My Flat part 1

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My Flat part 1So, about a year after the summer with Steve, it’s my turn to go to University. I wasn’t sure I wanted to go so after my A levels worried for a couple of years but then decided it would be better to go. I got myself on a 3 year degree course at a local university and my wealthy parents made of their rental properties available for me and they were paying the bills, to save me getting into debt. I moved out of home and into the apartment a couple of weeks before my enrolment. Having my own place had a disadvantage in that I was on my own so not great socially but of course the major advantage was that I could crossdress as often as I wanted, and I did!Uni started and met some really nice people and started to make some friends. As I was in a place where no one knew me I took the step to joking the LGBT society. It was a bit of a shock when on my first social night with the society, I found one of my new friends there too. We had a good night and it strengthen our friendship. We spent a lot of free time together, mostly drinking, as student do. We did a lot of talking about our sexuality no I told him about my crossdressing and the time with Steve. He didn’t really understand it. He was definately a “giver”. One time I remember him saying “so, for you, sex with a guy means you suck him off, let him stick his cock in your bum, which hurts and your reward for that is that he fires his sticky goo in/on/at you? Then he walks away with a smile on his face while you are left a stinging bum hole and having to clean yourself up”. Erm, yes, that’s pretty much it but I love it! As I said to him, if he wants to get into a gay relationship he may have to compromise because a future partner may want to do the same to him occasionally. Still, he wasn’t keen on the idea.A few weeks into the start of the term, we had a Saturday night out planned with 4 or 5 other friends. It was going to be good – lots of drinking and then to a nightclub. Charles (yes, he was quite posh) came over to mine in the morning with a change of clothes for the night. We didn’t really know what to do and basically ended up in the pub when the doors opened at 11.00am. By mid afternoon I was feeling a bit worse for wear and said I wanted to go home and try and sleep off some of the booze before we went out,, so we went back to mine to crash for a bit. We were chatting in the lounge when he said to me that he had never had sex before and that he was scared to as he didn’t know what to do and didn’t want to mess up. I said to him that the act itself is fairly instinctive so it should come naturally. He wasn’t convinced and just said he wasn’t sure and felt quite frightened by it. Then I did something very stupid, basically I offered it him right there, on a plate. As soon as I said it I regretted it. It’s not really wise to try and and involve sex between friends. He looked a bit shocked so I quickly tried to explain my thinking “look, this is the way I see it. We are friends right? We don’t have to call it sex, we can call it larking about, there won’t be any kissing. If we do it doggy we won’t have to look at each other. You get to have some experience with someone who is understanding to your situation which means you won’t be nervous next time karaman escort with a partner, it’s a win for you. It’s win-win as I get to dress up and be fucked. He said he wasn’t sure about me dressing but I made it clear that that was not negotiable and if he wanted to have his wicked way with me then was wanted to dress up for the occasion. So, how is it going to work he asked. Basically, you say you want to try, I am going to text Amy and tell her I can’t make it out tonight and then I’m going to pour myself a glass of wine and go out on the balcony and smoke a couple of cigarettes before jumping in the shower to sort myself out and then get dressed, I will meet you back here and we will go from there. Silence! It felt like an age and I was very nervous in case he just walked out and our friendship would be over. I liked our friendship and was never looking for it to go anywhere, I was just trying to help him out. After what seemed like forever, he said ok, but I’m really nervous. I sent the message, got my wine and went back to the lounge and told him to help himself, if he wanted to some. Then I asked him how big his cock was – 9 inches but quite thin. Don’t be nervous, mine is half that, I said, so there’s no need to be intimidated. I went for my cigarette.I showered and gave myself a good clean out (unscrew the shower head and use the pipe to flood me out, expell and repeat 4 or 5 times). I moisturised my body and let everything dry out, before getting dressed. My first thought was to wear pink but I needed Charles to get an erection so decided against going too girly and went for sexy but more conservative black. False boobs in a black bra, Lacey panties, suspender belt, stockings and a mid length black dress, heels, a bit of make up, wig and false nails. It was a bit of a compromise really, I wanted to feel feminine, so that I could have a good time but was aware that Charles was attracted to other men. When I returned to the lounge I saw Charles out on the balcony drinking and smoking. I walked out to him and he heard the sliding door and looked around to me. His face didn’t change but he did compliment me and said I looked quite convincing. I walked over and sat in a chair next to his and lit a cigarette. I could see out of the corner my eye, him looking me up and down and then he said the funniest thing “do you shave your legs?” Lol. I finished my wine and stubbed out my cigarette and said some thing like “come on I want to see that cock of yours”. We walked back into the lounge and I stopped him and said, let’s start in here. We were stood in the centre of the lounge and to avoid eye contact, as much as possible, I manoeuvred myself so I was behind him. Sometimes it the most silly things that pop into your mind in these situations because I remember thinking “I hadn’t realised how tall he is, even in these heels, he’s taller than me.” He wasn’t wearing shoes so I helped him take his t-shirt off. Still stood behind him I put my hands on his belt buckle and asked him if he was ready. He didn’t say anything but just nodded. I undid his belt and his button fly and pushed down his jeans, he stooped to take them off. Once he was standing again I slowly moved my hands over his belly and down into escort karaman his boxer shorts. I touched his cock and he trembled violently. He said “I’m sorry, your the first person to do that” I was pleased to feel that he was starting to stiffen, I cupped his balls in one hand and very gently massaged them while stroking his shaft with the other. He was right, he was very long but surprisingly thin, which was very good news for me. I crouched down behind him and pulled down his boxers and he stepped out of them. I knelt down and massaged his cock and balls from behind. After a few minutes I said to him “for the next part I’m going to have to come around the front, I won’t be hurt if you want to close your eyes”. I shuffled around on my knees until I was facing him with his cock level with my face, I didn’t look up at him. His cock was pointing straight up and the head of it looked red and angry. I reached up and held the base of his shaft and gently pulled it down so his cock was pointing straight at me. I remember thinking back to the times with Steve when I was unable to show restraint and would just gobble him down. I didn’t want to scare Charles off and I wanted to prolong everything for as long as possible. So I just gently kissed the tip of it at first. I pulled away and licked his balls for a while, Charles himself just couldn’t stop making moaning noises. I licked my way slowly up his shaft and kissed the tip again. It was time so I opened my lips and let him in. He was far to long for me and I didn’t have the skill of deepthroating he started to chuckle when I got a bit too adventurous and he hit my gag reflex “try to take in too much did you?” I have to say it was wonderful being in that position again. Dressed, sexy underwear against my skin, kneeling down with a cock in my mouth. Wonderful!. I must have giving him that blow job for about 5 minutes when he said he wanted to go to the bedroom as he wasn’t sure how much longer he had before climax. That was actually something I hadn’t considered, I was well aware I was taking his virginity, but I hadn’t comprehended that as a consequence of it being his first time he would be too excited and not have much stamina. Dissapointing, but that’s only natural and not his fault. He followed me into the bedroom and he sat on the edge of the bed, his cock still pointing upright. I said “I’m keeping my bra, suspender belt, stockings and heels on for this” I lifted the dress up and over my head and stood in front of him in my lingerie. He was staring at my crotch so I wiggled about and took my time to pull my panties down, trying to tease him a little. When I finally pulled them down enough so he could see he just blurted out that I wasn’t joking when I said I had a small cock. I stopped pushing down my panties and used a couple of fingers to wave my cock at him and said, yeah, it is pretty small in comparison to yours. He moved to a kneeling position and said you still want to do this doggy? I said yes, I think it’s best if we have minimal eye contact. He slapped the bed in front of him and said come on then, I’m ready. I said “hold your horses tiger, you need to put a condom on and then we need to lube up”. I walked over to a bedside cabinet, my panties karaman escort bayan still half way down my thighs, amid took a condom out of the box and threw it over to him and said “stick this on”. I took a hand pump bottle of lube. I climbed out of my panties and turned towards the bed to find Charles struggling a bit with the condom, I asked him if he was ok and he said it was the first time he had put one on. I said, here, you hold this, passing him the bottle of lube and I will do that for you. As I was rolling it down his shaft he said it felt a bit uncomfortable but I told him we should really use one. Ok I said, shall I lube you and you lube me? Ok. I pumped some into my hand and started massaging his cock again, when it was good and slippery I said “my turn” and I flipped around and buried my face in the pillows and stuck my ass in the air. He asked what he needed to do and interned my head so I could speak to him while reached behind me to open my butt cheeks “pump some on t finger and then massage my hole with” he did that and it felt fantastic! “Right, now pump some more on and then use the finger to push the lube inside my ass, you need to gently finger fuck me to make the hole really slippery, it won’t affect you but it will make a massive difference to my enjoyment” I was in heaven, I had really missed being in this position “I think we are good to go he said”. Right, don’t come at me like a bull in a china shop, you need to firm but you are not looking to push all the way in, first time, we need to start gently and lead up to it, just push your cock against my anus, there will be resistance but it will give way to you, I don’t want anymore than the head in at first. He pushed and pushed and then he was inside me! Now you can start your strokes but just feed me a bit extra each time until we get you all in but if I stay stop, I really want you to because it means you will be hurting me. I relaxed as much as possible and he started, he was very gentle but doing ok and because he was so slim the pain for me wasnt to bad so I relaxed even more and was really enjoying myself. It took him a while to build up but eventually I was taking all 9 inches of him. I couldn’t believe it, I was being fucked again. It didn’t last long, just a few minutes really before he started bucking against me and moaning loudly as he came. I waited until I could feel him softening inside me and then raised my self up onto my elbows and slid off him. I moved over the bed slightly and just lay there and he joined me, lying on his back. I asked him if he was ok, he said he felt great and I just said to him that I had enjoyed it a lot and that is how you have sex. I reached out, without turning to face him and held his cock on my hand, the condom still there. Feeling around I thought I could feel what seemed to be a fair amount of cum in the end of it. I rolled around and lifted my head to look sure enough there was a big bag of cum there.”What are you looking at” he said. That’s a lot of cum in there, that is one cum shot I would like to have seen! Well we can go again if you like? Not now tiger, I need me after sex cigarette. I got off the bed and put my panties and dress back on. “You get dressed and join me on the balcony for a glass of wine and a smoke.”He joined me a few minutes later, he was smiling I felt a bit sorry for him so I said “if you want to go again, we can but let’s wait a couple of hours for you to get your strength back………”That will be in part 2.

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