My First Time – part 2

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My First Time – part 2Seems right that I talk about the second time Steve and I had sex. Don’t worry I’m not going to talk about them all, just some of the kinkiest times we had. The second meet was notable not only for the sex but also I was sort of willingly pushed into a higher level of crossdressing. For a long time I had been wearing panties, tights, stocking etc under my male clothes, when I got the chance. I had worn dresses etc when home alone, but this was different.I got a text message from Steve on the Sunday evening after our Saturday night, saying he had enjoyed himself and did I want to do it it again. Ultimately we agreed to meet up on the following Friday, during the day, back at the house. I was told that if the weather was good we would swim but I should get myself a ladies one piece, pink swim suit to swim in and a matching pair of flip flops. I ordered them on line almost immediately and was super excited about the whole idea. I did grow. more nervous as the week went by. I had loved kneeling between his legs and taking his cock in my mouth but the anal had hurt and I was apprehensive about doing that again. At times I was very tempted to send a text message and cancel.I didn’t though and arrived at the house at about 10.00am as planned. Steve asked me if I had got what he wanted and I showed him the contents of my bag. He took me into his bedroom and showed me some items he had bought. There was a pink, medium sized butt plug, the bottle of lube, some pink nail varnish, pink lipstick and a blonde wig. Facing that lot made me nervous but excited as I had never a wig, nor basic make up. He suggested I get ready, and I stripped down in front of him, he watched me insert the butt plug and then left, telling me to meet him at the pool when I was ready. As he had left, I didn’t see the need to cover myself up immediately so started with the nail varnish. That was awkward to get right as I hadn’t done it before and my hands were shaking but eventually I had me fingers and toes done. Lipstick – I didn’t have a clue but I think I did an ok job. Once I had worked out which way round the wig went, that was easy. Finally the swim suit went on as did the flip flops. I have to say I played for time a bit by sitting on his bed for a few minutes questioning what I was doing. In the end I kind of just thought sod it and left the house and walked down to the pool. Steve smiled when he saw me and I sat down on a sun lounger next to his. It was heaven! We both knew why we had agreed to meet, Steve wanted to fuck me and I wanted to be fucked but we just laid in the sun for a couple of hours and chatted. I was loving wearing the swim suit and enjoyed bilecik escort catching my finger and toe nails as they stood out more having been painted. I felt super feminine! The buttplug was a constant reminder of why I was there though. We left the pool and sat at the back of the house to have lunch which was just a bottle of wine and some cheese sandwiches. We chatted and as the wine diminished Steve asked me if I was ok. I was honest and told him I was a bit nervous as it hurt last time. He admitted he had given me a rough time the previous weekend but promised to make it better this time. So when we had finished and I said back to the pool then? He replied no, I’ve fucked you in that, let’s do it somewhere else. He went into the house and came back with a picnic blanket and some pillows and we headed to a section of garden. The gardens at their parents house were big but at no point, anywhere could you be seen – there were no neighbour’s. It was still a bit concerning to see him lay the blanket out in the centre of an open space though! He just looked at me and you won’t be needing clothes for this bit and I took that as the cue to take my swim suit off. That was the first time I had ever stood naked, outside, Nevermind in front of anyway and my dick started to harden. Steve just pointed at it and said Nevermind yours, work your magic on mine. He took his shorts off and laid down on the blanket with his legs open. As I said in the previous account, he doesn’t have a massive cock but I still enjoyed seeing it again. This time I didn’t just grab it and start tugging I managed to control myself and just rub the tip of it at first but the sight of my pink finger nails holding his cock was getting me extremely horny. After a bit of teasing I held it by the shaft and bent over to kiss the end of it. We then decided to play the game of seeing how much of it I could get in my mouth. Not very much! About the first two inches, but I was more relaxed this time, and less drunk so I was able to give him a proper blowjob rather than just suck the end whilst wanking him into my mouth. I was doing all the things I thought I should be doing like cupping and stroking his balls, using my tongue etc. Eventually he gently pushed my head off his cock and turned me around. He pulled out the butt plug very slowly but it felt good and I was on a blanket with my head in a pillow. Then came the cock. You know, I’ve said it before but anal sex does hurt! And whilst lube helps, that’s just it, it helps! It doesn’t make it nice and comfortable. It was easier this time though, wearing the buttplug for a few hours may have helped I suppose, maybe the fact I know bilecik escort bayan what was coming helped too. He was gentle at times but he did mix it up a bit so when I relaxed he would give me a really hard thrust, or a few in succession, before slowing down again. On the whole though, it was easier and even more, enjoyable. When he pulled out of me, he flipped me over and I was on my back. That was good! Now I was in a position that most women like for their love making. Before I knew it his cock was coming back in. It was kind of weird but sexy lifting my head and looking down to see his cock slide in and out of me. Also a bit strange seeing him above me. As an aside, Steve and I only ever kissed once and that will be in another sharing. We never got romantically involved, the whole thing was just a bit of fun, mainly for me, and lots of sex. This time he didn’t ask me where I wanted his cum, he just said, lift your head and open your mouth and try and catch some. As I did he pulled out and spurted. It didn’t reach my mouth but hit my belly and chest and a glob of it landed on my chin. Whilst it was still painful, I found this second experience much more enjoyable and it kind of gave me a bit of confidence as I knew, if it happened again it would be more like that than the first time. Plus, there’s always that special feeling when a guy comes and you know it’s because of you. The day was over at that point and I had nothing left to do but borrow some of his mums nail polish remover and remove that and my lipstick and get changed back. My anus still hurt like hell for a while afterwards but I like to think I had a glow about me and the memory and feelings of that whole days experience still make me horny, as it has telling you this.Another random experience with Steve. These will be random now as I don’t recall which order they come in really. The rest of that summer was just fuelled by me crossdressing and sex. Much of it was the same as the previous time and there is no point in just writing “I wrapped my lips around his cock and then he pounded my ass”, so many times. So from now, I’m going to tell you something pretty kinky we did, or I did lol and that will be the same for this series of recollections.It was a weekday night, no idea which one but I know it was a weekday as I was leaving the house in the morning, to drive to work. That meant it would have to be an early night 😉 and not too much booze. I didn’t get to Steve until maybe 6.00pm but went straight in and got changed. I remember the outfit well, as it was one of my favourites. Strappy pink vest top, a very short pink, gray and black mini skirt which was so short escort bilecik that it sometimes failed to hide anything, opaque black tights and some women’s Reebok trainers I bought which were black with pink lettering and pink Reebok stripes. To be fair, it was a bit warm for tights, never mind thicker ones, but, those of you that look at my profile and my pics will know that I like nylons and I don’t need any excuse to wear them! I do know that by that time I was ok with make up and I was using stick on finger nails which gave me a longer and more feminine finger nail. If you buy them, the glue on ones are great but only best for long term wearing, as the taking them off is ok, but you get glue residue on your nails which can be a bit of a pain to remove and in my case it needed to be removed to for the girlfriend and work colleagues so on short term meet ups I always used the stick on ones, not as solid but hey, I wasn’t doing house work!I was feeling great in this outfit and we were sat outside on the back patio. It wasn’t late but we were both aware of the time and the fact I needed to change and get the nails off etc, after sex, so I could sleep and get to work the next day. I had already had my hand down Steves shorts a couple of times in the last 30 minutes when suddenly he’s said “I dare you”. To what I said. Stick a bottle of beer up your ass and give it a good shake. WTF? I did a quick thought process in my head and came to the conclusion it wouldn’t kill me. I just replied, get me some lube and a bottle of beer and I will try it. I have never seen Steve run so fast lol, but, likewise, I had my tights and panties down before he got back. He put the bottle on the table, with the opener and handed me the lube. I lubed up my hole and then opened the bottle and lubed it up. When I picked up the bottle Steve told to wait. I might agitate the beer too much by moving it around. We came to the conclusion it might be better if the bottle went onto a hard surface and I impaled myself on it. We went with that and put the bottle on my chair and then I sank down onto it. Is is in he said and I said yes. Hold onto it and stand back up, I want to check. I stood up and turned me back to him while he pulled my ass cheeks apart. Shake and pound yourself with it, he saidSo I did. What happened won’t be for everyone and I advise caution, but this is my experience. My ass flooded with very cold fizzing beer, which was lovely, I have to say. However, what also happened was my bowl was flooded with gas and liquid and in a few short seconds was painfully bloated. It was painful and I just thought to myself that I might die. At that moment the gas and liquid broke the seal my ass had made around the bottle and I erupted gas and beer. That bit was awesome! We all know the anus is very sensitive and the bubbles, oh man, those bubbles! Try it if you dare lol. I do still treat myself to one occasionally.

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