04/10/2019
Just after I finished helping my 18 year old virgin friend Kyle experience the pleasure of sex, we both made a trip to the bathroom to freshen up a bit before getting some sleep, he went first, then came back to the bed and I took my turn. I don't like walking barefoot in hotel rooms (never know what's on those floors, lol) and since I'd forgotten to pack my slippers I was using my high heels to make my way around, so I put them on and did my thing, then came back in the bedroom, wearing only the stilettos. Kyle really was enjoying that, saying that he was really turned on by well toned, long legged girls with big boobs, exactly my build, but I reminded him that after the sexual experience we had just shared, only an experienced woman could have provided that to him. I noticed that he had put his boxers back on, and I laughed as I got back in bed beside him, and told him if he was waking up next to a naked woman, I'd better be waking up next to a naked guy, so he took them back off and we snuggled together and fell asleep. No alarm the next morning, my last day in Orlando was a free day, and I awoke to find him kissing my breasts, a nice way to wake up. Then he laid beside me and faced me as he rubbed my landing strip, and I was telling him about my boyfriend David, he seemed a bit confused and I explained that it was with Dave's blessing, he found my sex with other men a real turn on, as long as I told him everything. he asked if David knew he had spent the night with me, and I thought for a minute that I'd told Dave we might have sex, but I hadn't given him the details yet, and I said let's give him a call right now and you can meet David. He looked a bit uneasy as I called the number and Dave's face came on my laptop screen as Kyle and I laid naked on the bed. I put the laptop in a position that Dave could get a good view of us in bed, and introduced Kyle to Dave, Kyle still seeming a bit uneasy, but Dave calmed him down pretty quickly by asking how he'd enjoyed having sex his first time with a sexually confident and experienced woman instead of an equally inexperienced teenage girl. He told Dave it had been incredible, and Dave said that he knew it would be, because I was always great in bed. Kyle was by then very much erect, and I grabbed his penis and asked if he was ready for another round, and if he'd mind if Dave watched us in action. Before he could answer I pulled him over on top of me and rubbed his erection on my clit as I spread my legs, and I told him to go nice and slow. He slowly pushed deep into my pussy and I asked him to just lie there for a second and I asked Dave if he could see everything, which he said he could, then I began moving under Kyle as he began to slowly thrust into my tight little pussy, I'd created a sexual monster, Kyle was really doing a fantastic job making me feel really good as we went at it. After about 20 minutes we were both ready to come, and Kyle released a fountain of his cum inside me and we both climaxed. We laid there for a minute, I'd locked my legs around his back as he fucked me, and I lowered my legs back down and Kyle pulled his penis out of my pussy, followed by a very nice stream of his cum. Dave had watched the whole thing and he was pretty aroused, only saying "wow" when he saw Kyle's cum dripping from my pussy. He told Kyle that he'd have the girls coming back for more and that I had taught him well, Kyle thanked him for allowing him to have sex with me, and that he thought I was the hottest woman he'd ever seen, even in pictures. After a couple minutes talking with Dave, we ended the call, Kyle was lying beside me on his back, and I just felt like going again, so I climbed on top of him, put his hands on my breasts, and lowered my still very wet pussy onto his still very erect penis, and I rode him for about 10 minutes before we both climaxed together again, with another load of Kyle's cum shooting deep inside me. I got off him, put on my stilettos and went into the bathroom to take a shower, and when I came out Kyle was sound asleep, so maybe I'd been a bit too much woman for him, but really he'd been a real stud, especially since it was his first time having sex. I wanted a cup of coffee, so I put on a pair of VS bikini panties, a very short pair of Daisy Duke cut-offs and a plain white T-shirt along with my stilettos, left Kyle a note then went down to the lobby to get us both some coffee and a Danish. A couple businessman types there obviously enjoyed the look of the Daisy Dukes, fuck me stilettos and the braless T-shirt as I fixed 2 cups of coffee and put both cups and a couple Danish on a small tray and headed back to the elevator. One of them asked if I was really hungry, and I laughed and told them the other was for my guy, he was pretty tired, and that I thought I'd worn him out. The guy said "I bet he enjoyed being worn out" and I thanked him and back upstairs I went. I got back to the room and Kyle was still asleep, so I woke him by tickling his penis a bit. Once awake he looked at how I was dressed and asked if I'd had room service, and I told him no, I'd gone down to the lobby to get it myself. He said it looked like every guys wet dream and asked if any guys had seen me, and I told him there were 4 men down there and myself, so yes, they had seen, and appreciated my little AM show, lol. I turned on the TV and sat down to have my coffee and Danish, and told Kyle to join me after he showered and we could plan the rest of the day. To be continued...