my ass, it had fallen when Gina first came in and I panic’d. Now with Gina’s statement I was rock hard again.
“Uh, wait Gina, um maybe we could all fool around together” I suggested.
Gina turned back toward us, pulling the belt of the robe.
“I was hoping you’d say that” Gina said as the robe opened and she shrugged it off her shoulders. She was wearing a pair of panties just like the ones I was in except purple and blue. The blue bra she was wearing was also the same style as the red one I had on.
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