26/05/2019
Last post 3/24. When I was in High School I had a neighbor, a couple doors down, a recently divorced Doctor in his mid 30's, very nice guy, good looking. He traveled a lot and had a really nice house with a pool, and a dog, a male Boxer that he paid me to take care of when he was out of town, I'd go to his house every day to feed and walk the dog, and he allowed me use of his pool. I was at the house one day, and after walking Boris the Boxer and feeding him, I decided to go for a swim since Ron wasn't due back until the next evening, and I hadn't brought my bikini with me, so I just took everything off and skinny-dipped. I did laps for about 20 minutes or so, and was just walking out of the pool up the steps at the shallow end and much to my surprise stood Dr. Ron, back a day early. I think he was as startled as I was, I was completely naked standing probably 6 feet away from a grown man at just 18 years old, I made a feeble attempt to cover up and he made a feeble attempt to avert his eyes, but neither attempt seemed to work very well. Finally he handed me a towel and we both started laughing, then we sat down by the pool, me still wearing only the towel. He apologized for seeing me, but I told him it was OK, and it felt good to be seen by a real man. He asked what I meant by that, and I told him that I'd "sort of" had sex a couple times with my boyfriend, but he pretty much orgasmed immediately after putting the condom on, so I'd never actually experienced intercourse. I felt comfortable talking to him about that, since he was a Doctor, and the discussion then turned to what he'd seen when I walked out of the pool, I looked pretty much the same as I do today, 5'6" 125lbs, 36D breasts, the only difference being that I had a neatly trimmed full bush then, vs a neatly trimmed landing strip now. He told me I was a very beautiful young woman, and that soon I would experience sex as it should be, and he said he felt like a swim too, and he'd go change into his suit, and I jokingly told him since I had nothing on, why should he get to wear a suit? I never thought anything would become of that, but he laughed and stripped naked, and I was basically in awe of his body, I'd been with a boy, but this was a MAN. We both went in the pool for a few minutes, and played a bit of splashing games, then things got more serious as I was jumping up and my breasts rubbed against his chest and he looked at me since I hadn't pulled away. He took me by the hand and led me out of the pool, got a towel and dried me off, then dried himself off, then took my hand and led me into the house and to his bedroom. Both of us just stood there naked for a minute looking at each other, then he asked me if I really wanted to do this, and I told him I did, so then he got a condom out of his bedside table and put it on, laid me on the bed and proceeded to kiss my breasts, moving down to my pussy, then he massaged my clit just enough to get me really wet, then he got on top and entered me. We had sex for well over an hour, and it was nothing like it had been with my boyfriend, it really felt good and I enjoyed every second, he knew my body better than I did. This went on probably 10 or 12 times before I went to College, and he taught me how to use my body to make sex incredibly enjoyable for both myself and my partner.
Fast forward to a couple weeks ago, my boyfriend Dave, also a Doctor, was invited to a 4 day conference in Orlando, and while looking at the schedule of events, my former neighbor and sex mentor Ron was doing a presentation, so I asked Dave if he'd like some company, and since he already knew the whole story of the several times I'd had sex with Ron, he thought it would be fun to re-visit that, and he could witness the action. So, we flew down to Orlando, and as I usually do when I travel, I rented a sports car, this time a brand new 2019 Porsche Boxster S with a 6 speed manual transmission, girl's gotta have fun driving, right, lol?? So, the first day I went to the conference with Dave, I wore a short little mid thigh length tan shirtdress and a pair of tan stiletto heel sandals, tan panties but no bra, very sexy outfit, not revealing but just enough jiggle from my firm breasts to keep them wondering, is she or isn't she? During a break, I noticed Ron on the other side of the room, and I had Dave come with me and I introduced him to Ron, they seemed to hit it off immediately. Ron wasn't staying at the same Hotel as we were, but I told him I'd meet him later the next night for a drink, and to chat about old times a bit. So, after the next days events, Dave and I went back to our hotel, and I took a shower to get ready to meet up with Ron. Dave helped me trim my landing strip perfectly and made sure my legs were silky smooth, then I put on my favorite pair of black stiletto heel pumps, a hot little black mid-thigh length miniskirt, and a very sexy 3/4 sleeve white button-front blouse, perfectly fitted, not too tight or too loose and making it pretty easy to see that I wasn't wearing a bra, and my erect nipples stood proudly to that fact. I put on my watch, a gold bracelet and a gold locket, and checked my look in the mirror, my long bare legs all the way, no panties, and Dave was pretty hard seeing me as well. I grabbed the car keys and my purse and headed off for my adventure. When I got to Ron's hotel, I saw him in a booth on the far end of the bar, and I enjoyed him watching me as I walked towards him and sat down. His first word was "wow"!! and he asked if he was correct in thinking I wasn't wearing a bra, and I told him he was correct, in fact not only was I going braless, I wasn't wearing panties either, and since he was a breast guy and had never seen me dressed without a bra before, this was for him. We ordered drinks and he said he was impressed both by my confidence and my body, then we started to talk about doing something for old times. I told him I'd like to show him what he'd taught me 6 years before, and if he'd be interested if Dave watched us having sex. He was surprised but he said he was game for that, so he paid for the drinks, we walked out to the valet to get the Porsche and headed back to our hotel, as I shifted the gears he put his hand on my right thigh, and I gave him the green light to go farther up, and he smiled broadly when he felt my landing strip, he'd told me way back when that he really liked them. After the 20 minute drive, we got out at our valet and headed up to our room and Dave greeted us. After chatting a few minutes, I was more than ready, so I guided Ron's hand to my blouse and had him unbutton it and take it off, then he unzipped my miniskirt and lowered it down my long legs and I stepped out of it, standing in front of 2 men wearing only my stilettos, then I took them off and got in bed. I told Ron he wouldn't be using a condom this time, as I'd always wanted to feel him cum inside me, and within seconds he was deep inside me. His penis felt fantastic inside me, and we had sex for almost 2 hours in several positions, and he finished in missionary, where we'd started, unleashing a huge amount of cum inside me before he pulled out. Dave came over to the bed and kissed me, then kissed my breasts, and looked at Ron's juices dripping out of me. After a few minutes, I went and took a shower, then put my outfit back on to drive Ron back to his hotel. Ron got dressed and we went down to the valet to get the Porsche and during the drive back Ron told me that was the best sex he'd ever had, and I told him that he'd taught me well, and I'd just wanted to show him what I'd learned, just one time. He got another nice long feel of my breasts and we kissed when I dropped him off, then I headed back to our hotel and my nipples were incredibly hard and erect, after I dropped the Porsche at the valet, I practically ran up to our room, I wanted Dave so bad I could taste it. When he answered the door, I practically ripped his clothes off and threw him on the bed, we had some really intense sex, fell asleep and woke a few hours later for more sex. 2 more days of the conference were left, no more sex with Ron, but lots more with Dave, stay tuned, lol.