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My first time

"A friend opens my mind to new possibilities"

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Author's Notes

"A totally unexpected experience but one I'd fully embrace over the fullness of time"

They say you always remember your first time, well for me there were a few 'firsts'! And this is one I'll never forget. After 40 odd years I now cherish these memories and that wonderful time of Discovery of my own sexuality 

Following on from when I accidentally inseminated my friend that night, I was desperate to meet up again, well the rest is history!  At that time I was friends with a man in his forties, Twice my age, a constant preference for me for the next 40 years! we both shared an interest in CB when it was popular, often chatting away until the early hours I soon got the offer of an eyeball , CB slang for a meet up. He wasn't far from me so I cycled over to the as I called it ' the posh side of town '  getting directions on my walkie-talkie. I arrived at his house, a nice three bed detached.  Although I was nervous I walked down the path, the door opened as I got there, here bring your bike in. Once in, he introduced himself as terry, we didn't use our real names on the CB , just what was known as  a Handle.

Terry was, I'd say, just under six foot with a slim physique , wearing just some tight nylon, slightly see through white shorts and a tee shirt . I was invited into what he called the parlour, a sumptuous room that looked like it had never been used. I sat down on a plush sofa whilst he made us a cup of tea. Coming back with two cups he sat down next to me. For the first time I noticed he wasn't wearing anything under his shorts, I could see the distinct outline of his cock. We chatted for a while about CB, and mundane stuff then out of the blue he asked if I had a girlfriend, I blushed as I recalled that night with my friend, sort of I replied, smiling at the memory of that night, lucky lady he replied, he showed me his new VCR, most of us could only afford to rent one but his was a top of the range with remote control, Wana watch a film? He asked, saying that he put on an obvious choice of film on the VCR, convoy! Throughout the film I noticed out of the corner of my eye that he kept looking at me, occasionally ' inadvertently ' placing his hand over the outline of his cock when he knew I was looking in his direction. I pretended not to notice but the small bulge in my trousers said otherwise.

Film over, he made us a coffee, have a look through the tapes and see if there's anything that you like. His videos were contained in two draws, the first one contained films I'd barely heard of, the second draw however was a real jaw dropper, just the titles suggested they were porn movies, had I accidentally come across these or did Terry know I'd see them? 

He came back in the room, Oh, you wasn't supposed to see them, an awkward silence ensued until I bravely said, well let's see what you got. I couldn't believe I'd just said that, a bit of bravado perhaps? but something deep within me was crying out for a bit of cock fun, I mean the signs were blatantly obvious, this evening was about to come more exciting than I could have ever imagined. A few predictable housewife films then I saw one called First time CD. Oh I innocently said, what's this one about? Knowing full well what it might be. He came straight out with it , don't you know? I played stupid and pretended not to know. Well let's put it on and see. With that he Inserted the cassette and the screen came up with some credits,he got up and switched the main light off ,the room only illuminated now  by a sole upright lamp in the corner of the room. In the dim light the movie started , a crossdresser on a bed with a couple of men. He'd somehow found my passion! I watched the screen  as the crossdresser succumbed to the men's advances, in a way wishing that it was me on that bed. My cock had now started to swell and show a distinctive outline, he saw this and just started rubbing his cock through his ridiculously tight shorts. As his cock grew, an outline of his swelling cock grew more pronounced  in his shorts and just kept growing to reveal a large cock Indeed maybe six inches but to me at that time that was big. Looking at me he asked, like what you see? I muttered something of approval and he grabbed my hand and placed it on his now rampant hard cock. This whole situation was totally unexpected. It got the better of me and I just froze. He sensed my nervousness and removed my hand resting on his cock. He apologised thinking he'd taken advantage of me, I replied no which was a relief for him then ,red faced, I explained that this was my first time touching another man's cock, I then told him what had happened with my  crossdressing friend and the missed opportunity I had to play with his cock after I'd accidentally inseminated him a while back, all the time he watched me then placed his hand on my leg. He came straight out with it , I knew you were a sissy, a moment's silence  then we both laughed, that truly broke the ice. So, what do you want to do? I gave it a quick thought and the prospect of finally sucking another man's cock at last and placed my hand back onto his cock, good girl he said and put the video back on. Instinctively my hand explored his shaft over his shorts. He liked that judging by the low moans he made, a few minutes later he turned to me and said , time to lose those,meaning my trousers, I was a bit hesitant as there would be a surprise he wasn't ready for. I got up and slowly dropped my trousers, he was very surprised as I was now standing in just my shirt and my girlfriend's pink panties with the tell tale damp patch of pre cum. Very nice he said as he patted the seat of his sofa for me to sit back down. Once down his hand immediately went to my panties , rubbing my cock back to full erection, I became more braver and started rubbing his now Rock hard cock, moments later he got up and removed his shorts his fat cock shot up to his waist, the head glistening with pre cum, that's better he said as he sat back down. My hand instinctively went back to it, this time gently moving my fingers up and down as I explored his thick veiny cock. The movie played on as the crossdresser in it was now being fucked by the two men. I wasn't sure what to do next but Terry soon guided me to the carpet and in-between his now wide open legs. I'd studied the movie and just tried to copy what I saw, this being my first time. Don't be shy Terry said, take your time, this was very reassuring as my heart was racing and a strange sensation coursing round my body.

I don't know why, either immaturity or curiosity, I smelt the tip of his cock and foreskin. The aroma of a freshly cleaned cock was a pleasing one and I just dipped my head onto his now purple swollen glans. My lips easily slipped over them, aided by the now large secretion of pre cum over the top of his hard fat cock.

 A sharp intake of breath from Terry confirmed I was doing it right, I didn't get the chance to do this with my friend that night so I was going to savour every minute of this. Now with my back to the screen, all I could hear was the sounds of the crossdresser being fucked, loud slapping sounds which I assumed was the guys balls slapping against his bottom as he was relentlessly fucked. Whatever it was certainly had the attention of Terry as he now held the back of my head to motion me into taking more of his thick cock into my mouth. Not as easy I'd thought it would be as he tried to force himself deeper into my virgin mouth. My sucking was replaced by his shallow thrusts into my now willing mouth. There was a very loud grunting from the film , I took it the man had finally cum into that crossdresser, at the same time Terry's thrusts became more forceful , I wasn't ready for this as a couple of thrusts saw his cock pushed into my throat, he held my head there, I tried to choke but couldn't, his cock now twitching as I experienced my first cock spewing warm jets of sperm down my throat, somehow I managed to swallow it, choking as he pulled out his now shrinking cock, sperm still leaking from it, clean it he demanded, without hesitation I did just that, getting every last drop. You'll make a good cum slut , how right he would be!.

It was getting late and the weather outside was dreadful as heavy rain hit the windows. 

Terry offered me a bed for the duration, I didn't know at the time he ment his but after what I'd just done, there'd be no surprises!

And Oh he said , I think we've some unfinished business as he slapped me still pantie encased bottom although now ruined by all my pre cum that now soaked them, my girlfriend would be asking questions if I couldn't clean them.

We made our way upstairs, I think we'd both better  take a shower before bed Terry said to me , ok no problem I thought, he bought two towels and led me to the shower room, the shower was huge! more than enough room for two.

He ran the shower and I went to take my girlfriends panties off, No, keep them on. I did as I was told the water soon made them translucent much to Terry's delight we ended sensually soaping  each other, my erect cock clearly visible through the thin material of my girlfriend's pink panties.

Terry now  paying particular attention to my cock, soaping my panties in an effort to make them more see through , my cock now painfully hard and needing urgent attention. 

Now paying particular attention to my bottom, he slipped his hands into my panties caressing and pulling my cheeks apart as he rubbed soap over them, he made me jump when he ran his hand over near my entrance and slipped a soapy finger into me. This I wasn't expecting but the naughtiness of it was now really making me horny. He did it again but with two fingers, they slipped in  causing some discomfort as he twisted them around in me. kissing my neck he said he'd be gentle with me 

Things now had gone beyond what I was expecting but I wanted more. Sensing I was ready he threw me a towel. Removing my wet panties I dried myself off. He'd gone to his bedroom, wait there he said, a couple of minutes later I was told to come in to him.

There he was, lying on the bed,  his cock now revived wearing nothing but a satin blue and black suspender belt and black stockings. I'd seen enough, my cock standing proudly to attention. I got onto the bed with him not sure what he had in mind,just a bit of cock fun I thought. It all started off with him running his hands all over me, paying particular attention to my nipples, this I was enjoying as my nipples stood to attention, he played with them,pulling at them so my nipples  became elongated before letting them go to snap back to my body, a few twists which were painful before one last tug on them. Right slut,I come first, got it? Well this wasn't just a hand job and a suck, I was about to experience something I'd not even contemplated would be happening  before this evening and something that would put me on the path of sissification forever.

His hand wondered teasingly over my cock, now desperate to cum. Pulling my foreskin back , his finger and thumb played with my now throbbing glan. He then did something unexpected but equally sensual that almost made me cum there and then, he softly gripped under my glan and with some of my pre cum and  moved them sideways , this had an immediate effect ,I was not able to hold back, what had Terry just done to me? 

He knew the signs and stopped leaving me totally frustrated as I'd ever been,desperate to release my pent up cum.

Ok, trust me he said, with that he rolled me onto my front and something cold was squirted into my crack, it slowly ran down my cheeks and onto my ball sac as he massaged it in, another sound of something being covered in lube, then he pulled me down the bed and up onto my knees, I knew what was going to happen as my heart now raced.

Terry asked if I'd done this before, well no I replied, good I'll break you in easy then. To be honest when he said that it did scare me as I never thought I'd be in this position but Terry was very reassuring which made me just that little bit relaxed but also excited.

He was gentle with me , sliding his cock up and down my crack, just as I'd done with my friend, every time his cock passed my sphincter he gave a little push, maybe to try his luck but my body wasn't ready to accept him. This went on for a while , each attempt unsuccessful then he applied more lube and started over, on his second pass his cock hit home and the head of his cock had now opened me up to accept the tip of his short but fat cock , he stayed quite still  but kept gently pushing into me , I felt him slip a little deeper into me but accompanied by some pain, Terry told me to relax, I did my best as he tried to force his cock into me, not easy to do as this was my first time, he kept the pressure up in an attempt to finally fully penetrate me, the pain subsided and I instinctively relaxed then it happened, in a final push he slid all the way in , may be  only six inches but it felt like I'd been taken my something far larger, a sharp pain accompanied his successful attempt to breed me. Terry tapped me in the shoulder, good girl, I knew you could take it. I was already being referred to as a woman and enjoying the compliment,  Again, the very early stages of my sissification and one I'd embrace fully over time.

The pain had now subsided, the weird feeling of being full and ready for Terry to continue ' breaking me in' as he called it, my current position of being impaled by another man was something that hadn't even crossed my mind  only hours earlier, yes, I'd thought about it often but I thought it would be me making love, not being made love to! My cock giving away how excited I was by the pre cum now hanging off my cock towards the bed sheets. All this time Terry had remained still, he sensed it was time for my deflowering and slowly pulled back, my sphincter instinctively tried to push him out but Terry was in control and pushed himself back fully into me, still some pain as I was still getting accustomed to accepting his fat cock now slowly stretching my tight hole. Slowly he started thrusting into me, the pain was now subsiding so I was able to enjoy this new experience. He was gentle and considerate the whole time. My whole experience only lasted less than five minutes but those five minutes I'll remember forever! 

He stared to breath quite deeply as his slow thrusts continued, then it happened and a fantasy fulfilled as he gripped my hips tightly and made a Loud grunt as I felt a strange sensation of his cock twitching inside me then a few quick forceful thrusts then a warm sensation as he came inside me. As he came in me,  his arms went around me in a a tight grip, now I could feel his cock spewing cum into me, Terry cried out  as he came , a final few more forceful thrusts as his climax, filling me with every last drop of sperm he could muster. As his swelling inside me subsided, he kissed the back of my neck as we collapsed on to the bed, Terry now spent , his cock now losing its firmness to it slowly slid out of my now sore passage. He wasn't finished with me yet, I had a hard in that was in desperate need of attention.

He spun me over, my rock hard cock pointing to the ceiling, he laid next to me , he was to savour every minute with me. Stroking my nipples, they erected to his touch as he brushed over the tips of my nipples, I nice but strange sensation went through me, my cock felt like it was tingling every time he did it, what Whatever he was doing I was enjoying it. He went in for a kiss, pushing his tongue into my mouth as his hand explored my body.  I'd never been kissed by a man before so responded , he liked that  , the excitement of the situation got the better of him as he gave me a love bite in my neck, something I'd find difficult to explain away, he then went for my nipples  sucking each in turn , I was in total ecstasy the link to my shop, nipples both super sensitive as he made his way to his prize, kissing my skin as he made his way there. He kissed the tip of my now throbbing cock then put his lips around the head, flicking his tongue around my glans, that was the trigger, oh no you don't as he pulled his head back. I was certain I was about to shoot my load but somehow he stopped it. Didn't know at the time but he called it edging me, well whatever it was I was loving the sensation, he came in again, this time I was ready but again I got to the point of no return, or so I thought, and he moved away. This was the most frustrating but enjoyable thing I'd ever experienced up to that point. Think I'd better finish you off he said, gently wrapping his finger and thumb over my swollen helmet. With slow movements he slid his finger over my now drenched in pre cum glans, he watched my face as I closed my eyes, the sensation of me about to cum was building up within me , open your eyes and watch , I did so  and then it happened, a sudden feeling of immense pleasure, I cried out, nooooooo, Terry liked that , then I had the most powerful orgasm I'd ever experienced, jets of my cum shooting upwards like a fountain, powerful spurts as I kept shooting skywards, a good four spurts shot up then back down onto my chest. I was out of breath, that's it I thought, time to clean up but Terry had other ideas, and clasped his lips around my now shrinking cock , sucking off any remaining sperm before rubbing the rest on my chest over my nipples, playing with it, pulling up the sperm from my nipples in long strings. This really was the most amazing thing I'd ever had done to me and now I wanted more!

Once he'd had his fun I was told to shower and if I wanted I could stay till morning as it was raining. Whilst in the shower I could hear him on his phone, who could it be calling at this early hour, a few hours later I'd certainly find out.

Terry had a king sized bed so said I could share if I wanted ,we could keep each other warm. I went in naked and Terry did the same, he spooned up to me l, his arms wrapped around me, I'll admit I was enjoying all loving attention. We talked for a while and asked how I felt about what had just happened, I told him it was something I'd thought about but never really got round to it, preferring to fuck my friend. He was interested in what I'd done with my friend and asked questions about what I was looking for. He got round to talking about the threesome we'd watched on the VCR and had I ever contemplated that myself ,well not really I said, really? He said he comforted me, I liked that as his arms wrapped around me again, his hard cock sticking into my cheeks. I guess I was more feminine than I'd admit but what had just happened felt natural for me and would open the gates to a lifetime of being a sissy slut.

Terry carried on with this line of questions until he was sure he could ask the question he wanted to ask me all along. ' so would you be interested in doing it? I'd forgotten I have a friend popping over later, I told him you was here and he is certainly interested in meeting you. 

Well , what do you say to that I thought, lying naked in bed with another naked man? 

Half a hour later there was a knock at the door, my heart was pounding as I was about to be the focus of two men , could I go through with it?

To be continued??

Written by Christine63

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