Holidays with Peggy my wifes sister part2
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Boys Will Play While The Wife's Away (Part 1) free porn video
The thing about being married is that life really isn’t easy. It’s a matter of diplomacy most of the time and, yes, diplomatic relations sometimes break down. Under normal circumstances it’s not often a positive sign but I’ve since discovered that in my own realm it really can be a revelation. At the beginning of my wedded life this was not so conspicuously obvious but as time went on and as marriage posed its usual problems and inevitable hurdles, things changed. And not in a way my wife would have appreciated. But in my world marriage offered up new opportunities and I seized them with all the hunger of a man denied the endless possibilities dictated by the social norms of his upbringing.
Standard procedure when things get a bit bumpy is that you fix them. That’s the decent way and I adhered to it avidly during the first few years with Sandy, my pretty and rather sexy wife. We got hitched when I was 32. Four years my junior I had initially become mesmerized by her at an informal dinner party my various friends and I used to give once a fortnight. A tall, slim brunette with beautiful long legs she tantalized me for months with her short skirts and body-fitting blouses which showed off her tidy ass and small but firm breasts. It took some time and numerous dinner parties before I ever had the chance to ask her out. When I did, things just clicked.
We didn’t move in with each other for over a year. When we did, it was tough since I had always been known as, and felt like, the eternal bachelor. These final 12 months living on my own allowed me to stray on a few occasions with other women but while there was satisfaction, it singularly proved short-lived. All of these dalliances were with women who looked just like Sandy with similar figures and similar looks. None could match up though. We eventually tied the knot.
I won’t hide the fact that the initial period of co-habiting was difficult. It was excruciatingly awful at times but making up seemed to make things better. It seemed to make us stronger. It was at these moments when we really discovered each other sexually. It was as if we had been through such trauma that we were permitted to let ourselves go and to explore each other without inhibition. Those times were great but there are fewer of them now. I can’t and don’t blame her. You see, I found a new outlet for my frustrations or, rather, let’s say, I discovered a new outlet for dealing with matters which allows me to think of something aside from domestic issues.
Sandy is a secretary with a secure job and I’m a would-be journalist who’s had little success. Still waiting vainly for the big break I suppose. Anyway while she’s at her 9 to 5 job I find myself roaming around the house finding any excuse not to sit down at my desk. So I do the washing up, the tidying, vacuuming and the laundry, just like a house husband. I hated these chores. It wasn’t until I was doing the washing one day that my life changed. Sandy always insisted that I separate the whites from the colours so this particular day as I was making two piles I noticed that the whites pile consisted mainly of her knickers, bras and those sexy leggings that she often wore. What made me pay attention to this I can’t say but it certainly got my attention.
I picked up a pair of her simple white panties, turned them inside out and looked properly for the first time at the crotch stain. Where once it had been moist it had now hardened. I lifted it to my nose and breathed in. It was magical. Sweet yet not. I couldn’t put my finger on it but one thing was sure, it stirred something in my boxers. Something told me I was bordering on being a pervert but, ignoring that, I kept going.
What would it be like to put the panties on? I had taken the first step, why stop now. The laundry has no windows so I was safe. Sandy was at work. Who’s going to walk in? Feeling like a deviant I dropped my jeans and boxers to the floor and slipped the simple white panties on. It took a minute to adjust myself to the new fit but I liked the feel. It’s hard to describe precisely what I felt but it was liberating. Compared to my own underwear it was light, comfortable and, above all, sexy. I looked down at myself and saw a pronounced defined bulge which showed off the contours of my hardening dick. Unlike my own baggy boxers, these panties kept my cock pointing downwards with no room to move. It was pushing the crotch away from my body so I spread my legs and pushed it back, along with my balls, between my thighs before closing the gap again. Jesus, it looks like I have a pussy, I thought to myself and that sent me over the edge.
Such a sensation was new to me. I felt sexy, not in a butch way, but in a gentle, feminine and soft way. It felt so good. I ran my hands over the front of the panties and imagined I was touching myself as a woman. I closed my eyes and reached under my shirt to fondle my nipples as the other reached around to feel my ass. In a matter of seconds I was standing in only a pair of my wife’s underwear pulling out a bra, blouse and a pair of those sheer white leggings from the pile.
I took my time getting dressed, wanting to savour every minute but still eager to look at myself in the mirror. Apart from the bra everything felt so comfortable and warm against my skin. I was in such a state of arousal that I ran from the laundry to the bedroom. Closing the curtains I turned on the light and admired the reflection in the mirror. I looked hot and took pleasure in the prettiness of the vision before me. Nothing in my life had prepared me for this moment. The endless possibilities rushed into my head but I quickly realised there was only one thing I really wanted.
Over the next few days I repeated my actions but improved on them each time. I started by trimming my pubes so nothing would stick out the side of my panties and even used my wife’s hair removal cream to take care of the hair from my balls to my anus. By the time I was finished this area was silky smooth and very sensitive to the touch. The enjoyment of looking girly was turning me on so much that I thought about using make-up but was sure that if I used Sandy’s she would notice.
So for the first time in my life I left the house wearing soiled panties and a pair of my wife’s pantyhose, covered up by my habitual jeans. It felt so taboo and unless I got knocked over by a bus, it would be just me who knew my dirty little secret. Even though I was a bit scared venturing out of my comfort zone, the feeling was delicious.
In order to avoid meeting anyone I knew on my clandestine shopping trip I took the safe option and decided to go a bit further afield to a mall about 30 miles away. There was less of a chance of being spotted. All the way there I was getting more and more excited but also more and more nervous. I wasn’t sure if I could go through with it. What if I get caught? How would I ever explain it to my wife? I could never expect her to understand or even accept what I was doing. And frankly I would never be able to look her in the eye again.
As I was mulling these thoughts over in my head I suddenly found myself in the cosmetics department. I also realised that my knickers had bunched at the back and were now stuck in my crack. It felt so hot and was also a good reminder of why I was here. The problem though with these places is that you can’t browse without being accosted by a, more-often-than-not, salesgirl. Getting this far was one thing but having to tell somebody what I wanted was yet another, and all the while pretend it most certainly wasn’t for me! To my utter surprise the first person to come up to me was a small Asian guy of about 20 with a walk that was more suited to a catwalk. His hips swung as he approached me and while he began to smile at his potential new customer I noticed he sneaked a furtive glance at my groin. I have to admit I was a little turned on by this; it wasn’t every day that another man gave me that kind of attention.
Damn it what do I do? How do I play this? Not one thing had I thought through. Here I was trying to advance my sissy perversion and I was faced with one of those weird situations that life throws your way. “Hi”, he said. “Hey. Em, I’m looking for some simple make-up…..for a play I’m in……Pygmalion”, I added. He looked at me with a smile. “Sure”, he replied knowingly, “I can help you there. You’ve come to the right place. Philip’s my name and I can assist you with whatever you need.”
He played the game like a pro but by the time he had finished selling me cosmetics I felt that making myself up might be more time-consuming than my wicked desires could bear. “Which part in the play do you have?” I couldn’t remember Eliza Doolittle’s name so I had to improvise. “Em, just an extra…..one of the promiscuous street types”, I replied. “It’s an amateur dramatic society so we have to provide our own stuff.” I added for no reason at all, “I even have to get my own dress.”
“Well, that sounds like fun,” he said. “You’ll need to feel comfortable with all that on. Do you need any underwear for the part?” he asked without missing a beat. “As a personal shopper I can bring you anywhere in the store.” He was complicit, I knew, but I still had doubts. Hell, I’d gone this far already. “What a good idea, why not.” With an about turn he commanded, “Follow me.”
I did as I was told as he led me up two floors. It was hard to take my eyes of his skinny little butt. He moved like a woman in men’s clothing and there was no doubt at all about his sexuality. It was hard to admit it to myself but I found him cute. His knowing looks, his understanding of my needs and his willingness to please were all a big turn-on. Not to mention that he was about to confidently sell women’s underwear to another man. I was a novice in the presence of one who truly wasn’t.
When we arrived on the second floor he asked me out of the blue if I knew what kind of panties I liked. A bit too quickly I told him briefs and boyshorts, thinking of my wife’s which I had already sampled. Nothing too slutty. And white. He didn’t need to ask my size. Firstly I had no idea of women’s sizes and secondly he had already sized me up enough to already know. I was told to wait over by the changing rooms and he would be back in just a few minutes.
Doing as I was told I couldn’t help but take in the selection of clothing along my short trip. Men don’t have that much to choose from, I thought. Lucky girls, I thought to myself. It wasn’t hard to see how they could begin to seduce a man. My mind began to wander but was quickly brought back to the present by the sight of Philip with an armful of clothes. He must have had a dozen pairs of knickers and a handful of skirts with him. “The store doesn’t allow people to try on underwear so I brought a few skirts and blouses too so we can probably get away with it,” he said quietly. We? What did he mean by “we can probably get away with it”? It didn’t matter because I couldn’t wait to try on some undies that were going to be my own and not soiled seconds.
Philip then proceeded to a door just beside the public changing rooms. An ordinary door which could have led to an office or a stairwell. “This is our fitting room for preferred customers,” he said. I walked in. It was the size of my bedroom and filled with mirrors from floor to ceiling. Click! He had closed the door latch behind him. Shit, that had never happened before. My natural instinct was to get out but it soon dawned on me that this would be overreacting and after all it was a pretty exciting situation.
I was in a private changing room in a big shopping mall with a cute gay Asian guy who was carrying a plethora of ladies’ clothes for me to try on. It was only 11 am, my wife was at work and wouldn’t have any inkling and now that I was here I figured I might as well enjoy the ride.
Philip lay the underwear down on a bench and hung up the rest of the clothes on hooks by the door. “First things first,” he said. “I still don’t know your name.” I hadn’t foreseen this and was completely taken aback. I blurted out my real name. “Jamie,” I replied. He smiled, “Nice name, could be either a girl or a boy’s name. Maybe from now on I should call you something else. How about Samantha? It’s nice and girly and I think that’s what you’re aiming for……...isn’t it?”
Coyly, I confessed it was. He smiled that smile again. It was devious but beautiful at the same time. If Philip had been a girl, with that fit body and tight ass, I would have been flirting with him in a second. But now the roles were reversed. He was a boy who liked other boys and I was, in his eyes, a boy who had just taken on the feminine name of Samantha. I liked the name and was beginning to relish my present circumstances. “So, you like white. Well I found a slinky white blouse you could try. Wanna try it on……for me?” I soon understood that I was his model for the morning and it really started to get me in the mood.
It took no more urging for me to start unbuttoning my shirt. I looked my lovely little Asian boy in the eyes and tried to look as seductive as possible. Once I had dropped it to the floor as casually as I could he took the pristine white blouse and walked up behind me like a tailor would do. Slipping my arms down the sleeves he positioned it over my shoulders and began to button it up from behind. I felt helpless and nervous although the blood rushing into my dick might have belied that. Philip finished doing up the buttons and lay his hands on my chest. He ran them lightly over my nipples a couple of times before running them down my sides and patting me on the arse saying, “Turn around and let’s have a look at you.”
I did as I was told. “Oh Samantha, that is so figure-hugging, so sexy.” And then he noticed the bulge. "
Perhaps it’s time we tried on some of these panties. Which ones first?”
I let him choose. After all it seemed like I was modelling for him. As he began to choose the style I undid my belt and started lowering my zip. At this sound Philip refocused his attention on me. Once I saw he was paying attention I slowly slid my legs out of the jeans. He literally gasped at my sheer white pantyhose and hard cock trying to get through my soiled white panties.
It was my turn to check out his interest. While his eyes were glued to the bottom half of my body I took a long lingering look at his crotch. It was bulging. What was inside couldn’t possibly belong to a boy his size. It was huge and no denying it.
“Do you like what you see Philip,” I asked.
“Hell yea”, he spluttered.
That was enough for me. Hooking my thumbs into the waist of the pantyhose I deftly lowered it down and kicked it off my feet while Philip looked on with eager anticipation.
As if coming out of a trance he raised his eyes to mine and slowly took the few steps over to me. He raised one hand to my cheek, lifted himself up slightly and placed his lips gently on mine. It was subtle and sensual. Instinctively I closed my eyes and returned the gesture as if I was kissing a woman. I could have been on a desert island, not in a mall dressing room but at this point it really didn’t matter. Philip slowly drew his lips away and looked at me differently. He took a step back and looked me in the eyes.
“You’ve never been with another boy before, have you?”
“No”, I replied.
“So I’m your first. Did you like it?”
All I could do was nod. Things had changed. That kiss had done it. Standing there in a beautiful blouse and a pair of panties with a young handsome boy kissing me had changed everything. I was becoming Samantha and both of us knew it.
All of a sudden my cosmetics salesman was no longer so smug. He took both of my hands in his, drew his body closer and kissed me with a passion I hadn’t felt since first kissing my future wife. It was electric. A kiss can make you do anything and this boy had that gift. Our hands broke free and we began to caress each other’s necks and shoulders. Our groins met and instead of feeling the usual hollow groove I was met by a rock hard mound. Because he was shorter than me his downturned cock was lower than mine and it fit snugly into my balls. To that point in my life I couldn’t remember ever having been so aroused. I forgot where I was and embraced this moment like I had never done before. I should have been feeling vulnerable - half-naked, dressed as a sissy boy in a semi-public place - but I wasn’t.
Philip was still on duty but I suspect he may have forgotten about that. He seemed to be in as much of a trance as me. Our kissing continued with great passion and his hands began to wander. He went from my shoulders to my sides and came to settle on my firm ass. He grasped my buttocks and pulled me tighter to him as his tongue swirled its way around mine. Both hands worked their way down the waistband of Sandy’s panties and excavated the cloth from my ass crack. Having another man’s hands inside my underwear was exhilarating. I no longer cared if we were caught, I was living something most married men never do.
As Philip disengaged his mouth from mine his lips began their slow descent to my neck while his hand, which had been placed firmly on my buttock, went in search of my anus. Within seconds I was enjoying the sensation of a finger circling my hole then finding its way to the place no-one else had ever touched. I couldn’t believe I had lived this long without knowing how much pleasure my ass could give me. He began to gently glide it over my tight spot and then placed the palm of his free hand over my groin. I nearly jumped with pleasure. There was no amateur groping or fumbling, it was an experienced hand that was exploring my cock and balls which were ready to burst out of my panties.
Philip moved away from me a little and started tenderly massaging my thighs. He couldn’t take his eyes off my bursting panties. Slowly he lowered himself down and knelt in front of me, his head at precisely at the same height as my cock. I knew what was going to happen next but I wanted to see it for myself. Looking up briefly to give me a quick naughty glance Philip inserted his fingers into the waistband of my of my knickers and expertly lowered them to just under my ball sack. Before my extremely erect cock could spring out he took hold of the shaft and let it find its natural position. His touch made me shiver with excitement and expectation.
With one hand he cupped my hairless balls as the other very lightly stroked my long, hard pulsating penis. He knew what he was doing and at this point I would let him do to me whatever he wanted. As I luxuriated in Philip’s touch my cock grew suddenly warm and wet, as if a tight pussy had enveloped it. Looking down I saw that Philip had pulled my dick towards him and had taken all of me into his mouth and was caressing me with his moist tongue and lips. Nobody had ever sucked me off so expertly before. The little slurping noises, and his reflections in the multiple mirrors, were only adding to the pleasure of seeing him on his knees with my cock in his mouth.
It didn’t take long for my balls to start stirring as rushes of ecstasy coursed through my rigid body. He could sense it and moved the tempo up a notch. At this point I watched as he moistened a finger and moved it between my legs to my ass. With consummate ease he parted my buttocks and found my anus first time. While his head bobbed up and down below me I felt him gradually work the finger into my anus. I had to adjust my stance to let him in but when I did the sensation was overwhelming. My two most erogenous zones were being catered for in harmony and I could take it no longer. My writhing stopped as I felt the oncoming orgasm rise through my body. Philip could sense it too and stopped the cock action, leaving his lips at the base of my penis. His finger though started to fuck me harder as it slid frenetically in and out of my ass.
Suddenly I went rigid, Philip violently rammed his finger further up my ass, and I exploded into his throat what seemed like and endless stream of cum. My whole body shuddered with the power of my orgasm. It took a few seconds but as it relaxed I heard him gulp down my sperm. He slowly extracted his finger from my ass and began to clean off any remnant of white fluid from my dick. Then, taking the invading finger, he suggestively put it in his mouth and proceeded to give it a good clean with his tongue. It was so erotic that my cock started to twitch again.
“Oh no you don’t,” he said, addressing my dick, “we don’t have time for any more fun.”
On that note he pulled up my panties, noticing Sandy’s pee and juices stain, not to mention my own wetness.
“These are your girlfriend’s?”
“My wife’s!” I replied.
“Naughty girl aren’t you Samantha,” he added. “There’s more to you than meets the eye. Did you enjoy your little…..session?”
“I can’t begin to describe it, I never thought I could reach such a level of horniness. Thank you.”
He leaned in and kissed me full on the lips, slipping his tongue into my mouth to give me a taste of myself.
“No, thank you,” he said, “you’ve brightened up my day and given me something to look forward to in the future. Only if you want to, that is.” He looked imploringly. I smiled coyly, raising an eyebrow but committed to nothing.
Philip took out a store card, scribbled his mobile number down and said, “I really hope you’ll use it.”
At that point it dawned on him that we had been in the dressing room far to long. All I had tried on was a blouse! What I got in return though was well worth the effort. I told him to put the blouse, a short red skirt and a handful of panties into a bag with the cosmetics and that I would be down soon to pay for them. God knows I didn’t want anyone seeing me at the cash desk with a pile of women’s clothes.
It was hard not to leave the dressing room without looking guilty. When I walked into the mall I felt nervous for wearing my wife’s underwear and now I was feeling guilty because I had just been blown and finger fucked by a guy I didn’t know in some shopping mall. With these thoughts in my head as I made my way to the cash desk I couldn’t help but smile. Philip saw this, gave me that knowing smile and then returned to professional mode.
“There you go sir, all your items are in here.” He even gave me a store discount!
Preparing to leave, his telephone number planted safely in my wallet, he whispered, “It’s my day off tomorrow. If you want I can help you with the make-up. You could model your new stuff too if you want.”
My cock started to stiffen again so I smiled, turned around and walked out the door.
Standard procedure when things get a bit bumpy is that you fix them. That’s the decent way and I adhered to it avidly during the first few years with Sandy, my pretty and rather sexy wife. We got hitched when I was 32. Four years my junior I had initially become mesmerized by her at an informal dinner party my various friends and I used to give once a fortnight. A tall, slim brunette with beautiful long legs she tantalized me for months with her short skirts and body-fitting blouses which showed off her tidy ass and small but firm breasts. It took some time and numerous dinner parties before I ever had the chance to ask her out. When I did, things just clicked.
We didn’t move in with each other for over a year. When we did, it was tough since I had always been known as, and felt like, the eternal bachelor. These final 12 months living on my own allowed me to stray on a few occasions with other women but while there was satisfaction, it singularly proved short-lived. All of these dalliances were with women who looked just like Sandy with similar figures and similar looks. None could match up though. We eventually tied the knot.
I won’t hide the fact that the initial period of co-habiting was difficult. It was excruciatingly awful at times but making up seemed to make things better. It seemed to make us stronger. It was at these moments when we really discovered each other sexually. It was as if we had been through such trauma that we were permitted to let ourselves go and to explore each other without inhibition. Those times were great but there are fewer of them now. I can’t and don’t blame her. You see, I found a new outlet for my frustrations or, rather, let’s say, I discovered a new outlet for dealing with matters which allows me to think of something aside from domestic issues.
Sandy is a secretary with a secure job and I’m a would-be journalist who’s had little success. Still waiting vainly for the big break I suppose. Anyway while she’s at her 9 to 5 job I find myself roaming around the house finding any excuse not to sit down at my desk. So I do the washing up, the tidying, vacuuming and the laundry, just like a house husband. I hated these chores. It wasn’t until I was doing the washing one day that my life changed. Sandy always insisted that I separate the whites from the colours so this particular day as I was making two piles I noticed that the whites pile consisted mainly of her knickers, bras and those sexy leggings that she often wore. What made me pay attention to this I can’t say but it certainly got my attention.
I picked up a pair of her simple white panties, turned them inside out and looked properly for the first time at the crotch stain. Where once it had been moist it had now hardened. I lifted it to my nose and breathed in. It was magical. Sweet yet not. I couldn’t put my finger on it but one thing was sure, it stirred something in my boxers. Something told me I was bordering on being a pervert but, ignoring that, I kept going.
What would it be like to put the panties on? I had taken the first step, why stop now. The laundry has no windows so I was safe. Sandy was at work. Who’s going to walk in? Feeling like a deviant I dropped my jeans and boxers to the floor and slipped the simple white panties on. It took a minute to adjust myself to the new fit but I liked the feel. It’s hard to describe precisely what I felt but it was liberating. Compared to my own underwear it was light, comfortable and, above all, sexy. I looked down at myself and saw a pronounced defined bulge which showed off the contours of my hardening dick. Unlike my own baggy boxers, these panties kept my cock pointing downwards with no room to move. It was pushing the crotch away from my body so I spread my legs and pushed it back, along with my balls, between my thighs before closing the gap again. Jesus, it looks like I have a pussy, I thought to myself and that sent me over the edge.
Such a sensation was new to me. I felt sexy, not in a butch way, but in a gentle, feminine and soft way. It felt so good. I ran my hands over the front of the panties and imagined I was touching myself as a woman. I closed my eyes and reached under my shirt to fondle my nipples as the other reached around to feel my ass. In a matter of seconds I was standing in only a pair of my wife’s underwear pulling out a bra, blouse and a pair of those sheer white leggings from the pile.
I took my time getting dressed, wanting to savour every minute but still eager to look at myself in the mirror. Apart from the bra everything felt so comfortable and warm against my skin. I was in such a state of arousal that I ran from the laundry to the bedroom. Closing the curtains I turned on the light and admired the reflection in the mirror. I looked hot and took pleasure in the prettiness of the vision before me. Nothing in my life had prepared me for this moment. The endless possibilities rushed into my head but I quickly realised there was only one thing I really wanted.
Over the next few days I repeated my actions but improved on them each time. I started by trimming my pubes so nothing would stick out the side of my panties and even used my wife’s hair removal cream to take care of the hair from my balls to my anus. By the time I was finished this area was silky smooth and very sensitive to the touch. The enjoyment of looking girly was turning me on so much that I thought about using make-up but was sure that if I used Sandy’s she would notice.
So for the first time in my life I left the house wearing soiled panties and a pair of my wife’s pantyhose, covered up by my habitual jeans. It felt so taboo and unless I got knocked over by a bus, it would be just me who knew my dirty little secret. Even though I was a bit scared venturing out of my comfort zone, the feeling was delicious.
In order to avoid meeting anyone I knew on my clandestine shopping trip I took the safe option and decided to go a bit further afield to a mall about 30 miles away. There was less of a chance of being spotted. All the way there I was getting more and more excited but also more and more nervous. I wasn’t sure if I could go through with it. What if I get caught? How would I ever explain it to my wife? I could never expect her to understand or even accept what I was doing. And frankly I would never be able to look her in the eye again.
As I was mulling these thoughts over in my head I suddenly found myself in the cosmetics department. I also realised that my knickers had bunched at the back and were now stuck in my crack. It felt so hot and was also a good reminder of why I was here. The problem though with these places is that you can’t browse without being accosted by a, more-often-than-not, salesgirl. Getting this far was one thing but having to tell somebody what I wanted was yet another, and all the while pretend it most certainly wasn’t for me! To my utter surprise the first person to come up to me was a small Asian guy of about 20 with a walk that was more suited to a catwalk. His hips swung as he approached me and while he began to smile at his potential new customer I noticed he sneaked a furtive glance at my groin. I have to admit I was a little turned on by this; it wasn’t every day that another man gave me that kind of attention.
Damn it what do I do? How do I play this? Not one thing had I thought through. Here I was trying to advance my sissy perversion and I was faced with one of those weird situations that life throws your way. “Hi”, he said. “Hey. Em, I’m looking for some simple make-up…..for a play I’m in……Pygmalion”, I added. He looked at me with a smile. “Sure”, he replied knowingly, “I can help you there. You’ve come to the right place. Philip’s my name and I can assist you with whatever you need.”
He played the game like a pro but by the time he had finished selling me cosmetics I felt that making myself up might be more time-consuming than my wicked desires could bear. “Which part in the play do you have?” I couldn’t remember Eliza Doolittle’s name so I had to improvise. “Em, just an extra…..one of the promiscuous street types”, I replied. “It’s an amateur dramatic society so we have to provide our own stuff.” I added for no reason at all, “I even have to get my own dress.”
“Well, that sounds like fun,” he said. “You’ll need to feel comfortable with all that on. Do you need any underwear for the part?” he asked without missing a beat. “As a personal shopper I can bring you anywhere in the store.” He was complicit, I knew, but I still had doubts. Hell, I’d gone this far already. “What a good idea, why not.” With an about turn he commanded, “Follow me.”
I did as I was told as he led me up two floors. It was hard to take my eyes of his skinny little butt. He moved like a woman in men’s clothing and there was no doubt at all about his sexuality. It was hard to admit it to myself but I found him cute. His knowing looks, his understanding of my needs and his willingness to please were all a big turn-on. Not to mention that he was about to confidently sell women’s underwear to another man. I was a novice in the presence of one who truly wasn’t.
When we arrived on the second floor he asked me out of the blue if I knew what kind of panties I liked. A bit too quickly I told him briefs and boyshorts, thinking of my wife’s which I had already sampled. Nothing too slutty. And white. He didn’t need to ask my size. Firstly I had no idea of women’s sizes and secondly he had already sized me up enough to already know. I was told to wait over by the changing rooms and he would be back in just a few minutes.
Doing as I was told I couldn’t help but take in the selection of clothing along my short trip. Men don’t have that much to choose from, I thought. Lucky girls, I thought to myself. It wasn’t hard to see how they could begin to seduce a man. My mind began to wander but was quickly brought back to the present by the sight of Philip with an armful of clothes. He must have had a dozen pairs of knickers and a handful of skirts with him. “The store doesn’t allow people to try on underwear so I brought a few skirts and blouses too so we can probably get away with it,” he said quietly. We? What did he mean by “we can probably get away with it”? It didn’t matter because I couldn’t wait to try on some undies that were going to be my own and not soiled seconds.
Philip then proceeded to a door just beside the public changing rooms. An ordinary door which could have led to an office or a stairwell. “This is our fitting room for preferred customers,” he said. I walked in. It was the size of my bedroom and filled with mirrors from floor to ceiling. Click! He had closed the door latch behind him. Shit, that had never happened before. My natural instinct was to get out but it soon dawned on me that this would be overreacting and after all it was a pretty exciting situation.
I was in a private changing room in a big shopping mall with a cute gay Asian guy who was carrying a plethora of ladies’ clothes for me to try on. It was only 11 am, my wife was at work and wouldn’t have any inkling and now that I was here I figured I might as well enjoy the ride.
Philip lay the underwear down on a bench and hung up the rest of the clothes on hooks by the door. “First things first,” he said. “I still don’t know your name.” I hadn’t foreseen this and was completely taken aback. I blurted out my real name. “Jamie,” I replied. He smiled, “Nice name, could be either a girl or a boy’s name. Maybe from now on I should call you something else. How about Samantha? It’s nice and girly and I think that’s what you’re aiming for……...isn’t it?”
Coyly, I confessed it was. He smiled that smile again. It was devious but beautiful at the same time. If Philip had been a girl, with that fit body and tight ass, I would have been flirting with him in a second. But now the roles were reversed. He was a boy who liked other boys and I was, in his eyes, a boy who had just taken on the feminine name of Samantha. I liked the name and was beginning to relish my present circumstances. “So, you like white. Well I found a slinky white blouse you could try. Wanna try it on……for me?” I soon understood that I was his model for the morning and it really started to get me in the mood.
It took no more urging for me to start unbuttoning my shirt. I looked my lovely little Asian boy in the eyes and tried to look as seductive as possible. Once I had dropped it to the floor as casually as I could he took the pristine white blouse and walked up behind me like a tailor would do. Slipping my arms down the sleeves he positioned it over my shoulders and began to button it up from behind. I felt helpless and nervous although the blood rushing into my dick might have belied that. Philip finished doing up the buttons and lay his hands on my chest. He ran them lightly over my nipples a couple of times before running them down my sides and patting me on the arse saying, “Turn around and let’s have a look at you.”
I did as I was told. “Oh Samantha, that is so figure-hugging, so sexy.” And then he noticed the bulge. "
Perhaps it’s time we tried on some of these panties. Which ones first?”
I let him choose. After all it seemed like I was modelling for him. As he began to choose the style I undid my belt and started lowering my zip. At this sound Philip refocused his attention on me. Once I saw he was paying attention I slowly slid my legs out of the jeans. He literally gasped at my sheer white pantyhose and hard cock trying to get through my soiled white panties.
It was my turn to check out his interest. While his eyes were glued to the bottom half of my body I took a long lingering look at his crotch. It was bulging. What was inside couldn’t possibly belong to a boy his size. It was huge and no denying it.
“Do you like what you see Philip,” I asked.
“Hell yea”, he spluttered.
That was enough for me. Hooking my thumbs into the waist of the pantyhose I deftly lowered it down and kicked it off my feet while Philip looked on with eager anticipation.
As if coming out of a trance he raised his eyes to mine and slowly took the few steps over to me. He raised one hand to my cheek, lifted himself up slightly and placed his lips gently on mine. It was subtle and sensual. Instinctively I closed my eyes and returned the gesture as if I was kissing a woman. I could have been on a desert island, not in a mall dressing room but at this point it really didn’t matter. Philip slowly drew his lips away and looked at me differently. He took a step back and looked me in the eyes.
“You’ve never been with another boy before, have you?”
“No”, I replied.
“So I’m your first. Did you like it?”
All I could do was nod. Things had changed. That kiss had done it. Standing there in a beautiful blouse and a pair of panties with a young handsome boy kissing me had changed everything. I was becoming Samantha and both of us knew it.
All of a sudden my cosmetics salesman was no longer so smug. He took both of my hands in his, drew his body closer and kissed me with a passion I hadn’t felt since first kissing my future wife. It was electric. A kiss can make you do anything and this boy had that gift. Our hands broke free and we began to caress each other’s necks and shoulders. Our groins met and instead of feeling the usual hollow groove I was met by a rock hard mound. Because he was shorter than me his downturned cock was lower than mine and it fit snugly into my balls. To that point in my life I couldn’t remember ever having been so aroused. I forgot where I was and embraced this moment like I had never done before. I should have been feeling vulnerable - half-naked, dressed as a sissy boy in a semi-public place - but I wasn’t.
Philip was still on duty but I suspect he may have forgotten about that. He seemed to be in as much of a trance as me. Our kissing continued with great passion and his hands began to wander. He went from my shoulders to my sides and came to settle on my firm ass. He grasped my buttocks and pulled me tighter to him as his tongue swirled its way around mine. Both hands worked their way down the waistband of Sandy’s panties and excavated the cloth from my ass crack. Having another man’s hands inside my underwear was exhilarating. I no longer cared if we were caught, I was living something most married men never do.
As Philip disengaged his mouth from mine his lips began their slow descent to my neck while his hand, which had been placed firmly on my buttock, went in search of my anus. Within seconds I was enjoying the sensation of a finger circling my hole then finding its way to the place no-one else had ever touched. I couldn’t believe I had lived this long without knowing how much pleasure my ass could give me. He began to gently glide it over my tight spot and then placed the palm of his free hand over my groin. I nearly jumped with pleasure. There was no amateur groping or fumbling, it was an experienced hand that was exploring my cock and balls which were ready to burst out of my panties.
Philip moved away from me a little and started tenderly massaging my thighs. He couldn’t take his eyes off my bursting panties. Slowly he lowered himself down and knelt in front of me, his head at precisely at the same height as my cock. I knew what was going to happen next but I wanted to see it for myself. Looking up briefly to give me a quick naughty glance Philip inserted his fingers into the waistband of my of my knickers and expertly lowered them to just under my ball sack. Before my extremely erect cock could spring out he took hold of the shaft and let it find its natural position. His touch made me shiver with excitement and expectation.
With one hand he cupped my hairless balls as the other very lightly stroked my long, hard pulsating penis. He knew what he was doing and at this point I would let him do to me whatever he wanted. As I luxuriated in Philip’s touch my cock grew suddenly warm and wet, as if a tight pussy had enveloped it. Looking down I saw that Philip had pulled my dick towards him and had taken all of me into his mouth and was caressing me with his moist tongue and lips. Nobody had ever sucked me off so expertly before. The little slurping noises, and his reflections in the multiple mirrors, were only adding to the pleasure of seeing him on his knees with my cock in his mouth.
It didn’t take long for my balls to start stirring as rushes of ecstasy coursed through my rigid body. He could sense it and moved the tempo up a notch. At this point I watched as he moistened a finger and moved it between my legs to my ass. With consummate ease he parted my buttocks and found my anus first time. While his head bobbed up and down below me I felt him gradually work the finger into my anus. I had to adjust my stance to let him in but when I did the sensation was overwhelming. My two most erogenous zones were being catered for in harmony and I could take it no longer. My writhing stopped as I felt the oncoming orgasm rise through my body. Philip could sense it too and stopped the cock action, leaving his lips at the base of my penis. His finger though started to fuck me harder as it slid frenetically in and out of my ass.
Suddenly I went rigid, Philip violently rammed his finger further up my ass, and I exploded into his throat what seemed like and endless stream of cum. My whole body shuddered with the power of my orgasm. It took a few seconds but as it relaxed I heard him gulp down my sperm. He slowly extracted his finger from my ass and began to clean off any remnant of white fluid from my dick. Then, taking the invading finger, he suggestively put it in his mouth and proceeded to give it a good clean with his tongue. It was so erotic that my cock started to twitch again.
“Oh no you don’t,” he said, addressing my dick, “we don’t have time for any more fun.”
On that note he pulled up my panties, noticing Sandy’s pee and juices stain, not to mention my own wetness.
“These are your girlfriend’s?”
“My wife’s!” I replied.
“Naughty girl aren’t you Samantha,” he added. “There’s more to you than meets the eye. Did you enjoy your little…..session?”
“I can’t begin to describe it, I never thought I could reach such a level of horniness. Thank you.”
He leaned in and kissed me full on the lips, slipping his tongue into my mouth to give me a taste of myself.
“No, thank you,” he said, “you’ve brightened up my day and given me something to look forward to in the future. Only if you want to, that is.” He looked imploringly. I smiled coyly, raising an eyebrow but committed to nothing.
Philip took out a store card, scribbled his mobile number down and said, “I really hope you’ll use it.”
At that point it dawned on him that we had been in the dressing room far to long. All I had tried on was a blouse! What I got in return though was well worth the effort. I told him to put the blouse, a short red skirt and a handful of panties into a bag with the cosmetics and that I would be down soon to pay for them. God knows I didn’t want anyone seeing me at the cash desk with a pile of women’s clothes.
It was hard not to leave the dressing room without looking guilty. When I walked into the mall I felt nervous for wearing my wife’s underwear and now I was feeling guilty because I had just been blown and finger fucked by a guy I didn’t know in some shopping mall. With these thoughts in my head as I made my way to the cash desk I couldn’t help but smile. Philip saw this, gave me that knowing smile and then returned to professional mode.
“There you go sir, all your items are in here.” He even gave me a store discount!
Preparing to leave, his telephone number planted safely in my wallet, he whispered, “It’s my day off tomorrow. If you want I can help you with the make-up. You could model your new stuff too if you want.”
My cock started to stiffen again so I smiled, turned around and walked out the door.
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