After that memorable night with my friend I tried to process it, I wasn't gay? I did have a girlfriend. I didn't fancy men but a man dressed in sexy slips and nighties and dresses, well they definitely caught my eye and I did enjoy that unexpected night with my friend, a friendship that we built on over a couple of years until he got a job in London. So over several weeks I thought alot about that night which at first I felt a bit awkward when I bumped into my friend, he sensed this and after a couple of days called me to meet him in a cafe so we could talk, the best thing I ever did as once we met and the coffee flowed, he explained he wasn't gay, but enjoyed my company and attention he got. He then asked, and here's another moment I will never forget, look did you enjoy that night yes or no, I answered in a stutter yes. Then he asked if I enjoyed sex with my girlfriend, again Yes. Well then he said, you're what's known as a bisexual with the added bonus of enjoying wearing lingerie so,like me you can relax and enjoy yourself, I'm not judging you, let's face it I bet you were a little apprehensive that night. For the first time I answered fully relaxed now and said no I was hoping you'd confirm what I already knew and just to add Yes I dress as well and so glad we did what we did. Well we'll have to do something about that, do you have a female name? Well I'd never thought of that but as you can guess by my profile name, he gave me one which I still use to this day.
Ok then, looks like we need a night in and try some of my things on and see what suits you. A date was made for our next encounter and my first introduction into O&A another first and another night to remember forever.
The next few days I had serious butterflies in my stomach for sure questioning myself should I go through with this, well I'm pleased to say the excitement of what may happen won the day so I was all set to meet my friend for a night I'd remember for a very long time.
The day arrived and to be honest, it felt more like a date with the excitement and nerves.
I arrived at his flat just before 8, a slight hesitation before knocking on the door, a quick knock and the door opened to reveal this beautiful blonde long haired woman with immaculate makeup and red lipstick in a summer dress hanging just below her knees with black tights? I'd find out later they were something a bit more exciting! and high heels.
Come on in she said in a recognizable voice and make yourself comfortable, I tried hard to imagine this was my friend but all I could see was this sexy young lady.
We drank tea and talked all things girly then she said, ok let's see if we can find something suitable for you, her wardrobe was extensive and we looked through some very nice outfits then she came to a pink item, ahh this is definitely you and pulled it out to reveal a maids outfit with matching panties. Ok you get changed whilst I find some suitable leg wear. I went to the bathroom and put on the outfit, looked in the mirror thinking wow, not bad at all. I came out where my friend was waiting, here he said, let me put these on you, it was a suspender belt and sheer stockings. Once fitted he gave me an approving look and said wait, one last thing and got out a black,shoulder length wig,, he put it on and stood back, well Christine, that was the first time I'd been called that so I assumed that was my name he'd given me, you do look like a slutty sissy, just one more thing and he applied some makeup I looked in the mirror and I looked just devine and actually quite feminine.
Ok let's get some photos of you and us together and for the next 30 minutes or so with his camera on a tripod he did just that, glamour photos mind you, nothing rude, well not too rude.
Photo session done, we sat on the sofa, me nervously waiting for him to make the first move, maybe he was waiting for the same but then a hand slid up and down my stockings, the sensation was electrifying and caused an instant erection. He noticed this and just continued going further and further up until stroking over my cock which had by now leaked a little pre cum, oh you naughty girl he said and continued, he did go in for a kiss but I wasn't ready for that, well not just yet but didn't disappoint later. Well this was my chance to see what was his under that dress so copied him by stroking his leg going further and further up until I got a bit of a shock as I brushed over the base if his raging hard cock, I lightly rubbed my fingers over his shaft then going to the base which I instinctively tried to wrap my hand around with some difficulty, it was large, larger than me, I then slowly worked my way up slowly, this was to put my 5 ½ inch cock to shame, it just kept going up! I guess it was about 7 inches and thick but to me still a monster for my then virgin ass.
The play got more and more intense then he got off the sofa and onto his knees in front of me and slid down my pre cum soaked panties, my cock sprang out , he gave an approving moan and went down licking and sucking just the tip. My first time and it was very difficult not to cum there and then but I guess this wasn't his first time as he knew the signs and backed off to my disappointment but he had plans and didn't want them ruined by me cumming too early.
Right, your turn, we swapped positions and copied what he'd done to me, I pulled his panties to one side to reveal the thick 7 incher, At that time it hadn't crossed my mind I'd be fucked by that as I innocently started to lick the swollen head, peeling his foreskin back to reveal the extent of his excitement with a large purple head, well bigger than mine anyway, go on he said , give it a suck, I put a little into my mouth and started to suck, no go up and down on it he said so I slowly started moving my head back and forth, not realising I'd took a little bit more in with all the excitement. I must have got carried away as he said to me, I knew it, you are a sissy cock sucker and that's when I'd realised most, if not all of his cock was in my mouth, I'd heard of people gagging at this but I didn't, maybe he was right! I am a good cock sucker.
I came up for air, this time he came in to kiss me and I didn't pull away, his tongue in my mouth flicking over my tongue lips together, it was actually ok and I guess expected from a sissy slut, ok let's go to the bedroom, I think your ready, ready for what I thought, I'd soon find out and in we went my heart thumping away with excitement.
I got onto the bed whilst he nipped out to bring his camera in, he took a few photos of me in various positions then put it down and got onto the bed with me, kicking off his heels as he did so. He unzipped his dress and slipped it off to reveal a black suspender belt and silky back panties trying their best to contain his bulging cock, the tip of that monster cock well and truly above the waistline leaking a lot of pre cum, instinctively my tongue went to it and lapped it up to the approval of my friend. His nipples looked invitingly tempting as they stood out, erect, I reached out and touched them, again his moans of approval were self-evident as he now moved position and started to rub and push against my side, similar to what I had done before accidentally inseminating him. His needs started to feel a bit more urgent as he rubbed that cock into my side leaving the odd trail of pre cum, it was perhaps too much for him as he repositioned me onto my back. he removed his panties, his cock sprung up towards the ceiling and looked very menacing indeed. He reached over to a bottle I'd not seen and applying some lotion to his rock hard cock, then something unexpected, or maybe I was praying! he grabbed both my legs and pulled me up to him and drew them both up to his shoulders, a cold feeling to my bottom as he applied some lotion to my backside, it was obvious what he had on his mind. He gently said relax, it won't hurt trust me. He then started to rub his cock up and down my then virgin ass crack, same as I did to him only this felt more sensual then he started taking shorter strokes as the top of his eager cock started to find my hole, then it found it, he stopped for a second then slowly put pressure on my hole, it refused him but slowly he applied more pressure, it started to hurt a little but was told to relax. A bit more pressure and the tip popped in, weird feeling as he stopped just inside me, maybe waiting for me to get used to the feeling, then slowly, ever so slowly he pushed into my virgin ass inch by inch, it did hurt but he was very attentive to what he was doing to me and took his time, slowly he pushed home, not bad for a virgin he said. We stayed coupled like that for a couple of minutes then reaching down to kiss me he said Ready? The pain had subsided so I nodded, not sure what to say with me being impaled on his hard cock. In small slow strokes he started to move in and out ,I guess he was gauging my reaction to it all, he'd obviously done this before given the skill and gentle fucking I was getting. No pain now, just pure pleasure, the lotion was doing it's job! His rhythmic thrusts started to get deeper into me, his balls slapping against my bum as he started to work as much of his cock into me as physically possible.
Thankfully I was tight for him as he told me later, his slow deep strokes started to get faster, his moans increased and his language, rather rude, but at the same time I found very sexy as I'd been turned into his slut.
His breathing got deeper as did his thrusts then, just before he started to ejaculate into me, he gave 4 or 5 deep animalistic thrusts, they did hurt a little but he enjoyed the look on my face and with a loud cry he came in me, a warm sensation within as his cock swelled spewing his seed into me. A few more thrusts and it was all over, his twitching cock still inside me getting softer until he was able to slowly pull out without hurting me. He put my legs back down and straight onto my aching cock that needed release, I must have been very excited as he only got to suck the tip before it exploded into his mouth, his lips clinched the end to ensure he got every last drop, I must have shot 4 good spurts into his willing mouth, one I knew hit the back of his throat as he choked a little as he wasn't expecting that from a sissy cock whore.
We gathered our breath, and panties, and just laid on the bed, he rolled over to me, kissed me, and said now you know what it feels like to have some spunk in you and we both laughed, I wished I hadn't as his sperm was slowly oozing out of me as it had with him when I inadvertently inseminated him on my first tentative steps into the world of crossdressing only a few weeks earlier.We spent the rest of the night in bed together totally exhausted from our new experience together, occasionally playing with each other, until tonight I was the apprehensive virgin, now I was hungry for more. I did wonder where this was going, a few weeks later I was to find out and my place as a sissy slut was sealed.
