Hello all ISS readers. My name is Rajveer and I am 29 years old Bisexual bottoms guy from Bangalore. I am fair, with a height 5’7; average built and weigh about 80 Kg. I am a regular reader of ISS and been trying to post my story since a long time, but due to busy schedule I was not able to spare time to ink it. I am glad that finally I am writing my story which happened to me about 2 months back. I am on an adult dating site and one day I received a mail from a guy named Rajesh. He said he was interested in having sex with me. I mailed him back and we exchanged our details and spoke over the phone. He said he was experienced and I also wanted to try him out. A few days later we decided to meet up on a weekend night for a stay over at my place. I was quite excited and waiting of the weekend. Finally on Saturday afternoon I spoke to Rajesh and fixed up to meet at night at about 10:00 pm. After I spoke to him I had lunch and though of preparing myself for the night. Let me tell you that I like to cross dress as well if my partner wants me to, or is comfortable with it. I don’t dress like professional cross dressers but yet nicely and sensuously because I believe, all that matters is how sexily you carry yourself. I went inside my room and locked myself up. The idea was to shave myself. I then shaved my face, my chest, my armpits and then my pubes. I am not very hairy but shaving gives a wonderful feeling. It took me almost 2 hours to shave and have bath and rinse myself thoroughly. I then put a small removable butterfly tattoo on my arm just below my shoulder. The day passed and the night finally mushroomed. It was about 10:00 and there was no sign of Rajesh. He then messaged me saying he would come a little late as he had guests at home. I was waiting in anticipation just to receive a call from him saying he’s already left and will be home in 10 minutes. He reached my home at 11:30 and I greeted him. Let me describe Rajesh, he is 24 years with a height about 5’6 and medium built. He is a little tan and his cock is not too big but adequate to satisfy anyone. We went straight to my room and locked it up. It was quite cold outside. He removed his jacket and shoes and we both settled on my bed and started talking. We spoke to each other in person and were trying to know each other better. We spoke earlier as well so we knew each other’s preferences. After a heated up discussion we finally decided to break the ice. I went to the bathroom and undressed myself out of my shorts And T-shirt and slipped into a sexy green sleeveless cotton frill tank top and a beige net G-string. I applied some nice perfume and came out just to see Rajesh stunned with his eyes popped out and jaws fallen on the ground. I felt good and horny looking at his reaction and went to my bed after switching off the lights. My laptop was on and loaded with porn movies which we planned to watch while having sex. The screen brightness of the laptop was the only light in the room making the atmosphere more sensual. Rajesh followed me in the bed naked. I was so excited that I didn’t even realize when he removed his clothes and came over on the bed. His arms grabbed me from behind under my shaved armpits playing with my nipples over the top which I was wearing, as I was facing my back towards him switching on the porn video. I was feeling aroused and erect as his thriving cock was poking my back and his fingers were exploring and caressing my shaved body. He was squeezing and lightly pinching my nipples and slowly biting my earlobes. Then he held me tight with his one arm and put his other hand between my thighs caressing my ass cheeks and cock inside the G-string. I could see that he was not able to resist and was struggling to push my panties aside without removing them to shove his finger in my love hole. He was teasing my asshole and then finally succeeded in entering his finger just to find out the tight hole waiting for him. It gave me a divine pleasure wanting for more. He 1st fingered me slowly and then vigorously since he was also turned on. It was a lil painful but nice. While he did that I was melting and squirming in his arms. Moments later he came over me and lifted my legs and removed my G-strings and the girly tops and made me nude. He came on top of me and lifted my hands and started licking my shaved armpits and the area surrounding my nipples while his cock was poking my love hole. OMG I was in the ninth heaven. I never had this feeling before. I held him tight indicating how much I was enjoying and so did he by sucking and licking me hard. I held his cock in my palm while he was busy licking and sucking me but even before I could realize he got up and shoved his cock in my mouth. Oh it was a mouthful and I enjoyed every bit of it. I sucked it and lapped it up like a pro. After a while when we were in tune, he lifted my legs and placed them on his shoulders. He wore a condom and started teasing my love hole with his cock. He tried to push it in but could seldom enter. I helped him by lubricating myself and stretching my hole for him giving him the direction to enter me. He entered very slowly and nicely and it was less painful. He held me and fucked me slowly 1st and then after a few strokes his pace increased. I was just lying down with my eyes closed enjoying the fuck while I was moaning. After fucking me for a while in this position he removed his cock and asked me to turn positions. He made me a doggy then and asked me if I would like it without the condom. I was so turned on that I didn’t utter a word but just nodded my head and agreed as I couldn’t wait for more. We both were really enjoying and we were least bothered to watch the porn video which was going on in My laptop while we were fucking. He threw away the condom and this time my hole was adequately big for him to enter so he entered with a thrust. I scream in pain as I felt his MEATY COCK which gripped nicely to my hole. He held me by my waist and started fucking me quite fast and hard now and I was moaning continuously as this was the moment I was waiting for since the time we spoke over the phone. To be honest I was craving for it. Meanwhile I asked him not to cum inside me. He was ready to cum after a few hard jerks/strokes he gave me. He removed his cock and sprayed his hot, sticky thick cum all over my ass. He then scattered it with his cock which was wow. He rubbed me clean and went to the bathroom to clean himself while I was still lying naked in the bed. Rajesh came out and told me that I was really soft and sexy in bed and he loved fucking me. He didn’t expect it to be this hot. It felt like he was fucking a girl.” I really liked the way he expressed it. By now he was tired and he told me that he wanted to sleep since he had a very tiring day as well. I asked him if we could sleep naked to which he agreed and minutes later he dozed off to sleep. It was about 1:30 at night and I was wide awake naked inside my blanket watching porn. After a while I again started feeling horny and I wanted more but I knew that Rajesh was hell tired and was deep asleep. He would get up in the morning and might have a session again and leave but as of now there was no chance. Anyhow, I grabbed his small dead cock while he was sleeping and started stroking it and rubbing it on my asshole. Since I was facing my back towards him I was sticking my bum to him so that I could reach his small cock while touching his naked body to my bare back. A few minutes later I felt his cock swelling in my palm as he was asleep and I was enjoying it even more because his cock was hard now and I loved to rub it in my hole. He shocked me when he got up partially and grabbed me from behind which was completely unexpected. I didn’t even think about it in my wildest dream that there was a second fucking session coming up, looking at how tired Rajesh was. He completely proved me wrong. He was partly sleepy and grabbed me and was poking me with his cock on my bum. He got up with his eyes barely open and then ripped off the blanket off me and himself. He then held me by my waist and made me to sit on my fours making me feel like a slutty, whory, desperate bitch begging for a fuck. He rubbed my hole 1st possibly cause he wanted to find the entrance as he was still partly sleepy and then he entered slowly. He started to fuck me slowly for a few minutes and then took a break to go the bathroom. He peed and washed his dick and came back. He then lifted me and made me go doggy again and held me tight by my waist and started fucking me furiously. It was a very erotic feeling as I could feel his cock ramming my asshole deep and hard and his balls slapping my ass cheeks. He went on fucking me continuously deeper and harder while he made me lie down on my stomach penetrating from behind me. It was so cold outside that it could shiver you but inside the heat was on the peak. It was like a fire and ice feeling. Trust me folks he fucked me in such a way I just can’t describe. My ass was literary on fire and it was paining as well so much that I couldn’t take it anymore but I was so turned on and horny that I didn’t wanted him to stop as well. I buried my face in the pillow, held the blanket tight, bit my lips and let him to continue fucking me. By now it was a two way effect, since I was lying on my stomach my cock was rubbing against my bed and it was paining and craving to cum and on the other side I was getting fucked so my ass was burning and paining. It was going on at the back of my mind – If this guy continues to fuck me like this for some more time I am gonna burst out Cumming but I still so want him to continue much longer. My legs were shivering and I loved each and every moment of it. He must have fucked me like that for about 10-15 minutes. No sooner he took out his cock and turned me to suck it. I could hardly suck it for 30 seconds just then he parted my legs and to ice the cake he started fucking me in intervals. I mean he inserted his cock with a thrust and then removed it completely and then again inserted it with a thrust making my love hole sore. He did like that about 15-20 times. It was quite painful but I could not say no. He was again ready to spray his load on me. He finally came but not that much this time how he formerly did. OMG it was still wow and I could not have asked for more. We cleaned ourselves and wore our clothes and finally hit the sack. I switched off my laptop and we went off to sleep. It was almost 3:00 in the morning and Rajesh had told me that he would want to leave at 6, 6:30 in the morning for his house. Early that morning I woke up partly as I could see the daylight through my window. Rajesh also got up and grabbed me and started rubbing my asshole over my clothes indicating a final fucking session coming up before he leaves. But I was in pain cause of the way he fucked me last night. I slowly pushed his hands away but he then removed my shorts and my bare bum was exposed to him. He tried pulling me but I was trying to resist as I was no more in the position to take pain. It looked like he wanted to fuck me. I thought of giving it a try since his touch was making me horny all over again. I stick out my bum for him to enter me. As soon as he entered me I was in deep pain. I pushed him and asked him to stop as it was paining badly. He agreed and understood. He then hugged me and left for his house. It was about 7:15 when he left. We do speak sometimes but till now due to our busy schedules we haven’t been able to meet up again. You guys must be wondering that I never mentioned about me Cumming that night. Well after Rajesh left I went in my room locked myself up and wore that girly outfit again and masturbated while thinking about each and every moment we spent fucking last night and came really nicely with a complete satisfaction. It was quite a girly feeling I had that night and I loved it beyond limits. It felt so different. But remember that I am not a professional cross dresser and I am not too much into being a girl. I am a Bisexual Male and I do this just for pure fun and fantasy. So that’s all folks. I am all horny dripping with pre cum after finishing this story. If you liked my story, I would really appreciate if you could leave your comments. It would inspire me to write more in case if I have any more encounters. I don’t mind meeting guys who are looking for sex and pure fun but not LTR. In case you want to know more about me or you think I am apt for a steamy session with you and fit your likes and preferences, we can meat (Meet) up and do it. You can write to me at Thank you all for reading my story so patiently. I hope to see lot of comments. Later folks.
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