First time speedo sex

Over the last few post I have been exploring options with my girlfriends partner James ( which there is a speedo story to cum with him) however there have been a few encounters in the past before James that I will share with you. My first speedo encounter with a guy happened whilst I was holiday on a off Queensland, this was almost 8 years ago. ##It is a long story but the end is well worth it## It didn't start out as me meeting a guy as such, but I will fill you in with a bit of background info As it turned out I met a nice girl getting onto the boat transfer on the way to my island holiday the only reason I took an interest she was wearing wet look leggings, I wasn't the only guy that was checking her out but she sat next to me ( lucky me). On the ride we got chatting about different stuff we introduced ourselves (I think her name was Rebecca off memory) and I kept checking her lovely body out, as she was looking very sexy. I was beginning to get a small bulge in my shorts which she would have had to notice but didn't say anything. The first couple of days were uneventful, till I bumped into Rebecca again she was returning from the early gym workout, she looked just a sexy in her black spandex leggings. She noticed me checking her out again and said " Are you getting a good look" I was shocked and apologized for staring at her. She was joking and asked me if I wanted to join her for a swim, once she got changed. We went into her room, and she started to remove her sweaty clothes and with no time she was naked. She popped into the bathroom for a quick shower, meanwhile I am sitting on the bed with a erect cock in my shorts. She came out and this time she did notice the bulge and asked me to remove my shorts. I stood there in my speedos with an erection, she then proceeded to remove them and began to play with my cock. Now the story gets even more interesting because she then proceeded to put hair removing cream on my pubes to make me bald. This was a little strange as she thought it would be fun. Once the cream had been removed she told me to go have a shower to rinse off, she followed me into the bathroom and then into the shower. She then proceeded to go down on my cock and give me a blowjob. She was very good and didn't use her hands only her mouth. After only a couple of minutes i told her I was about to cum and she just kept going, The feeling of exploding down her thought was intense and and took every drop. After we cleaned up she told me that this was her last day there and she wanted to make it enjoyable. I was just about to put my speedos on when I accidentally bumped her suitcase was opened on the floor and having a quick look I noticed assortment of spandex clothing. She told me that it would only be fair that she could check "me" out in a pair of her leggings and was there any that took my fancy, I picked her wet look leggings. I started putting them on and my erection came up again, They were a tight fit but felt amazing. She then told me to put my shirt back on and walk out of the room and around the pool, I said arent you going to put something on, well she might have just walked around naked as she wore the smallest thong bikini imaginable. It was very arousing I wasnt allowed to hide my bugle or erection if I wanted my reward. The walk lasted about 15 minutes and we got back to her room she then proceed to stripe me again and told be to lay on the bed, and not move until I make her cum she then proceeded to "ride" my cock until she came, but wasn't allowed to cum myself which was very hard after about 5 minutes she exploded and I told her that I was very close she got off and made me lie there till I relaxed. Rebbecca asked me if I had anal sex before and I told her that I hadn't but was willing to try. She then told me she wanted me to insert my cock up her ass. She lubed it up very well and said to put it in slowly, I was getting very close to cumming and she said she wanted to feel the hot cum up her ass, my cock then let fly with spurt after spurt of cum. It is amazing how an afternoon goes by when you are having sexual pleasures. Rebecca left the next day and I thought that would be the end of my adventures till Tim came along Little did I know that when I did my walk of pleasure in the wet look leggings there was a guy checking me out. It was a couple of days later when I was relaxing by the pool when I noticed a guy coming out of the gym wearing a pair of skins and a tank top and thought that after wearing wet look legging how a pair of them would feel on. He causally walked past me and i thought nice and gave him a smile. I noticed him return to the pool, and put his stuff down on a chair a couple up from mine. When he took his towel off he was wearing a navy blue thong. As he dived in for a swim he noticed that I was checking him out, I watch him get out of the pool and my what a view with the thong up the ass crack. After a while he then moved to the chair next to mine, to my surprise he then introduced himself as Tim and started talking about how good I looked in speedos and the leggings. He noticed that my bulge was getting bigger, and I said it was because he was wearing the skimpy outfit. What took my surprise was he suggested that I might want to try a pair, so he invited me back to his room to view what I might like. I had taken my speedo off and was looking over the the tiny outfit that Tim had put down on the bed .I had never been naked infront of another guy but it felt really comfortable and strangle I wasn't nervous. He liked the fact that I was bald downstairs, and after explaining how it happened he enjoyed me telling of the sexual pleasures Rebecca had done. He suggested that we could try some more if I was up to it. As I was already naked I proceeded to take the thong off Tim and admire his bulge, which he was blad as well, I started playing with his cock and balls first in my hands and then in my mouth. I was going up and down on his cock very slowly which I could see that was turning him on, as I was doing this he started to stroke my cock and at the same time we turned onto the bed to a "69" position and stated sucking each other. It didn't take me long to get that feeling like I was cumming and Tim wasn't far behind. I had also never actually swallowed cum before when tim yelled that he was cumming I just put my lips around the base of his cock and started to swallow, that tasted so sweet as I was swallowing I started cumming in Tims mouth and he swallowed as I pulsated. We relaxed with a drink for a while and he asked if I had tried any other sexual positions after Rebecca. He asked if I would like to try anal sex I was willing to give it a try. It didn't take long before his cock was hard again and I told him that I wanted it deep in my ass, he proceed to use extra lube and go slowly so it didn't hurt. It felt fantastic having something shoved up my ass it didn't take long before Tim got the feeling of cumming so I told him to stick it up the till he explodes which he did. He asked if I wanted to return the favour so we swapped positions and he told me to pound it hard and fast, which only took a minute before I was cumming as well. We ended the afternoon session of sex and went back for a swim, with the black thong Tim gave me to keep as a small reward for being good, he was checking me out whilst we swam for the rest of the afternoon. That was the end of the holiday but one I will never forget. So that is the prelude to the adventures with James and why I felt comfortable around him as I never let on that I had had sex with another guy