Cross Dressing
05 Jan 2018


Previous story in series: When your Girlfriend discovers she is dating a cross dresser.

We have all had those experiences of meeting someone on-line and chatting and things really get hot and exciting and then the huge let down when the person leaves you hanging with a hard-on or even worse when the time comes to meet they don’t show.

Well this story is one with a happy ending.

I met Paul (not his real name), on line and we chatted for ages. He was from a town about an hour away so on-line chatting was really our only safe way of communicating. When he found out I was into cross-dressing, our on-line chatting became really sexy and exciting for both of us. We chatted whenever we could and we both starting to explore our fantasies with each other, which in turn led to many an orgasm on both sides. I wear panties to work just about every day and whenever I could, I would also cam for Paul. These sessions were especially exciting as I would wear the panties of Paul’s choice and then go about doing what he would like to see which always ended with an explosion on my side. More often than not it would be in my panties and as I would later discover this was all part of what turned him on the most.

After nearly a year of chatting and exploring our fantasies on-line, we eventually agreed to meet. We arranged to meet at a hotel midway between us for a drink and a chat. I still remember being so nervous when the day arrived. I had met other men and women over the years but this time it just seemed different as it had taken so long and we had chatted about so much. When I arrived at the hotel he was already there seated out front with a drink and watching the ocean. I walked up and as soon as he saw me he stood up, smiled and took my hand. There was no one else within earshot and the first words out of his mouth were, “Hi Samantha, it is an absolute pleasure darling.” Just seeing him, feeling his hand holding mine and calling me Samantha, had me almost explode in my panties right there and then. He must have seen the effect as he smiled and invited me to quickly sit before my legs gave way.

We sat and chatted over a couple of drinks and it was obvious from our hushed conversations that we were both really enjoying the meeting. By now I was exceptionally wet in my panties. Paul wanted to see what I was wearing and we agreed to meet in the toilet. I left before him and a couple of minutes later he arrived. He coughed to let me know it was him. I opened the cubicle door and let him in and then locked it again. He moved up against me as I leaned against the wall. With him whispering in my ear how much he had been dreaming about this moment, I could feel his hand between my legs. Finding my hardness, he gently rubbed it through my trousers as his lips found mine and then his tongue was probing and soon our tongues were tasting each other. We kissed passionately, my breath catching as his hand was now unbuckling my belt. Then my trousers were falling to the floor and he stopped, stood back and stared at me in all my glory. Standing there in my panties, stockings and suspenders.

Then he is leaning in again, telling me that I look so damn sexy. Kissing me again as his hand finds it way between my legs again and he began gently rubbing my hardness through the silky panty material. By now I was oozing precum in my panties and he could feel how wet he was making me. I wanted to touch him but he would not let me. He told me to just go with the moment. I was so excited and soon without warning I was suddenly exploding right there and then in my panties. My finger nails digging into Paul’s shoulders and back as I lost control and succumbed to the pleasures of release. Paul continued to gently stroke me in my panties and the feeling was so intense that it felt like I was cumming for ages. We stood there kissing long after the orgasm was finished and Paul just continued to spread my cum all over my panties. Eventually he lifted his hand and offered it to me. He whispered in my ear that I should taste. I licked his fingers ever so gently to start with and then sucked each one wanting to get every drop but the most amazing thing was that I found it so erotic. Then he is telling me how sexy and exciting this was and I have just made his day. I wanted to touch him so desperately but he would not let me. He then said he was going to have to go but that he wanted to meet at a hotel for an extended private session. Driving out of there that day with cum soaked panties left me looking so forward to our next meeting.

We stayed in touch and enjoyed a few more sexy cyber and cam sessions and then about 5 weeks after the 1st encounter he told me he was brining his car to the city for a service and would be in town all day while he waited for it. We arranged to meet at a hotel for the day. This time I was there before he got there and was dressed as requested. Black satin and lace corset, silky panties with lace front, thigh high stockings, heels, full make-up, painted nails and wig. A knock on the door and I am opening it to find a smiling lust looking Paul. No sooner is the door closed and he is kissing me passionately. He stops long enough to take a step back, look me up and down, he takes my hand and has me twirl to give him the 360º view and then leads me to couch in the lounge. He sits and then has me sit on his lap. He tells me how much he has been dreaming of this and then our lips meet again. This time he is so gentle and slow. Kissing me so softly yet so erotically, then moving to my neck and gently kissing up to my ear and then I can feel his tongue teasing my ear lobe, then a little nibble. God by now my hormones are raging.

Then back to kissing and now he can feel and hear the effects he is having on me. I am battling to prevent the little moans of pleasure from escaping. We both love kissing, my one arm around his neck, my one hand on his face as I can’t get enough of him. Then his hand is exploring my body, feeling me through my satin corset. My nipples are erect and he slips his hand inside to discover them and to gently tease them with the tips of his fingers. First one and then the other. My body is responding to every little touch now. Then his hand is exploring further south now, finally arriving at my silky and lace panties. My hardness is tucked between my legs and soon his hand discovers the wet patch of panty covering my hard cock. I breathe a deep moan and like before he gently proceeds to touch, tease and rub my harness through my panties. I moan to him that I so want to feel him. I can feel his hardness pressing into my panty cover ass. He just tells me to be patient.

I lost track of all sense of time as we sat there kissing while Paul went about touching, teasing and rubbing and each time I thought I was going to explode he would suddenly stop touching me and just kiss me. I kept telling him he was driving me crazy and he would just say, “I know. I will let you cum when the time is right” He would run his hands up and down my stockings and then always come back to my now soaked panties. He had me oozing precum in them and he kept telling me how wet I was getting and how much he liked it. I am not sure how long it took but eventually I reached the point of no return. My back arched and I felt his hand really apply pressure between my legs as he pressed down on my hard throbbing cock and suddenly I was exploding in my panties. He kept his hand in place and continued to apply pressure with a little stoking movement up and down my hard cock in my panties as I continued to fill them. I was so caught up in the throes of pleasure and could not prevent the animal sounds escaping me. Like before he did not stop and once my body had finally stopped with the shaking he very gently continued to stroke my panties and tell me how amazing that orgasm was to watch and to experience.

I lay off to one side on the couch trying to recover but the sensations just kept coming. My legs were over his legs, slightly parted with his hand still gently rubbing all the cum through my panties. I could feel I was still pretty hard. He was looking at me and smiling and all I could think of was his hard cock. I told him I so needed to feel and touch him but still I was told to wait. Then he lifted my legs, extracted himself from beneath them, knelt, had me lift my bum and then he proceeded to remove my panties. He inspected them and then revealed to me just how much cum I had just produced. He then offered the panties to my lips and had me taste my juices. I was so turned on that when he asked me to lick and suck them I was almost like a little slut on heat who could not get enough of my own cum. I sucked those panties like they contained the last drop of cum on this earth. He sat there with the biggest smile on his face watching me.

Then he stood, walked into the bedroom and returned with my little vibrator and some lube. God I could not believe this. This time he knelt on the couch and spread my knees. His lips were on my stockings and worked his way up my legs to my thighs and then eventually to my almost hard cock. Then he was licking, teasing, gently stroking and then I was in his mouth. Oh my god I was in heaven. Then I felt his finger probing my tight hole. I could feel the lubricant being applied and then his finger finding its way inside. He started to gently finger my tight hole while his lips, tongue and mouth worked my throbbing cock. I was back in that space of pleasure that just takes hold of you. Then I heard the vibrator and felt it probing and then it was inside me. He worked it ever so slowly in and out making sure that the lube made it easy. Then he was slowly fucking my tight hole with it as he really worked my cock with his mouth. I could feel the orgasm building, almost as if it was coming from my toes and working its way up. I don’t think I lasted 10 minutes and I was cumming for a 2nd time, back arched again but this time the orgasm was from deep within me and not just cum oozing from my cock. I could feel my muscles clinching around the vibrator, not wanting to let go as my whole body shook with spasms which seemed to last forever.

I just lay there, totally spent, not wanting the moment to end. Paul got up, fetched me some water and then sat there with me as I recovered. He proceeded to tell me that we had just lived out his fantasy. He had always wanted to do that and to watch as the person lost total control for him. I told him that I needed to feel him and to satisfy him and he informed me that I had just done that by allowing him to have his way with me. I almost begged him to let me touch him and he told me I would soon. When Paul was happy that I was not going to pass out on him, he finally stood in front of me. He proceeded to tell me that he hoped that I would not be disappointed but that he was rather embarrassed as his cock was not very big. I have never been one to judge a guy by his cock size and told him so. I was also quick to point out that I liked small to average size cocks and when he eventually unzipped and revealed his cock I could see it was quite small. However it was beautiful. Cut and with such a beautiful head. I looked up at Paul and I think he could see the desire in my eyes.

With him standing there, I knelt in front of him, pulled his pants and underwear all the way down and helped him out of them. I then proceeded to slowly take his cock, all 4½ inches which was now very hard, in my mouth. I slowly licked, sucked and teased it hearing his moans of pleasure. He allowed me to alternate from teasing just the head and then taking all of him into my mouth for a couple of minutes. I was so hungry for his cock by now and had other ideas of wanting to feel him inside another hole of mine. It was the perfect size for my tight hole.

With his hands on my head, holding my hair, he started to slowly thrust his cock into my mouth. I could almost feel his wanting to fuck my mouth. So I just relaxed and let him guide me. My mouth open, tongue flicking and teasing when I could, I slipped my hand up and took hold of his balls and gently squeezed. This brought another moan from him and his grip on my hair tightened. His thrusting movements got a little more intense and I could feel his balls start to tighten. Then he was saying he wants to cum in my mouth and suddenly without warning he is cumming. At first I was not sure and almost pulled away but then suddenly my hands were on his arse and I was pulling him into my mouth. I was so turned on too that I just wanted to feel and taste his man juices. He held me like that for a full minute or so as shuddered and filled my mouth. He did not cum as much as I thought he would but there was certainly enough for some of it to escape and run down my chin. When he was spent he sat down on the couch and pulled me up next to him. He leaned over and kissed me, tasting his juices, noticing the dribble down my chin, he used his finger to scoop it up and then presented it to me which I happily licked and sucked off his finger. Then he leaned in again and kissed me tasting his juices on my tongue.

We spent the next hour or so just chatting, recovering and enjoying each other’s company. I discovered that he was so nervous about me not liking his small cock and the fact that he liked to be in control. He was worried that I would not allow him to do what he had done to me. I let him know that I loved the way he made me cum, and the way he did it, and that I always liked a man that knew what he wanted. I told him that what he had done to me was so damn exciting and hoped to be able to experience it again.

We parted company that day and we did meet another 3 times after that when the car needed servicing. Every time was pretty much like the first, with him having his way with me first and then allowing me to pleasure his cock. After that Paul left for another job and another city, so we have been left with only the net to keep our little sessions going. Just wanted to say thanks again for everything Paul.

Next story in series: When your Girlfriend discovers she is dating a cross dresser.


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