This Part has plenty of action but for best results I suggest you read Part 1 first.
My drive home from the mall flew by in an instant. I had only gone there to buy make-up and ended up with a bag full of cosmetics, panties, blouse and a skirt – not to mention being sucked off in the changing rooms by the cute Asian salesman, Philip. It’s still hard to imagine that I had spent 36 years of my life without experiencing the touch of another man.
My legs were still like jelly as I rushed into the house to examine my new purchases. Drawing the curtains in my bedroom I tipped the lot out onto the bed to see everything in detail. Ignoring the eyeliner and the lipstick my gaze fixed immediately on the silky white panties Philip had sold me. Five pairs of them ranging from virgin white to cream-coloured briefs and boyshorts, just as I had asked for. And then there was also a lone thong I hadn’t expected. There was no substance to it, just a thin sheath of cloth but it had enough power to excite me in an flash.
That familiar sensation in my jeans was returning and after all that had happened that morning I wasn’t in a position to deny myself just a little selfish pleasure. Dropping my jeans to the floor I strolled over to the full-length mirror and admired the way I looked in my shirt and the stiffening package stretching my wife’s white panties. They were already soiled when I had put them on just a few hours earlier. I could only imagine what kind of state they were in now. Pushing them past my hips I let them fall to the floor. When I picked them up they felt damp so I looked at the crotch. It was completely drenched with the last of my sperm which had leaked out since my encounter at the mall. I thought my Asian boy had drunk me dry! My cum had mingled with my wife, Sandy’s, cunt juices and as I smelt the pungent aroma I couldn’t help but start rubbing my cock. I licked the panties and imagined that the wetness was a combination of Sandy, me….and Philip. And then I realised that during all that time in the dressing room I had neither seen nor touched Philip’s dick. I really wished I had – it would be another image I could masturbate to. And right now masturbation was foremost on my mind.
But before I attacked my cock I needed to continue fulfilling the fantasy that had raised its naughty head just that morning. So, laying the offending panties on my pillow I put on the white silk blouse I had tried on earlier. But which pair of knickers? They were all so alluring but for present purposes I opted for the thong. It quickly dawned on me that this was the way forward. As I pulled it up the front just about covered my tackle but having nothing covering my buttocks felt weird. The sensation of just a thin strip of cloth covering my crack and pushing against my anus was revolutionary. Tucking my balls in and my cock between my thighs I rushed to the laundry to grab some of my wife’s dirty pantyhose. I put it on there and then and the skin-tingling feel of it made me feel really girly all of a sudden.
In order to delay the inevitable I decided I would take my time getting back to the bedroom. I tried the walk. If I wanted to dress like a girl I had to act like one. I swayed my hips and strutted through the house but wasn’t convinced. I slipped on the slinky mini skirt. It felt good and it showed off my legs and the contours of my tight butt. After a couple of swirls in front of the mirror I felt like I was on the right road, the road to sissy heaven.
After a few more admiring glances at my reflection I practiced standing with my hips and my ass in seductive poses. I drew the skirt up alluringly on the hip to show part of my buttock. I bent over and lifted it all the way up to my waist so I could get a good look of how my ass might look to someone else. That was particularly horny but what turned me on most of all was the sight of my ‘pussy’ as I lifted the skirt up at the front. I just stared and took in all the possibilities. Closing my eyes I rubbed the flat of my hand over my cock and felt the pressure rise under my pantyhose and thong. My cock was trying to burst its way through as I continued the stroking.
I walked over to the bed and picked up the damp panties from my pillow and lay down fully clothed. With one hand I stroked my covered cock and with the other I held Sandy’s knickers to my nose. With closed eyes I began to re-live my morning seduction and blowjob. I thought of Philip and how he had been so surprised and turned on by me wearing my wife’s underwear, how he had kissed me sensually and how good his mouth had felt around my penis. With these thoughts running through my head I was compelled to act. I hitched my little skirt to my waist and in one action removed my thong and pantyhose. I placed all my attention on my rigid cock. Running my finger over the tip it was obvious how aroused I was. An endless stream of pre-cum seemed to be oozing from me. I bathed my hand in it and smeared my shaft all over before wrapping my fingers around it.
Its slippery feel was like Philip’s mouth all over again and the thought of him sucking on me nearly made me burst on the spot. I had to slow down, but another smell of Sandy’s panties reactivated my pleasure and I began to wank with more vigour. I spread my legs and brought my knees up so that anyone looking would have had a perfect view of my puckered anus. I squeezed some of the free-flowing fluid from my dick onto my middle finger and guided it my anal gateway. I rubbed it around the crack, adding more fluid every few seconds until my ass was almost overflowing. I couldn’t take any more of this teasing. I had to replicate Philips’s finger action before I came. Gliding my finger slowly over my anus, I gradually began to work it up my passage. It was tight and invasive but the more I thought of Philip doing it to me that morning the more I began to appreciate the pain sexually.
Once past my sphincter it felt like I was ready for more. As my cock was being milked energetically it felt like a good time to up the ante. With a little more lubrication I started working two more fingers into my ass. It was awkward but it didn’t take long to discover that stuffing my hole as much as possible increased the pleasure enormously. Soon I was stretching and relaxing my anus in time with my wanking. Before long it felt like I was being sucked and fucked all at once. Momentum was building quickly and the only thought I had in my head was of Philip pounding my ass while his twin was taking my hard cock down his throat. I unceremoniously thrust in a fourth finger and opened up my little butt as far as I could. My body couldn’t take any more. My hips and ass involuntarily lifted off the bed and my cock shot forth a stream of cum with the first batch covering my mouth and cheeks. It felt like I was having one orgasm after another as sperm spattered my new blouse. I couldn’t help myself, I licked all around my mouth to taste my own cum. There was so much of it. Despite the acrid taste it was strangely erotic and I scooped up what more I could find and gulped it down with passion. Wow, life was good.
After my spasms had subsided I realised I still had four fingers in my ass. Removing them slowly I felt what I can only describe as a great loss – not for my fingers but for my ass. In my ecstasy it had been stretched so far that I could have fit a ping pong ball in there with ease. And even then I reckon I could have fit something bigger.
My mind was made up. I knew what I had to do. I reached over for my wallet, dug out Philip’s number and picked up my phone. The SMS I sent him read, “If you still want to help me with my make-up (!) I’ll see you at 10am tomorrow.” In less than a minute I had my first official date with another man.
Once I had showered and tidied up I spent the rest of the evening on edge. Sandy came home at 6 as usual and I just didn’t want to be around her in case I let something slip or looked guilty for that matter. The fact was, I didn’t really feel guilty as such, a little dirty, sure, but I came to think of it as my right. The right to explore my sexuality. But the sneaking around, the women’s clothes, the make-up – the consequences of being found out certainly made me nervous but not as anxious as meeting up with my beautiful Asian boy the next day.
I slept fitfully that night. I dreamed up scenes of how things might play out with Philip. I re-enacted scenes from that morning in the dressing room. This whole thing was going to alter the course of my life but it just had to happen. I would forever wonder what could have been.
Sandy and I went through our habitual morning routine then she left for work just after 8. I sent an SMS to Philip for directions. Moments later he texted back and ended the message with “looking forward to seeing you Samantha.” Oh yes, let it begin, I thought. In the shower I started to get into the role of Samantha. Trying moves to look sexy, wondering what kind of positions a guy wants to see a woman in. Despite all the girls I had been with in my life, this task wasn’t easy. I would just have to make it up as I went along.
Remembering the way Philip looked at me when he saw me in my wife’s knickers was reason enough for me to slip on another cream-coloured pair for him. That was the only item of woman’s apparel I sported. I also packed a fresh pair just in case, my new skirt and the cosmetics I had bought. I borrowed a pair of my wife’s sheer white stockings and one of her blouses since I had cum stains all over my new one. I didn’t have shoes but that was the least of my worries. I threw everything into the car and took a deep breath before I turned the key. Now
I was nervous.
As I approached his house I slowed down, allowing myself the time to decide whether I was going ahead with this business or not. Theory is all well and good…. Hell with that, I knew I wanted it more than anything just then. I parked the car, grabbed my bag and pressed the front door bell. No turning back now.
My heart stirred as I heard someone on the other side. The door opened wide and there was Philip who greeted me with a warm smile. He was barefoot and wore only a tight t-shirt and a pair of white body-hugging boxers. Before I even walked over the threshold he caught me checking out his bulbous packet. Once he shut the door he took my bag, dropped it on the floor, put his arms around my waste and kissed me on the lips as if we were frequent lovers. He tongued me briefly before pulling away. “So, shall we make you a woman today Samantha?”
“Yes…..please.” I replied shyly. He took my hand and led me to his bedroom. I somehow expected a pink room with mirrors but the only feminine part of his room was a dressing table with a few cosmetics on it. Now it was my turn to see him
in a different life. He noticed the surprise and said, “Sometimes I like to look pretty too. After all I spend most of my time in the cosmetics department.” I nodded. Without beating around the bush he told me to take my shirt off and sit down at the dressing table. We were going to do the make-up first. I did as I was told.
Philip got a hairband and placed it so that my whole forehead was exposed and then he began to apply some powder to my face. As if we were in the mall he started to explain what he was going to do. I drifted off and began to concentrate on something else. He was standing right beside me and his groin was at head height. I couldn’t take my eyes off it. The day before I saw his erection through his trousers and had wondered how such a slight guy could be packing so much. Now with him clad in just a pair of tight boxers I could see the outline of his soft cock. It must have been 6 inches long. What would it be like hard? Instinctively I reached out behind him, placed my hand on his ass and drew him gently towards me. Stopping what he was doing I brought my other hand up and placed it gently over his covered cock and began to rub it gently. In a matter of seconds the contour of his knob end became clear and before long the whole thing was pushing its way towards me. I turned around in my seat to face him full on and slowly pulled his shorts down over this massive bulge. His cock sprang to life and pointed skyward. It was huge, it must have been almost 8 inches long and thick like a tree trunk. And it was cut, just like my own.
I immediately got this slightly sweaty, musty smell which made my own cock push against my new panties. Intrigued and horny I cupped his heavy balls with my left hand while my right went straight for the shaft. He let out a long moan but said nothing. I bent his dick forward a little and brought my mouth close, breathing in his manly smell. Just the aroma of him turned me on. Venturing into new territory I bent forward and licked the clear fluid from the head and savoured it in my mouth. I couldn’t describe it but I wanted more. So I took his purple head into my mouth and tasted him properly. It was heaven but I couldn’t wait to see how much I could fit in my mouth so I began to slide my lips up and down his length. My mouth was stretched wide and I could feel I wasn’t getting very far. I wanted it all but it just wouldn’t fit.
Then I heard, “Open your throat and let it just go down. Don’t try to breathe at the same time.” Without budging, my lips continued to slide over his shiny cock and then I tried to go a bit further but gagged. After a few more attempts I got the hang of it. His 8 inches were slipping in and out of my throat and I still wanted more. I simply couldn’t get enough of him. I relieved my left hand of his balls and unzipped my own jeans and after some fumbling had them, and my panties, down at my ankles. I continued to take Philip’s cock down my throat as I vigorously wanked myself. Between his ever-louder moans and my slurping we were both getting worked into a frenzy. It was mind-blowing.
All of a sudden Philip softly lifted my head off his cock and said, “Samantha darling, we should take it easy for a few minutes. We don’t want to spoil the moment.” I was crestfallen because I so desperately wanted him to come in my mouth. “I’ve nearly finished making you up. And then,” he paused, “we can get you dressed like a pretty little sissy.” He hit the spot. Despite my arousal I knew I had to wait for that. I reluctantly gave in and let him finish the job. When he had finished he took off the hairband and as I took a good look in the mirror I really did look very feminine but, sadly, still a man who looked feminine. I had wanted to be mistaken for a girl on a busy street. Nonetheless I still found myself quite attractive. After all, there were still the clothes to put on.
By the time Philip had finished the make-up my cock was soft and I needed to piss. When I said this he frowned, “Girls pee Samantha, they don’t piss.” I felt admonished as he took me by the hand to the bathroom. As I lifted the seat, I heard “Girls sit down when they need to pee, don’t they Samantha?” I enjoyed obeying him. There wasn’t much I could do since I was now completely naked and feeling vulnerable. He had his shorts back on and was in complete control.
I returned the seat to its position and obediently sat down. I was told to put my dick down between my thighs and keep my knees together. When I had done what Philip asked I realised it looked like I was a woman, just a little mound with no penis. I found it hot and judging by Philip’s look, so did he. It took a few moments before my bladder acted but when it did, I felt great relief but this time it was also sexual. My piss kept coming as Philip dropped to his knees in front of me. I was in full flow when he parted my legs to look at me peeing. He held one hand at the hilt of my cock to keep it down until I had started to finish off in spurts. Before I could spray him he grabbed my flaccid cock and shoved it into his mouth where I drained myself into him. When I had finished he sucked and licked me clean before swallowing the last mouthful.
He did nothing for a few seconds, allowing me to get hard in his mouth. He let me fuck it briefly before pulling away, leaving me sitting on the toilet with a giant boner. “I hope you’re still in the mood, my love,” he said before taking my hand once again. I was more than in the mood. When we reached the bedroom he took my bag and emptied it out on the bed. It was time to get dressed up like a pansy and just thinking about it was turning me on.
Philip picked up the panties I wore to the house and handed them to me. Then he laid out the pantyhose, skirt and blouse on the bed. “Get dressed now and I’ll be back in a minute,” he said before leaving the room. As I looked at the girly clothes I started to get aroused all over again but I knew that if I wanted to fit into my panties I couldn’t afford another erection although I did permit myself a feel from my anus to the base of my cock. I was completely hairless down there and it felt so alluringly smooth. I refocused on getting dressed and while I was luxuriating in the sheer silkiness of my new clothes I was getting more excited with each item I put on. Standing in front of the mirror I zipped my new short red skirt up at the back and then without thinking I did a lovely girly twirl to see how pretty I looked. Jesus, I really was enjoying this new obsession of mine.
As I was admiring myself Philip walked in and gave me a very approving look with wide eyes. “Wow Samantha you look so hot…… but you could look even hotter. I have a surprise for you”. From behind his back he pulled out a woman’s wig with dark brown hair. Fuck me, I thought, I really am going to look the part. He beckoned me over to sit at the dressing table. Standing behind me he placed the wig over my hair and made a few adjustments until he was happy with the fit. I looked aghast at the reflection, I didn’t recognise the woman in the mirror. She had perfectly straight shoulder-length hair and a perfectly straight fringe which fell to just over her eyebrows. It was the kind of hair that could sway freely and you could keep it out of the way by tucking it behind your ears. After Philip gave it a brief brush I got up and looked at myself. It was no longer me. I really was becoming Samantha and if I could have I would have fucked myself there and then.
And given Philip’s gaze it looked like that precise thought was on his mind too. With a pat on the ass he told me to follow him into the living room. “I want to admire you for a while,” he said. I was a little disappointed but at the same time it gave me more opportunity to stay dressed as Samantha. I sat down on the couch, and conscious of my new persona, kept my legs together and slightly to one side so there would be no peeking up my skirt. Philip perched himself in the armchair directly opposite and then produced a massive joint from a drawer in the coffee table. “This will take your mind off any guilt or reservations you might have.” It had been years since I’d smoked grass but I knew he was right. He sparked it up and after a minute passed it over. I took it willingly and within a matter of minutes I did feel relaxed but I was also feeling decidedly wanton. I was also becoming uncomfortable sitting like a prudish girl and wanted to cross my legs. So I did, but not without giving Philip a good look at my panties in the process. From then on he couldn’t keep his eyes off my legs and skirt. It was so obvious that he was getting turned on as the bulge rose in his boxers. So after a few minutes I crossed them again but took more time about it. That seemed to tip him over the edge. He got up, held out his hand for me to take, and led me back to the bedroom.
Once there he placed a hand on my ass, drew me to him and kissed me passionately. I could feel his stiff cock press against my inner thighs which made my own start to pulse between my legs. Thankfully my tight panties were holding it in place. Then he asked me to turn around a couple of times for him. “Wow Samantha you really have turned into a very pretty girl. Do you know what I do to pretty sissies like you?” I had a fair idea but nonetheless replied, “I don’t know. Why don’t you show me?”
At this he stripped off his shirt to reveal a lean chest. It was hairless and I could see his nipples were erect. Never before had the sight of a man make me stir as I did that moment. Philip urged me to the edge of the bed facing inward while his hands slipped around my waist from behind. He still had his shorts on but I could feel his cock lying against my ass. He raised his hands and caressed my nipples through my blouse. This was it, I thought, this was the moment I had been waiting for. Expertly he unbuttoned me, his hands taking in every inch of my torso. I stood there generating a massive erection as he started to move his hands up and down my hips. It was so sensual, so moving, loving almost. I closed my eyes waiting for him to go further afield and it didn’t take long. Without hitching my skirt up he managed to weave his hands around to my inner thighs and I spread my legs a little to give him more access. The sensation was fantastic and I was getting more turned on by the second. He must have spent two minutes just teasing me with his fingers slipping occasionally inside the seams of my panties. I just wanted him to get on with it but I knew the real fun was in the waiting.
When Philip felt I was suitably aroused, he moved his hands upwards and said quizzically, “What do you have here Samantha?”
“Something just for you my love,” I uttered.
He placed one hand over my panties and added, “I think you’ve been hiding something from me. I’ll just have to see what it is.” He lowered my panties and I let them slip to the floor before stepping out of them. He replaced a hand and grabbed my cock by the shaft. “You’re a naughty girl Samantha. Shouldn’t you have told me about this before?” To which I could only reply, “I wanted to surprise you darling.”
He moaned his approval and began stroking my hugely erect cock while his other hand started fondling my balls. With all this attention I found it hard to continue standing so I leant forward and put my hands on the bed. This appeared to excite him as the next thing I knew was a defined cock rubbing itself up and down my ass crack. He must have taken his boxers off while I was moving forward. Smooth. He kept on stroking me slowly but took away his other hand and within seconds I could feel something moist running back and forth over my anus. Raising my eyes to heaven I let out an appreciative groan. Over the next couple of minutes it got wetter and wetter and I began to bathe in the pleasure of grinding up against it. All of a sudden his finger was replaced by something much, much bigger.
Philip pulled up my little skirt and held it up against my back. He leant me forward a little more and then I really felt something. This was it, this really was the moment. The head of his cock was trying to invade my anus and while my lust required it, my body didn’t want to take it. “Just relax. The first few seconds will be the toughest but after that you will love it.” After a few more rejections I gave into the pain as his thick head passed my sphincter. The pain was immense and thank God he paused to let me adjust to his enormity.
Once the agony passed I breathlessly muttered ok. Philip slowly moved his monster further inside me until it seemed like it was half way up my colon. Once fully in he stopped and asked how it felt. “It’s immense my love. Be gentle with me.” Without saying a word his cock began to move in and out slowly and I began to moan in response. Before long I was revelling in being stuffed like a pepper and began to grind my ass to meet every thrust. The pace picked up and I moved with it. He brought his hand around and grabbed a hold of my cock and continued where he had earlier left off. With my ass and dick being stimulated at the same time I couldn’t help but groan loudly with pleasure. I so desperately wanted to come but couldn’t let myself, I knew the feeling wouldn’t be the same after that.
I needed a respite. With difficulty I pulled away from Philip with regret, feeling his huge cock leaving my ass. I threw myself into the middle of the bed, lay on my back and put my legs in the air. Fuck me like a woman I said to him. Give me a proper seeing to, I’m not going to last much longer. As he climbed onto the bed, his massive penis extended before him, I placed a hand on either side of my ass to stretch it in anticipation of his arrival. I soon realised I didn’t need to, he had already stretched it to such an extent I didn’t think possible. What a turn on.
He got into position, grabbed my ankles and pushed them back towards the wall and impaled my ass with such force I thought I would come right then. With my blouse, skirt and stockings still on, not to mention the sexy wig, being shafted by a cute gut with a big dick, I really felt like a woman. My briefly flaccid cock had returned to life and I wanked myself in time with Philip’s thrusts. My whole body was moving with the strength of his thrusts and the fuller I felt the closer I was to coming. Philip pushed my ankles back as far as they would go and leaned in closer to kiss me, sweat dripping from his face. The intimacy drove me to the brink. “I’m going to come any second. Come with me,” I urged, still pumping away at my cock. He went faster now and I began to pant like a dog. As his balls smacked against me and as his cock pounded me harder than ever, that familiar sensation swept over me and I screamed, “I’m coming baby, I’m coming.” My body went rigid and a few seconds later spasm after spasm hit me, cum flying out of my cock like never before. My nipples and stomach were being covered by a sheet of sperm. I sensed the cock deep in my ass get wider. The gush of fluid being injected deep inside me seemed endless and I screamed again in boundless pleasure. My as felt full. It was. No woman could ever replicate this kind of sensation. Man on sissy was the way it had to be from now on.
It took a while before my body began to relax. Philip was still inside me. I cupped my hand around his neck and kissed his sweaty, panting mouth. “Thank you my love,” was all I could say. The feel of his cock wilting inside me was both sensual and regrettable. But as I sensed the cum leaking out of my ass I knew I’d be back for more.
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