This is my very first story and is an episode of crossdressing that became so much more with a friend and a stranger. Some of it is based on fact, scary but true.
Friday was a half day at work for me and was a more casual day than the rest of the week and I had decided to take the opportunity to work from home. Like many other times on this occasion, nobody would know, I had no appointments, my boss was on holiday, my children were at college and my wife was at work. I had known all along my true motivation for working at home today, which was not because I had something I needed to concentrate on in peace but to partake in my secret fetish of crossdressing.
By 8.30 the house was all quiet and I was finally alone and knew I would be for many hours, so I quickly went to the garage and fetched my female clothes, which were stored there and took them up to my room in their large plastic bag. My normal clothes were off in no time and I started to pick out the items that I really wanted to wear. For underneath I chose a small white pair of panties, which were made out of a stretchy material that was almost see through, and that hugged my cock and balls tightly and a matching smooth white bra to match my panties, not that I had any breasts but I had found one almost my size with a small cup size and it made certainly me feel more feminine. Next I pulled on a pair of my black opaque tights, I had recently shaved my legs and bum, so they nylon felt good as it rubbed up my smooth legs. Trying to achieve an office girl look, I put on a blue skirt, which was too small for me really but it had an elasticated waist and was made of a stretchy material, it only came down to mid thigh and so revealed most of my legs and then it hugged my bum tightly. Although now dressing out of a normal sequence, next I slipped on some black court shoes with a two-inch heel, enough to make me feel feminine but still sensible enough to walk around in without falling over. I stopped for a while and admired myself in the mirror, my face was that of a man but I loved my body and how it looked, maybe I imagined it but I even thought that I had slightly feminine curves as my hips were wider than my waist and I had good looking legs. As I looked at my reflection, slowly my hands moved over my own body, touching myself gently and I enjoyed the sensation of feeling myself and also that of being touched and wished to myself that it was someone else who was touching me. Finally I finished the outfit off with a thin soft white short-sleeved blouse, which had the buttons undone to the point that you could just see my bra. There was no need for this as the material was so light on the blouse that the outline of my bra could be clearly seen through it anyway.
I was very pleased with the way I looked, perhaps too pleased because my heart suddenly started racing with the realisation of what I now wanted to do. For the first time ever I wanted to apply some make up to make myself look even more feminine, so I made my way into my daughters bathroom where I knew there would be a much better choice. Not really knowing what I was doing, I applied some foundation with from a container with the pad that was with it and with a bit of practice I could see my cleanly shaven skin becoming smoother and looking younger and then some blusher to bring out the shape of my cheekbones. Next I applied some eyeliner, I remembered something that I had read on the internet about how too many inexperienced crossdressers applied too much make up and so made themselves look too obvious, so I was careful not to overdo it with this. I was pleased with the outcome as I started to look and feel more feminine with every little change. A little bit of mascara was next, fortunately my youngest daughter had some that wasn’t waterproof, which was ideal as I wanted to be sure that I could get it off afterwards. I felt my body movements becoming more lady like as I progressed as I slipped further into my female persona. Next was a bit of eye shadow, a fairly subtle pink which I thought matched the blusher perfectly. One more thing was required, some good old fashioned lipstick, only I found some in a make up case that wasn’t old fashioned, it was a nice bright red and not in a stick at all, it was in a tube and applied with a pad type brush, which made it easy to get a good coverage and was easy to use to emphasise the shape of my lips, which now looked a much more delicate shape all together, after reading the tube I applied some gloss to keep it in place longer and give my lips a nice sheen.
Felling good about myself, but at the same time as nervous as hell, with my heart beating fast in my chest, I made my way back to my bedroom to have another look in the full-length mirror. I was looking good and not like me at all, but my hair was still to short and manly and I felt disappointed as this was letting me down. Then I had a eureka moment, I’m sure my eldest daughter bought a cheap wig for a fancy dress party, but didn’t wear it as she found it uncomfortable, oh god I hope she didn’t throw it away. I searched around her bedroom but I couldn’t find it, the room was a tip, it’s a wonder she could find anything at all. I looked in her wardrobe as was relieved to find it thrown on the floor in the far corner almost out of sight. I picked it up and held it up, amazingly the platinum shoulder length blonde synthetic fibres fell straight and I could see that it wouldn’t take too much work to sort out and to make presentable. Awkwardly I placed it on my head and moved it into place and then even I was astounded by the immediate transformation that took place before my eyes. The wig had been the last piece of the jigsaw, as I combed it neatly it was not me looking back out of the mirror, I had become a woman, not a bad looking one either and my cock stiffened in my girly knickers with excitement, oozing precum already.
To capture the moment I spent the next half an hour setting up my camera on a tripod and taking pictures of myself, which I immediately posted onto my flickr web site. Again my heart was beating like mad in my chest as this was the first time that I had posted pictures showing my face, although I wasn’t worried as I didn’t even think that my wife would recognise me. The responses were immediate with positive comments and mails coming in with people trying to make contact. Some of the mails were down right dirty and as I read them I got excited with the thought of what some men out there would like to do to me.
I felt intoxicated in the moment and I was forgetting where I was, which was the dining room at the front of my house, when a loud knock at the door brought me straight back to reality. A birthday present that I had ordered for my daughter from the internet was being delivered and it was early, I had only ordered it two days previously and was not expecting it yet. I got up from the dining table quickly and shot into the lounge where I wouldn’t be seen, but it was too late as I had been seen.
“Come on love don’t mess me about,” the deliveryman shouted through the letterbox, “you need to sign for this parcel and if I don’t deliver it now I’ll have to take it back to the depot and I could do with going straight home.”
Damn it, I thought to myself, he knows I’m here, I was petrified at the thought of being seen but at the same time I was a bit excited at the thought of being mistaken for a woman.
“Come on darling,” he shouted again, “give me a break.”
My mouth went dry, this was stupid, I knew I had to answer the door as the deliveryman didn’t seem to have any intention of leaving without leaving the parcel, but Jesus I was scared. There was no way that once the deliveryman got close enough that he wouldn’t realise that I was really a man, but then the chances of ever seeing this man again was so remote that it didn’t really matter. I felt sick with anticipation and I could hear my heart beating, but at the same time my cock went rock hard with excitement and as if without thinking, rational thought went out of the window, my cock took control of my body and I walked down the hall and unlocked the front door.
How I wasn’t actually sick when I opened the door I will never know as I found myself standing at an open front door for anyone in the road to see. The parcel had to be signed for so I took the pad from the deliveryman and signed my name before taking the parcel and placing it in the hall. I started to understand how some women feel as I could see this stranger undressing me with his eyes, which never left me, as he looked me up and down several times, I could sense that he was dying to say something but wasn’t sure what to. I was starting to feel much more confident now, the initial thrill of opening the door was starting to subside and I was getting desperate to keep the feeling, so when I put the package down I turned my back on the deliveryman and bent down keeping my legs straight and causing my short skirt to rise up the back of my legs to my bum. The strangers eyes never wandered from my body, I know this because I kept an eye on him all the time. Finally he had to speak.
“Fuck me! I know you’re a man, but you look fucking good.” He stated as he even stepped up the step into the doorway to get a closer look.
“Oh I’m all man,” I replied as I deliberately dwelled in my position of being fully bent over. I was really enjoying exposing myself now, so I suppose I sort of invited the attention, even so I was shocked as I felt a hand gently touch the top of my legs and a finger move between them to touch the back of my balls.
“So you are.” The stranger said.
My female persona took over as I softly squealed “Ooh!” then I stood up and looked the stranger in the eye and retorted, “You’re a bit forward aren’t you?” I felt precum now oozing from the end of my cock with excitement.
“Don’t tell me you don’t like the attention gorgeous.” The deliveryman said back to me, now only inches away from my face and looking me straight in the eye.
Who made the next move I’m not entirely sure as certain moments have become a bit of a blur, but almost instantly this total stranger was kissing me, or was I kissing him I’m not sure but anyway it didn’t matter. What I do know is that our mouths moved to each other’s and that the kiss that followed was passionate and forceful, more forceful than any I have ever received from a woman and I liked it. What’s more, I felt hands wandering all over me, this mans touch was less gentle now as I felt him hold me tightly around my body with one arm and the hand of his other arm grip my bum and then move around to my stiff cock.
I was totally intoxicated by the moment and had forgotten that I was dressed as a woman and kissing another man by my open front door, I had just placed my hand over this other mans cock, which I could feel was now rock hard, when I heard another voice at the door.
“Am I interrupting anything?” I heard my sometimes tennis partner Chris ask who was sounding very surprised at what he’d found.
“Oh shit!” I gasped, slumping my head onto the shoulder of the stranger holding me.
“Don’t worry love,” he said to me in a reassuring way and embracing more gently now, then he commanded to Chris, “get in here and close the fucking door for gods sake, before we have even more people coming in.”
We had to move to allow Chris to come in so I moved out of the deliveryman’s arms, taking him by the hand and leading him into the lounge, which was at the back of the house. Chris stepped into the house, closed the door and followed us. The deliveryman took me into his arms again, placing his hand on my thigh before moving it up to my bum and lifting my skirt up in the process.
“Kev, what are you doing?” Chris asked me.
I didn’t need to speak, as the deliveryman answered for me, “Isn’t that obvious?”
“Mind you, you do look surprisingly good,” Chris added.
“She’s fucking gorgeous,” said the stranger, “and I reckon she’s going to let us fuck her. Aren’t you?” He added now looking at me.
I suddenly realised what I had got myself into and what was about to happen and I became excited again, my cock which had previously shrivelled up in a pool of precum now stiffened again.
“Well you are aren’t you?” he asked again and I could see my heart visibly beating in my chest.
Still short of breath, I replied. “Oh yes, I’m going to let you fuck me, both of you if you want,” I said still in the strangers arms but now looking at Chris.
“Come and give the lady a kiss,” the deliveryman ordered.
Without hesitation, a man that I had known for years, moved across the room to me and took his turn in taking me in his arms and kissing me passionately and yet again I was amazed at how good this felt. I had now become a woman and so in my mind I was kissing a person of the opposite sex so where was the problem in what I was doing, so I threw myself into things completely. The deliveryman kept hold of me too as I kissed Chris, so I was being squeezed between two strong men’s bodies and I loved it. I felt the hand of the man behind me move down from my stomach to below the level of my short skirt, where it then moved its way back up inside my skirt, stroking my erect cock and then up to the waistband of my tights. I breathed in, holding in my stomach willing the next move as I felt the mans hand move inside my little knickers and wrap itself around my sticky cock.
“Well you dirty little bitch, you’ve been making a right mess inside your knickers haven’t you and now they’re all sticky.” I didn’t answer, as I was far too busy enjoying kissing my old friend, our hands were now wandering all over each other like teenagers. The deliveryman may have started to feel left out at this point as he turned me around, separating me from my new lover. “It’s time you started paying me some attention.” He told me. “Now get down and get my cock out bitch.”
Now facing the stranger, I started kissing him again to keep him sweet, while reaching down and unzipping his flies. Once open I reached in to grab his cock but I was frustrated at the access so I continued by releasing his belt and trousers, which dropped to his knees and so allowing me to slip down his pants and get both hands onto his cock. This was the first time I had ever touched another mans cock and I was amazed at how good it felt, so good that I needed more, so I sank to my knees in front of the stranger. Once on my knees I could get a closer look, it was beautiful and smooth, it was probably bigger than mine and much to my relief it looked nice and clean. Without hesitation I pulled the foreskin back and rubbed it a few times before taking the head into my mouth, yet another first for me. This man tasted good so I ate on it hungrily, so good that I wanted more, so I pulled Chris around to his side as I wanted his too. From below I looked up at my friend as I unfastened his trousers before pulling his trousers and pants down to his knees, revealing a huge erection.
“Fuck!” I said out loud, as I saw for the first time that my friend Chris was hung like a horse. “That’s a monster darling.” I told him as I looked at his cock, which had to be nine inches long and it was thick, much thicker than my own. I was envious of this huge cock but at the same time I was excited as I knew that I could have it now and I felt yet more precum leak into my pants as I nearly came there and then. I placed both of my hands around this large tool and I still didn’t manage to cover it all, then I pulled Chris’s foreskin back before taking my second ever cock into my mouth. What was happening to me, I was discovering a whole new side of me, my friends cock tasted so sweet and I couldn’t get enough of it and I knew right there that I wanted to try and take him inside me.
Before very long I could see the deliveryman getting impatient so I moved from Chris’s cock to his to keep him happy for a while. I was desperate to be filled and I wanted it to be Chris, so I quickly formulated a plan.
“Chris darling, get the baby lotion out of the bathroom and fuck me please, while I take this stud in my mouth, I want to taste his cum.”
As Chris left the room my stranger spoke, “You really are a dirty slut aren’t you, he’ll rip you apart with that monster, but like I care, just take me and drink my cum.”
As Chris returned into the room I was busy eating the deliveryman’s cock, but not put off by this he knelt down behind me, lifted my skirt and pulled down my tights. I felt him grab my panties next, but I asked him to leave them in place and just pull them to one side, I didn’t tell him why but I was enjoying my cock swimming in a sticky mass of precum held inside the fabric. Gently my new lover applied some baby lotion over my bum, which made me gasp a little as it felt so cool. Next he pressed a lubricated finger inside me, knowing that it would be best to lubricate me internally and to open me up a little. I felt a second finger enter my ass and my head started spinning as I felt yet a bit more precum leak into my pants, I had to concentrate to carry on sucking my stranger’s cock as I was enjoying what was going on behind so much, but I had to come up for air to tell my friend.
“Fuck me please Chris. Fuck me now I need it.”
I took the strangers cock back into my mouth and continued sucking, raising my right hand to pump his shaft as I sucked on his knob as I felt my pants being pulled to the side. My stranger tasted good and had almost taken my mind of Chris again until I felt the warmth of a huge head move up to my ass and press gently, moving into position and just opening me up, but only very slightly. Then I felt a pair of strong hands grab the front of my hips and with one huge push my new lover pushed forward while pulling me back against him with his hands. A shockwave of pain and ecstasy shot though my whole body making me gasp and as I did so I was launched forward taking my strangers cock right into the back of my throat. I felt my colon being stretched wonderfully and a pressure applied to my prostrate by the huge member inside me, causing a big spurt of cum in my knickers. Then as Chris pulled back and powered forward again, with each stroke that he made another spurt of cum shot out of my cock uncontrollably and now the thin material could no longer take the sheer volume of sticky liquid as it now oozed out and dripped onto the carpet below. The sight and sound of the white liquid splattering down onto the floor didn’t go un-noticed by my lovers, causing them both to laugh at me.
“Crikey you are enjoying this aren’t you?” said Chris.
“Oh yes she is the dirty bitch,” replied the deliveryman, “she can’t get enough.”
He was right, at this moment I couldn’t get enough, I had become a dirty bitch and would have taken on all comers at this point, but as it was I just concentrated on the two that I had. I worked my stranger’s cock hard with both my hand and mouth, he was rock hard and his balls were tight. I asked him to sit down so that I could rest on my elbows and still use my hands to pleasure him and obligingly he sat himself with his legs splayed to either side of me. Once he was in a more accommodating position I could hold his shaft with one hand, cup his balls with the other and still suck him, while Chris continued powering into my bum. My deliveryman seemed to enjoy this new position even more and it wasn’t long before I felt the undeniable twitching which was a sure sign that he was about to cum. The realisation that this was going to be the first cum that I have ever tasted other than my own washed over me, but I wasn’t worried, I wanted it, lots of it. My bold stranger didn’t disappoint me as I felt a jet of liquid pump into my mouth. At first it didn’t seem much, but on feeling it I gripped his cock harder and pumped it causing a bigger second stream of cum and then one after the other until my mouth was full of a delightful tasting liquid, so much nicer than mine ever tasted. I was torn as to what to do, do I swallow it all or do I keep it and savour it for longer, but in the end my mouth was so full that I had no option but to swallow some but managed to keep a large amount that I swirled around my mouth. I sucked my stranger dry and I was proud that I never let a drop leak from my lips, which was amazing considering the pounding that I was still getting in my rear.
“Bloody hell you’re good!” my deliveryman stated.
“Thank you,” I said looking up at him with a cheeky smile.
In no time after I had emptied my mouth that I heard Chris grunting, warning me that his time was near. Just as I was considering if I should take Chris out and take him into my mouth, I felt him pulsate inside me, and then the feeling of warmth deep inside me as he filled me with his seed. Dear old Chris must have needed the relief as he continued pumping into me with his huge cock, injecting what felt like gallons of semen into me. I would have to make sure that he knew that he didn’t go without relief in the future as I had found my true vocation in life, I wanted to be a crossdressing whore, giving relief to handsome needy men.
Once finished Chris pulled out and pulled my pants back into place and allowing me to finally slump onto the floor in a hot sticky mess. I pulled up my tights again as I could feel that liquid would be soon leaking from front and back and I wanted to contain it, both for my enjoyment and to protect my already cum stained lounge carpet.
“Well I have to go.” Announced the deliveryman, who then bent down to kiss me before walking out. As I lay in the foetal position on the lounge floor, enjoying the warm feeling inside me and the taste in my mouth Chris made sure that the stranger left before returning to where I lay. To my surprise Chris sat beside me, partly picking me up, taking my head and shoulders into his arms. Again I felt very feminine as I lay in the strong arms with cum leaking out of my bum and oozing out of the front of my knickers, while my new lover leaned over me kissing me tenderly.
“Oh baby that was so good,” he whispered, “you don’t have to dress in secret anymore. I will be here for you when ever you want my lovely girl.”