First time Sissy
- 2 years ago
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My First Time As A Sissy free porn video
As you seemed interested in my first full on gay experience, I thought I would describe it for you in more detail. After my split up with my girlfriend of 3 years I was quite upset and found myself going to the pub more frequently than before. One Friday lunchtime I got chatting to Andy who used to pop in occasionally either with his girlfriend Fiona or on his own & today he was single. I would have been just 21 & he was in his late 20’2.We chatted about this & that & eventually our conversation turned to bikes & he told me he was just stripping down a Royal Enfield Continental GT 250cc, I told him this was ever schoolboys dream bike when we were 14 or 15 so he invited me round to his place to see it. During our walk to his place he mentioned that he hadn’t seen me & Niccy around together for a few weeks so I told him the story of our break up. By the time we got to his place I was feeling pretty upset but Andy cheered me up when he showed me the real wreck of the Enfield, we stood side by side looking at it & all of a sudden I felt his hand stroking my back which I thought was pretty odd! Anyway his arm went around me & hugged me, I turned to look at him & the next thing he kissed me full on the lips. My initial reaction was anger but Andy said I looked like I needed cheering up so I just stood there & he kissed me again, this time French style.
Up to this point I had no notion of having sex with a man but the kiss seemed to go on forever & I returned it passionately. We stopped & he led me by the hand from the garage upstairs & into a large bedroom at the back of the house. We kissed again & I was hard as a rock & I could feel Andy’s cock bulging through his trousers. We both undressed, me a little shyly at first as was really both confused & excited at this occurrence. We lay on the bed kissing and feeling each other’s cocks, mine about 7” & his a bit bigger but same thickness & both uncut. He started to lick my cock & balls & got into the classic 69 where we both lapped & sucked each other off. Then the moment of near orgasm for me, I was on my back & he told me to pull my knees right back and then his tongue started licking around my bum hole before he finally had his tongue inside me. The feeling was one of pure pleasure and my cock was dripping with pre cum and he asked me if I enjoyed it, yes I said so he continued licking & probing my virgin hole for another 10 mins or so. By this time I had nearly shot my spunk on several occasions but managed to hold back. He then got back into 69 & we started sucking each other off before I shot my spunk into his mouth & he swallowed it all down. Once I had cum I felt really guilty & actually cried, however Andy was really gentle and we had a nice cuddle together.
I k** you not, it was a complete revelation to me what had just occurred. In a matter of minutes I was hard again when Andy, who hadn’t cum yet, asked if could fuck me. I asked if it would hurt a lot and he promised he would be gentle. I was on all fours on the bed, Andy had got some sort of jelly cream which he started to finger me with, it was a nice feeling & then two fingers & finally he rubbed his cock against my hole, pushing gently at first and telling me to relax and finally he was inside me, the initial pain was intense & I cried out so Andy stayed still with his cock still inside me. He started moving in & out very slowly & I soon began to really enjoy the feeling and started pushing back so his cock was fully in. He kept this gentle fucking up for a few mins then I could feel his cock get bigger inside me & with a loud groan we shot his spunk deep inside me. I could feel his cock pumping his spunk for ages before he finally pulled out and lay down beside me giving me a lovely deep sensual kiss. I started to caress his cock & in a few mins he was hard again so I sucked him, could taste his spunk which was bitter but not unpleasant. He asked if I wanted to fuck him but I said for the time being I wanted to be the girl so he fucked me on my back with my legs over his shoulders and we kissed at the same time. Didn’t need any jelly cream this time as my hole was wet from his first spunk up. He must have fucked me like this for 10 mins before he shot his load inside me again, this time he left his cock in & we just kissed.
He got up & asked if I would like a drink so we had a brief intermission, drinking, laughing & smiling at each other. At that moment in time I would have walked off the end of the world for him as felt a deep contentment which I hadn’t had for the past few months. I suddenly thought to ask him where was Fiona & it turned out she was away overnight visiting her family so was safely out of town. Andy suddenly asked me if I had ever worn a girls panties, no I said but I once tried on a pair of my mums tights & got quite aroused so he opened some drawers & laid out a selection of panties & bras, tights, stockings & suspenders as well as a couple of vibrators. The vibrators he said belonged to Fiona but she sometimes fucked him with them when she was in the mood. Andy told me to put on some black panties, a black bra (Fiona has small pert tits) & then I put on stockings & he attached them to a suspender belt. There he said when he was finished, you are mine now , you are my very own sissy boy so we will have some more fun. He fucked me three more times that afternoon & although my boy pussy as I had now began to regard my bum hole was a little sore & still dribbling his spunk out down my leg, I felt totally contended.
We met at his place every Friday afternoon and at the weekend when Fiona was out of town. After about a month he asked me if I was happy with our sexual arrangement and I said most definitely. He said he was glad but wanted to ask me something but was afraid how I would react so I said that as far as I was concerned he could ask me anything at all. He wanted another person to join us, Fiona I asked tentatively as I really fancied her despite getting my hole filled with her boyfriend’s cream! Yes he replied smiling, I asked how that had arisen & he explained to me that Fiona was aware of his bi side and had said on more than one occasion when we had met in the pub that I was sweet and she would be up for a threesome.
So the next Friday afternoon I called as usual & it was Fiona who answered the door with a cheery hello, I could feel myself blushing but Fiona put her arm around me and we walked into the lounge where Andy was sat reading a book. We chatted for a short while and then Andy suggested that I go upstairs with Fiona and make myself his pretty little girlyboy, Fiona he added was going to put make up on me! I followed Fiona eagerly upstairs and we went into the back bedroom where she immediately pulled off her T shirt revealing a pair of small but pert tits with large & prominent nipples. I must have been staring so she told me to undress which I did & soon I was stark naked with a huge hard on. By this time Fiona was also naked, her cunt was lovely and smooth with no pubic hair at all. She looked at me and said she liked what she saw & could understand why Andy was so keen to get me into bed. She gently pulled back my foreskin & my cock was already oozing pre cum which she licked off her fingers and told me to sit on the bed which I willingly did. She started off by applying makeup, then eye shadow and finally painted both my finger & toe nails in a vivid crimson before applying the same shade lipstick. Then she selected matching black lace bra & panties & black suspender belt with black stockings & helped me to put them on. Finally she got a long black haired wig & put that on me, there she said, you are now our little girl to do with what we like!
Only then was I allowed to look into the mirror-----the stranger staring back at me really looked sweet & feminine & I had to pinch myself to remind me it was actually me & not a girl, that is how realistic Fiona had made me over. I turned to Fiona and hugged her & we kissed, our tongues probing each other’s mouths. I felt her cunt, she parted her legs & my fingers wet into her wet slit, I rubbed her clit and she gasped out with pleasure but pulled away and said we ought to wait for Andy. She called downstairs and said that their little girl was ready & waiting for him. Quick as a flash Andy appeared and looked at the two of us, Fiona naked and me wearing lingerie and even though I do say it myself looking pretty hot!
Andy whistled & said that I looked simply stunning & quickly added that Fiona did too. He told me to walk around the room so I did in my best girly style, hips swinging slightly and my lips slightly pouted. He told me to bend over & slapped me on my bum & told Fiona to give me a spanking as he was sure I deserved one. Fiona started spanking me, lightly at first but getting firmer before she stopped and came back with a leather belt & started to use that on me. She paused & suggested to Andy that maybe it would be a good idea if little Nicky as she called me was restrained whilst she administered my punishment & Andy thought it was an excellent idea! This was unexpected as Andy had never expressed any interest in bondage but I was happy in my role as sissy boy so gladly complied. I was spread-eagled on the bed face down with my wrists & ankles tied to the corners of the bed. Fiona spanked & lashed me with the belt quite hard & I cried out but was told to be quiet so I lay there whist the punishment continued. It hurt a bit but I soon also got a lovely warm feeling coming over me, my cock by this time was straining at the leash. At last it stopped and I felt my cheeks being parted and a dildo being slid into my arse which felt nice. Fiona asked me if I liked that & I said yes so she fucked me with it for a few moments before stopping & letting me out of my restraints.
I was then told to lie on the bed, Andy pulled my panties down and both he & Fiona took turns in licking my cock like an ice cream. Fiona said I was not allowed to cum until she gave me permission so I nodded meekly, really enjoying my new role as a totally submissive sissy boy to both Fiona & Andy. He pulled me to the edge of the bed & slid his cock into my boy pussy, I tensed as usual at first but soon relaxed and he started to fuck me harder & harder until with a groan he shot his hot spunk deep inside me.
Fiona then got on top of me in the classic 69 and started to very gently lick my cock whilst pulling my cheeks apart & fingering my hole, I was gasping & really near to shooting my load but Fiona seemed to sense when to ease off. I have never known my cock to be so hard! Meanwhile I was licking greedily at Fiona’s pussy and her bum hole, fingering both & sticking my tongue deep inside and licking her very prominent clitoris. I could feel her tense and shudder and she had the first of several orgasms that afternoon. She remained in situ and started to lick my rigid & wet cock, taking it deep into her mouth and fingering me at the same time.
Andy by this time, who had been sitting on a chair watching me & Fiona play, was rock hard again. He once again pulled me to the edge of the bed before sliding his cock into my spunk filled hole and started to fuck me in long slow strokes. Fiona was again squatting over my face & had hold of my ankles so that Andy could put his full 8” into my boy pussy whilst I was licking away at both of Fiona’s holes. I could suddenly feel Andy stiffen & suddenly he came again inside me, I could feel his cock twitching as his spunk was shot inside me. He pulled out & Fiona rolled off me, Andy then got me on all fours and started to lick my bum hole whilst slurping at his spunk which was slowly dribbling out of me.
He stopped and Fiona asked if I would like to fuck her, oh yes please I replied. Well do you want to fuck my cunt or my arse she asked teasingly, both I replied without any hesitation. She looked at Andy and said that seeing as I had been a good girlyboy she would let me. She got into doggy position and I gently put my cock deep inside her wet and hot cunt and pumped a few times before pulling out and started to push it into her bum hole. It was obvious that the she was used to being fucked up the arse as my cock slid in with hardly any force, mind you she was wet through with all her cunt juices running down into her crack. I managed to fuck her for only about 30 seconds before I could feel myself cumming & nothing I could do would stop it this time so I plunged my cock right in & felt myself cum like a pressure hose! My spunk seemed to keep spurting up her arse for ages and with a groan I pulled out and collapsed on the bed. I lay there in a crumpled heap for a few seconds as Fiona got off the bed & went to a bedside cabinet from which she removed a strap on cock, I had never seen one before and was fascinated as Fiona put it on & told Andy to lay on the bed in doggy position which he did, Fiona lubed the strap on and thrust it deep into Andy’s bum hole making him grunt with pain, she fucked him really hard taking long strokes & burying the strap on right up to the hilt. Whilst this was going on I slid under Andy and started to suck his rapidly hardening cock and soon he was fucking my mouth in timing with Fiona’s thrusts.
Up to this point I had no notion of having sex with a man but the kiss seemed to go on forever & I returned it passionately. We stopped & he led me by the hand from the garage upstairs & into a large bedroom at the back of the house. We kissed again & I was hard as a rock & I could feel Andy’s cock bulging through his trousers. We both undressed, me a little shyly at first as was really both confused & excited at this occurrence. We lay on the bed kissing and feeling each other’s cocks, mine about 7” & his a bit bigger but same thickness & both uncut. He started to lick my cock & balls & got into the classic 69 where we both lapped & sucked each other off. Then the moment of near orgasm for me, I was on my back & he told me to pull my knees right back and then his tongue started licking around my bum hole before he finally had his tongue inside me. The feeling was one of pure pleasure and my cock was dripping with pre cum and he asked me if I enjoyed it, yes I said so he continued licking & probing my virgin hole for another 10 mins or so. By this time I had nearly shot my spunk on several occasions but managed to hold back. He then got back into 69 & we started sucking each other off before I shot my spunk into his mouth & he swallowed it all down. Once I had cum I felt really guilty & actually cried, however Andy was really gentle and we had a nice cuddle together.
I k** you not, it was a complete revelation to me what had just occurred. In a matter of minutes I was hard again when Andy, who hadn’t cum yet, asked if could fuck me. I asked if it would hurt a lot and he promised he would be gentle. I was on all fours on the bed, Andy had got some sort of jelly cream which he started to finger me with, it was a nice feeling & then two fingers & finally he rubbed his cock against my hole, pushing gently at first and telling me to relax and finally he was inside me, the initial pain was intense & I cried out so Andy stayed still with his cock still inside me. He started moving in & out very slowly & I soon began to really enjoy the feeling and started pushing back so his cock was fully in. He kept this gentle fucking up for a few mins then I could feel his cock get bigger inside me & with a loud groan we shot his spunk deep inside me. I could feel his cock pumping his spunk for ages before he finally pulled out and lay down beside me giving me a lovely deep sensual kiss. I started to caress his cock & in a few mins he was hard again so I sucked him, could taste his spunk which was bitter but not unpleasant. He asked if I wanted to fuck him but I said for the time being I wanted to be the girl so he fucked me on my back with my legs over his shoulders and we kissed at the same time. Didn’t need any jelly cream this time as my hole was wet from his first spunk up. He must have fucked me like this for 10 mins before he shot his load inside me again, this time he left his cock in & we just kissed.
He got up & asked if I would like a drink so we had a brief intermission, drinking, laughing & smiling at each other. At that moment in time I would have walked off the end of the world for him as felt a deep contentment which I hadn’t had for the past few months. I suddenly thought to ask him where was Fiona & it turned out she was away overnight visiting her family so was safely out of town. Andy suddenly asked me if I had ever worn a girls panties, no I said but I once tried on a pair of my mums tights & got quite aroused so he opened some drawers & laid out a selection of panties & bras, tights, stockings & suspenders as well as a couple of vibrators. The vibrators he said belonged to Fiona but she sometimes fucked him with them when she was in the mood. Andy told me to put on some black panties, a black bra (Fiona has small pert tits) & then I put on stockings & he attached them to a suspender belt. There he said when he was finished, you are mine now , you are my very own sissy boy so we will have some more fun. He fucked me three more times that afternoon & although my boy pussy as I had now began to regard my bum hole was a little sore & still dribbling his spunk out down my leg, I felt totally contended.
We met at his place every Friday afternoon and at the weekend when Fiona was out of town. After about a month he asked me if I was happy with our sexual arrangement and I said most definitely. He said he was glad but wanted to ask me something but was afraid how I would react so I said that as far as I was concerned he could ask me anything at all. He wanted another person to join us, Fiona I asked tentatively as I really fancied her despite getting my hole filled with her boyfriend’s cream! Yes he replied smiling, I asked how that had arisen & he explained to me that Fiona was aware of his bi side and had said on more than one occasion when we had met in the pub that I was sweet and she would be up for a threesome.
So the next Friday afternoon I called as usual & it was Fiona who answered the door with a cheery hello, I could feel myself blushing but Fiona put her arm around me and we walked into the lounge where Andy was sat reading a book. We chatted for a short while and then Andy suggested that I go upstairs with Fiona and make myself his pretty little girlyboy, Fiona he added was going to put make up on me! I followed Fiona eagerly upstairs and we went into the back bedroom where she immediately pulled off her T shirt revealing a pair of small but pert tits with large & prominent nipples. I must have been staring so she told me to undress which I did & soon I was stark naked with a huge hard on. By this time Fiona was also naked, her cunt was lovely and smooth with no pubic hair at all. She looked at me and said she liked what she saw & could understand why Andy was so keen to get me into bed. She gently pulled back my foreskin & my cock was already oozing pre cum which she licked off her fingers and told me to sit on the bed which I willingly did. She started off by applying makeup, then eye shadow and finally painted both my finger & toe nails in a vivid crimson before applying the same shade lipstick. Then she selected matching black lace bra & panties & black suspender belt with black stockings & helped me to put them on. Finally she got a long black haired wig & put that on me, there she said, you are now our little girl to do with what we like!
Only then was I allowed to look into the mirror-----the stranger staring back at me really looked sweet & feminine & I had to pinch myself to remind me it was actually me & not a girl, that is how realistic Fiona had made me over. I turned to Fiona and hugged her & we kissed, our tongues probing each other’s mouths. I felt her cunt, she parted her legs & my fingers wet into her wet slit, I rubbed her clit and she gasped out with pleasure but pulled away and said we ought to wait for Andy. She called downstairs and said that their little girl was ready & waiting for him. Quick as a flash Andy appeared and looked at the two of us, Fiona naked and me wearing lingerie and even though I do say it myself looking pretty hot!
Andy whistled & said that I looked simply stunning & quickly added that Fiona did too. He told me to walk around the room so I did in my best girly style, hips swinging slightly and my lips slightly pouted. He told me to bend over & slapped me on my bum & told Fiona to give me a spanking as he was sure I deserved one. Fiona started spanking me, lightly at first but getting firmer before she stopped and came back with a leather belt & started to use that on me. She paused & suggested to Andy that maybe it would be a good idea if little Nicky as she called me was restrained whilst she administered my punishment & Andy thought it was an excellent idea! This was unexpected as Andy had never expressed any interest in bondage but I was happy in my role as sissy boy so gladly complied. I was spread-eagled on the bed face down with my wrists & ankles tied to the corners of the bed. Fiona spanked & lashed me with the belt quite hard & I cried out but was told to be quiet so I lay there whist the punishment continued. It hurt a bit but I soon also got a lovely warm feeling coming over me, my cock by this time was straining at the leash. At last it stopped and I felt my cheeks being parted and a dildo being slid into my arse which felt nice. Fiona asked me if I liked that & I said yes so she fucked me with it for a few moments before stopping & letting me out of my restraints.
I was then told to lie on the bed, Andy pulled my panties down and both he & Fiona took turns in licking my cock like an ice cream. Fiona said I was not allowed to cum until she gave me permission so I nodded meekly, really enjoying my new role as a totally submissive sissy boy to both Fiona & Andy. He pulled me to the edge of the bed & slid his cock into my boy pussy, I tensed as usual at first but soon relaxed and he started to fuck me harder & harder until with a groan he shot his hot spunk deep inside me.
Fiona then got on top of me in the classic 69 and started to very gently lick my cock whilst pulling my cheeks apart & fingering my hole, I was gasping & really near to shooting my load but Fiona seemed to sense when to ease off. I have never known my cock to be so hard! Meanwhile I was licking greedily at Fiona’s pussy and her bum hole, fingering both & sticking my tongue deep inside and licking her very prominent clitoris. I could feel her tense and shudder and she had the first of several orgasms that afternoon. She remained in situ and started to lick my rigid & wet cock, taking it deep into her mouth and fingering me at the same time.
Andy by this time, who had been sitting on a chair watching me & Fiona play, was rock hard again. He once again pulled me to the edge of the bed before sliding his cock into my spunk filled hole and started to fuck me in long slow strokes. Fiona was again squatting over my face & had hold of my ankles so that Andy could put his full 8” into my boy pussy whilst I was licking away at both of Fiona’s holes. I could suddenly feel Andy stiffen & suddenly he came again inside me, I could feel his cock twitching as his spunk was shot inside me. He pulled out & Fiona rolled off me, Andy then got me on all fours and started to lick my bum hole whilst slurping at his spunk which was slowly dribbling out of me.
He stopped and Fiona asked if I would like to fuck her, oh yes please I replied. Well do you want to fuck my cunt or my arse she asked teasingly, both I replied without any hesitation. She looked at Andy and said that seeing as I had been a good girlyboy she would let me. She got into doggy position and I gently put my cock deep inside her wet and hot cunt and pumped a few times before pulling out and started to push it into her bum hole. It was obvious that the she was used to being fucked up the arse as my cock slid in with hardly any force, mind you she was wet through with all her cunt juices running down into her crack. I managed to fuck her for only about 30 seconds before I could feel myself cumming & nothing I could do would stop it this time so I plunged my cock right in & felt myself cum like a pressure hose! My spunk seemed to keep spurting up her arse for ages and with a groan I pulled out and collapsed on the bed. I lay there in a crumpled heap for a few seconds as Fiona got off the bed & went to a bedside cabinet from which she removed a strap on cock, I had never seen one before and was fascinated as Fiona put it on & told Andy to lay on the bed in doggy position which he did, Fiona lubed the strap on and thrust it deep into Andy’s bum hole making him grunt with pain, she fucked him really hard taking long strokes & burying the strap on right up to the hilt. Whilst this was going on I slid under Andy and started to suck his rapidly hardening cock and soon he was fucking my mouth in timing with Fiona’s thrusts.
Leela
- 21.10.2020
- 7
- 0
