After that memorable night where my friend unexpectedly dominated and sissified me, I wanted more.We now met on a regular basis and we're more daring with each other, well mainly him!. By now my then girlfriend had moved away to university so I had ample free time to be Christine and made the most of it dressed when at home, it felt so liberating and sensual. My friend knew this and made full use of my new sexual freedom. I got a text from him late Thursday asking if I could come over Friday as he had a surprise for me ending in XXX. Intrigued with the message I replied ok wondering what his surprise was, maybe he'd bought me a dress more befitting to my new found sexuality?
I arrived on Friday, eight o'clock prompt as I normally do, knocked on the door, it opened and what a shock, was this the surprise mentioned in the text?
Standing before me was my friend, dressed in a black wet look dominatrix outfit, more befitting his now dominance over me. His rampant cock pushing the short hem of it outwards, a sudden stiffness in my boxers was a good sign! So this was the surprise I asked? partly he replied and ushered me into the flat which looked slightly different with the soft lighting.
Ok he said, there's something we'd like you to wear tonight, hope you like it, it's on the bed. Caught up in the excitement it hadn't registered what he had just said with the ‘We’ bit but just did as I was told and made my way to the bedroom Once in the bedroom, on the bed I saw the usual, stockings and suspenders, some very see-through panties that left nothing to the imagination, a very nice silk pleated skater skirt, yes I really liked that and a black satin blouse, finished off with the shoulder length blonde wig. Okaaaay, not my usual dress but being the sissy slut he was turning me into I didn't say anything. I took a shower to freshen up then I slowly put my clothes on and to be honest, I looked very sexy indeed! Here he said, let me make you up, I hadn't quite mastered applying makeup so thankful for that. He also applied some black nail varnish, another first for me.
When finished I looked in the mirror and, well,I looked very slutty indeed! , my friend rubbed his hands up and down my sides, saying ' you'll do' and gave me a soft kiss on the lips which had the effect of stirring my sissy cock into life again. I was wondering what he had in mind for tonight, the thought and anticipation was now getting the better of me as I wanted him to take me right there and then.
Calming down a little we had a coffee and chatted about stuff then the conversation came round to threesomes, I did admit in the past to him I'd always thought of that with him but never had the courage to ask but tonight was going to redress all my doubts I had about this.
Well he said, the surprise I have is for us to be joined by a friend of mine who's taken a shine to you . He saw the photos I took of you and asked if he could meet you. My heart jumped a few beats, someone else knew my secret, a sudden panic then the realisation that one of my fantasies I'd dreamt about was possibly going to become reality. If you don't want to, I can call him and tell him not tonight, take your time, in a flash I said yes! Oh my god, what a slut I've become! I thought to myself.
He told me the clothes I was wearing tonight were by request of his friend, hmmm I thought , I'd been set up! But more excited at the fact I'd be the centre of attention of two horny cocks and the realisation that one of my fantasies I'd often masterbate myself to in the past was possibly about to become a reality, never in a million years would I'd of thought it would be with my best friend.
About 9:30, there was a soft knock at the door, My friend went and let his friend him, they kissed passionately before saying , this is Steve, he was mid 40's, about 6 foot , athletic build , shaved, head wearing a pair of trousers that were either a size too small or he had a very large cock judging by the outline, a moment of panic came over me as my friend was large and sometimes i found it difficult to accommodate him but this!! he came over and gave me a peck on the cheek, stood back to admire me and said what a beautiful Sissy I was and felt my bottom through the silky skirt making it glide over the sheer panties and stockings underneath, I'll be honest with you, It felt good, REALLY GOOD, the material of my sheer panties desperate to keep my small yet rock hard cock contained within. I closed my eyes as his hand rubbed over its length, I opened my eyes to see him looking directly at me, my face burning red, initially with embarrassment as he complimented me on how hard it was and the fun they were going to have with me. At this moment I didn't know if I could go through with this as fir all intentional purposes, Steven was at this time a complete stranger but my friends presence gave me that reassurance I needed.
Steven also complimented me on my photos, and explained it was him that developed the photos. Being an amateur photographer, you really didn't take these kinds of glamour shots to your local chemist to develop! We all laughed at that which broke the ice and I felt more relaxed.
I did wonder when my friend said about him seeing the pictures he took of us that night, mystery solved.
By now, introductions over we now sat on the sofa, me in the middle with a glass of wine watching a video of a crossdresser threesome and started to get excited I could be the centre of attention tonight and wondering what they had in mind which made it the more Intense for me as my panties were now beginning to show signs of pre cum oozing through the very see through material yet to be revealed by the pair. As we watched the video a hand rested on my stocking clad knee, quickly followed by another hand on the other knee. Rythmatical, they slowly stroked along my legs, the feeling for me was ecstatic, more pre cum started to slowly ooze out from my cock and through my panties. Steve couldn't resist it any more and moved in for a kiss whilst now stroking my erect nipples through the silk blouse. I reacted positively which encouraged him to be more daring with his exploration of my body. Several months earlier I'd not even considered kissing another man but here I was, passionately exploring his mouth as our tongues flicked over each other. My friend had now moved his hand up and over my skirt, it felt amazing as the skirt slid against my stockings as he did so. By now my cock was straining to burst through my panties, I'd never been so hard or excited, what a slut I was and they both knew it.
Steven broke off teasing me and stood up in front of me, he removed his shirt to reveal a nice toned body, then he undid his trousers and they slipped down to reveal he was wearing hold ups and a pair of ridiculously small red panties that had no chance of containing his large cock,bigger than my friends, it was sticking out the side, quite a lot if it! a sudden fear and excitement of the prospect of being impaled by it swept over me, there was no going back now.
Once his trousers were off he knelt down in front of me, running both hands slowly up my legs until under my skirt, he lifted it up to reveal my panties with a large damp patch on them, he made a moan of approval as his hands now moved over the damp patch spreading my pre cum over my still pantie encased cock. He slid his hands up to my panties waistband and hooked his fingers over them then proceeded to pull them down, my cock, swollen and painfully hard sprang up and slapped against my belly, Hmmm he said, looks like you need some relief as he slipped my panties off. He repositioned himself to the tip of my cock, still moist with pre cum from their teasing. My friend now undid my blouse and was rubbing and sucking my nipples, I was surprised I didn't cum there and then as I desperately tried to hold back the best I could. However, Steven had other ideas about that and slowly started sucking the top of my cock. The sensation was making me tremble with excitement, then he started to lower his head , taking more of my small sissy cock into his mouth. Holding the base he started in Earnest to milk me, it felt amazing, compared to my friend he knew all the tricks in the book, I tried not to cum but he knew what he was doing and within a couple of minutes he got his reward as I shot, with some force, into his mouth and down his throat. He spent a few minutes making sure he got every last drop of spunk out of me. My arousal hadn't stopped though, my friend was still playing with my nipples, twisting them, sometimes quite hard, then stroking and sucking it felt wonderful
This had the effect of getting me aroused again quite quickly.
Steven took his chance and got me onto the sofa on my hands and knees, head facing off the back of the sofa . He positioned himself behind me , lifted my short skirt up to my waist and pushed my legs apart to gain access to my now willing body. He put some lube in my crack and slowly inserted his fingers, one at a time to stretch me a little to make his entry as easy and as pain free as possible. He managed to work 3 long, thick fingers into me, moving them about inside me whilst slowly moving them back and forth until I guess he was satisfied he could get his 8 inches into me. The time came and he started to rub his cock around my bottom until he found my hole, he pushed to try and enter me but my still tight sphincter refused, he tried again with a little more pressure, still he couldn't penetrate me, a little more oil applied to his now hard, and swollen cock he tried again, ‘ relax baby, daddy will be gentle with you’ I hadn't been spoken to like that before which momentarily took my mind off what steve was trying to do with me, another push, this time the head opened me up just enough for it to pop in, now he slowly tried to shove that monster into me, my body tried to deny him but his persistence won through and slowly, if not with some discomfort, inched his way in, pain slowly subsided as he drove that monster home and stopped there so I could get used to him, his hairy balls now pushed against my bottom.
Meanwhile my friend had positioned himself in front of me and offered his cock to my willing mouth which devoured it as deep as he could push it in. Oddly enough I did gagg on that occasion but he pulled back a little so he could start to slowly fuck my willing mouth whilst Steven started to slowly pull back then in again. Quite pleased with this as it was my first spit roast and I was now starting to enjoy it being the attention of two horny cocks looking to seed me, an experience that would shape the rest of my life.
Whilst my friend was fucking my mouth at a steady pace, Steven was a bit more erratic, slow thrusts deep faster thrusts making my little cock swing in time with his thrusts, enjoyable all the same, my friend was about to seed me , he moaned lightly as the head of his cock swelled and the tip started twitching releasing my prize, he held my head as the first powerful spurt hit the back of my throat making me swallow immediately, then pulled out to cover my face, his sperm now slowly dripping down towards my lips and chin, what a mess he'd made of me! I'll always remember that smile on his face as his moved back to watch me now being fucked by his friend.
I prefer to savour the taste and texture of my friends creamy sperm but on this occasion, he denied me. I was becoming their cum slut and they were going to use me as such. On seeing this, Steven changed his pace again slightly faster and now gyrated his hips with each thrust to try and stretch , which was essentially, my still a virgin hole for larger cocks. He pushed as deep into me as he possibly could, this was causing me a mixture of pain but also a pleasure I cannot describe. His pace increased, then he made a loud noise, indicating he was about to flood me with his sperm. His last thrusts were hard and frantic before finally he came deep inside me, slight pain again as I'd never been penetrated that deep, then another loud shout as the first spurt of cum was Injected deep into my now sissy compliant little body , it felt warmer than my friends, perhaps a combination of his rough excited fucking of me and the soreness he caused as i was stretched to accommodate his larger cock.
His cock now twitching away as it continued to pump his sperm into me , the warmth of his sperm very evident now as it was pushed further into me with each hard thrust, Steve grabbed my hips tightly as the another powerful jet of sperm shot Into me, then another and another, I can only describe it like a grease gun pumping away inside me! It didn't feel real, he just kept coming in huge spurts! I counted 6 then a few more smaller ones. This man had flooded my sissy body with his sperm, none had leaked out so either we had a perfect coupling or he had really spunked deep into my body.
We stayed coupled together for a couple of minutes whilst Steve’s' erection subsided and my friend got a towel to catch any spunk that might leak out as Steven withdrew. Slowly as he did, some sperm came out but not what they were expecting, why?, were they expecting a torrent of sperm? They knew something! I went to the bathroom to clean up, my makeup smudged and with dark streaks of mascara down my cheeks, then it happened, his sperm slowly starting to leak from my still gaping hole, not just a dribble, but quite a lot which ran down my stockings, now laddered and holed by Steve as he held me tight whilst he came into me. I wiped it off but more replaced it. Several attempts later it had slowed down but still leaking, was this how my friend was when I'd accidentally inseminated him all those months ago? Looking at the mess it was making of me I wondered just how deeply Steven had inseminated me. Whatever the answer, I'd actually enjoyed it, my fantasy played out, now I wanted more, now I really was becoming that sissy slut my friend enjoyed so much.
I went back out to see them back on the sofa waiting to see their handiwork, my stockings with a stream of spunk still down my inner thighs and my makeup ruined by my friend's spunk still sticking to my face. My friend quickly grabbed his camera and shot a few of me in this dishevelled state, Steve made a comment about my appearance and how his friend would have loved to witness this, that remark didn't go unnoticed by my friend who gave him a real glaring stare. My friend asked me , did you like our surprise then, thinking it was the spit roasting, a term until now I'd never really heard of. I said yes, then the penny dropped as he told me Steve is a very heavy cummer as you've just found out.
Steven stopped a while and chatted to me about things he liked and what he'd like to do with me which made me blush and aroused at the same time but I was too tired and a little sore and wasn't up for a repeat performance so he bid his farewells and left, leaving us alone. I slipped on a long nightie and shared the bed with my friend as I didn't want to be on my own that night, so much had just happened to me and I guess I needed someone just to cuddle up to whilst I tried to figure out if I'd done the right thing , the fact my bottom was so sore I couldn't really walk far was maybe another factor! Yes, Steven, a man twice my age had really used me and I enjoyed it! , I think that was the turning point for me as my preference for older men over the years would become a common factor.
We got up next morning and I was still leaking some of Steve's cum , a damp patch on my nightie gave it away, my friend patted my bottom and laughed, ‘told you Steve's a heavy cummer.’ I laughed back and wondered what Steve had planned for me, it didn't take too long for the answer and my journey into the world of the sissy submissive slut gained momentum and recognition from other people just like Steve who took an interest in me.
To be continued
