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During my time in the Navy we were often in Gibraltar for weeks at a time, myself and my friends would often piss up in a little out of the way bar that we knew as “Charles’s Bar" (can't recall the real name). Charles was a big, cheerfull and clearly very gay man, i took an immediate liking to him and to cut a long story short, i found myself helping behind the bar when he was busy.
This was to lead to my love of lingerie and introduced me to my sissy side. One evening i had stayed later than normal due to it being busy and by the time the bar had shut my friends were back on board, Charles said he was going to treat me to a drink and food at local nightclub for the work i had done.
The nightclub was a dark dingy place with a lot of male customers, we stood drinking at the bar and Charles was very tactile, constantly dr****g his arm around me and letting it slide down my back, his hand brushing my bottom. A friend of his came over a stood with us, one either side of me, we were pushed together because of the space and Charles angled his body so he could talk with his friend.
As we stood chatting I began to notice that Charles cock had begun to get hard as he pressed against me, his friend was also brushing up against me and every now and then they would have a conversation in spanish, both glancing at me as they spoke. I got the impression that I was Charles new sailor boy, which i found quite exciting. Before I knew it the club was closing and when Charles suggested we go back to his bar for a drink i was more than happy to say As we stood chatting I began to notice that Charles cock had begun to get hard as he pressed against me, his friend was also brushing up against me and every now and then they would have a conversation in spanish, both glancing at me as they spoke. I got the impression that I was Charles new sailor boy, which i found quite exciting. Before I knew it the club was closing and when Charles suggested we go back to his bar for a drink i was more than happy to say yes.
We sat at the at the bar together his hand resting on my knee, as we talked about girlfriends and things, he asked about how i satisfied my urges when I was away and was clearly excited as we talked about how I would toss myself off in various places around the ship, I even let slip that one occasion I had wanked off while thrusting a large carrot up my arse.
I was getting more excited my self and when he asked if he could kiss me I did not object, we pressed a against each other as we french kissed, he held me close with one hand and slid the other between us and began to rub my cock through my jeans. We kissed and caressed for several minutes, then completely out of the blue he asked i liked wearing women's underwear, I said I hadn't tried it before but was excited by the thought of it.
He opened a cupboard behind the bar and said try anything you like, it was a true alladins cave of sexy lingerie, there was everything a sissy could desire. I chose a pair of white stockings and suspender belt, a pink bra and a pair of low heels, I finished it off with white girls shirt, unfortunately none of the skirts fitted me. My cock was absolutely rock hard now, I new then that I had found my secret desire. I came around the bar and Charles had got me a drink, you look so sexy he said and reached for my cock which the panties were struggling to hold. He pulled me toward him and we kissed again, this time he was carressing my arse and slowly wanking my cock, I reached down and undid his trousers and let them fall to the floor, i carressed his cock through his pants and felt him harden, i unhitched his pants and pushed them down grasping his cock as it came free.
At this point he suggested we move over to the mat he had obviously got out while I was putting on the lingerie (clearly he knew he was onto a winner). We lay down facing each other, kissing and fondling each others cocks. While I was very excited, i was also very inexperienced and had not yet learned the joys of cock sucking and was not going to allow him to put his cock up me. So we kissed for a few minutes and obviously sensing my nervousnes my asked what I would like to do. Whatever you like i mumbled, at this point he broke away from kissing me and moved down to my legs, he parted my legs and got between them, he was rubbing his hand up an down the stocking telling me what a lovely cock i had and that he would love to feel it inside him. I looked down at him knelt between my stocking clad legs, my skirt pushed up around my waist, with the suspender straps taut against my thighs and and had never felt more sexy than this. Slowly he lowered his head towards my rock hard cock, as he reached it he began to lick and kiss the head, before slowly parting his lips and taking the head in his mouth.
He sucked and licked my cock, taking it deep into his mouth then withdrawing and licking up and down the shaft. He started to lick and suck my balls and i could feel his tongue probing towards my hole, this carried on for several minutes with him alternating between my cock and balls. I knew i couldn't last much longer, sadly I have always been a quick cummer, I told him that I was near to cumming. Still gently wanking my cock he raised himself to a squat and positioned himself over me, he lowered himself a little and started to rub my cockhead around his hole, he had i noticed already lubed his hole ready for action. At this point he looked at me and said “I want to feel your lovely cock Inside me, I want to feel your cum trickle out of my hole".
So here i was laying on my back in stockings, suspenders, and panties, my cock stood up like a flagpole being slowly wanked by a guy who was intent on lowering himself and taking me deep in his asshole. This unfortunately for me was where nerves and inexperience took hold and i flatly refused, he stayed there for a little while longer gently caressing the area around his hole with my cockhead. He asked me several more times and i refused each time, fortunately for me he had not lost his enthusiasm for my cock and knelt back between my legs and started to lick and suck my cock again.
This went on for several more minutes and could feel myself building up to climax, “I am going to cum" i said to him and he acknowledged this by sucking me more deeply and grasping my balls. Clearly he knew when I was about to cum and as i felt myself climax, I pushed my body up trying to get deeper into his mouth. For a split second he clamped his mouth over my cock and squeezed my balls, i could feel my cum spurting into his mouth. He had other ideas though and before I had finished cumming he raised his head and I shot my cum over his face. He looked at me, cum running down his chin and thanked me for a lovely load. He then proceeded to lick and suck all of the cum from my cock and wiped the cum from his face onto his fingers and eagerly lapped it all up.
He lay back down next to me and we kissed and cuddled for a few more minutes, i had been slightly worried about him pushing my cum back into my mouth when he kissed me, but he had already swallowed it all. It was at this point that i realised that he had not cum, and to be honest he was already going soft. I asked if he would like me to wank him off, he thanked me but declined saying that he was happy just to have pleased me.
And that was that, sadly I did not have another opportunity to spend time with him during that visit and due to my leaving the ship not long after, I did not return to Gib for several years, by which time he had moved on.
During my time in the Navy we were often in Gibraltar for weeks at a time, myself and my friends would often piss up in a little out of the way bar that we knew as “Charles’s Bar" (can't recall the real name). Charles was a big, cheerfull and clearly very gay man, i took an immediate liking to him and to cut a long story short, i found myself helping behind the bar when he was busy.
This was to lead to my love of lingerie and introduced me to my sissy side. One evening i had stayed later than normal due to it being busy and by the time the bar had shut my friends were back on board, Charles said he was going to treat me to a drink and food at local nightclub for the work i had done.
The nightclub was a dark dingy place with a lot of male customers, we stood drinking at the bar and Charles was very tactile, constantly dr****g his arm around me and letting it slide down my back, his hand brushing my bottom. A friend of his came over a stood with us, one either side of me, we were pushed together because of the space and Charles angled his body so he could talk with his friend.
As we stood chatting I began to notice that Charles cock had begun to get hard as he pressed against me, his friend was also brushing up against me and every now and then they would have a conversation in spanish, both glancing at me as they spoke. I got the impression that I was Charles new sailor boy, which i found quite exciting. Before I knew it the club was closing and when Charles suggested we go back to his bar for a drink i was more than happy to say As we stood chatting I began to notice that Charles cock had begun to get hard as he pressed against me, his friend was also brushing up against me and every now and then they would have a conversation in spanish, both glancing at me as they spoke. I got the impression that I was Charles new sailor boy, which i found quite exciting. Before I knew it the club was closing and when Charles suggested we go back to his bar for a drink i was more than happy to say yes.
We sat at the at the bar together his hand resting on my knee, as we talked about girlfriends and things, he asked about how i satisfied my urges when I was away and was clearly excited as we talked about how I would toss myself off in various places around the ship, I even let slip that one occasion I had wanked off while thrusting a large carrot up my arse.
I was getting more excited my self and when he asked if he could kiss me I did not object, we pressed a against each other as we french kissed, he held me close with one hand and slid the other between us and began to rub my cock through my jeans. We kissed and caressed for several minutes, then completely out of the blue he asked i liked wearing women's underwear, I said I hadn't tried it before but was excited by the thought of it.
He opened a cupboard behind the bar and said try anything you like, it was a true alladins cave of sexy lingerie, there was everything a sissy could desire. I chose a pair of white stockings and suspender belt, a pink bra and a pair of low heels, I finished it off with white girls shirt, unfortunately none of the skirts fitted me. My cock was absolutely rock hard now, I new then that I had found my secret desire. I came around the bar and Charles had got me a drink, you look so sexy he said and reached for my cock which the panties were struggling to hold. He pulled me toward him and we kissed again, this time he was carressing my arse and slowly wanking my cock, I reached down and undid his trousers and let them fall to the floor, i carressed his cock through his pants and felt him harden, i unhitched his pants and pushed them down grasping his cock as it came free.
At this point he suggested we move over to the mat he had obviously got out while I was putting on the lingerie (clearly he knew he was onto a winner). We lay down facing each other, kissing and fondling each others cocks. While I was very excited, i was also very inexperienced and had not yet learned the joys of cock sucking and was not going to allow him to put his cock up me. So we kissed for a few minutes and obviously sensing my nervousnes my asked what I would like to do. Whatever you like i mumbled, at this point he broke away from kissing me and moved down to my legs, he parted my legs and got between them, he was rubbing his hand up an down the stocking telling me what a lovely cock i had and that he would love to feel it inside him. I looked down at him knelt between my stocking clad legs, my skirt pushed up around my waist, with the suspender straps taut against my thighs and and had never felt more sexy than this. Slowly he lowered his head towards my rock hard cock, as he reached it he began to lick and kiss the head, before slowly parting his lips and taking the head in his mouth.
He sucked and licked my cock, taking it deep into his mouth then withdrawing and licking up and down the shaft. He started to lick and suck my balls and i could feel his tongue probing towards my hole, this carried on for several minutes with him alternating between my cock and balls. I knew i couldn't last much longer, sadly I have always been a quick cummer, I told him that I was near to cumming. Still gently wanking my cock he raised himself to a squat and positioned himself over me, he lowered himself a little and started to rub my cockhead around his hole, he had i noticed already lubed his hole ready for action. At this point he looked at me and said “I want to feel your lovely cock Inside me, I want to feel your cum trickle out of my hole".
So here i was laying on my back in stockings, suspenders, and panties, my cock stood up like a flagpole being slowly wanked by a guy who was intent on lowering himself and taking me deep in his asshole. This unfortunately for me was where nerves and inexperience took hold and i flatly refused, he stayed there for a little while longer gently caressing the area around his hole with my cockhead. He asked me several more times and i refused each time, fortunately for me he had not lost his enthusiasm for my cock and knelt back between my legs and started to lick and suck my cock again.
This went on for several more minutes and could feel myself building up to climax, “I am going to cum" i said to him and he acknowledged this by sucking me more deeply and grasping my balls. Clearly he knew when I was about to cum and as i felt myself climax, I pushed my body up trying to get deeper into his mouth. For a split second he clamped his mouth over my cock and squeezed my balls, i could feel my cum spurting into his mouth. He had other ideas though and before I had finished cumming he raised his head and I shot my cum over his face. He looked at me, cum running down his chin and thanked me for a lovely load. He then proceeded to lick and suck all of the cum from my cock and wiped the cum from his face onto his fingers and eagerly lapped it all up.
He lay back down next to me and we kissed and cuddled for a few more minutes, i had been slightly worried about him pushing my cum back into my mouth when he kissed me, but he had already swallowed it all. It was at this point that i realised that he had not cum, and to be honest he was already going soft. I asked if he would like me to wank him off, he thanked me but declined saying that he was happy just to have pleased me.
And that was that, sadly I did not have another opportunity to spend time with him during that visit and due to my leaving the ship not long after, I did not return to Gib for several years, by which time he had moved on.
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