12 Feb 2019
When your Girlfriend discovers she is dating a cross dresser.
Being caught - The 3some - The humilliation - The happy ending
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54 minute read
Previous story in series: Crossdress Fun
Arriving back from overseas and having had the amazing experience with Lars and Anna with them helping me to truly accept my other being, Samantha, it was time to get back into life here in South Africa.
The experience of embracing my feminine side and accepting my cross-dressing was unfortunately going to have to take a back seat as I moved back in with my parents upon my return. For the next 3 months while I lived at home and found a job while finding my feet I was limited to a couple of pairs of panties that I would sleep in and then hide each morning before leaving the house.
Then, gainfully employed and able to find my own place to live I immediately ran out and bought some new lingerie. I would most days wear panties to work and then could not wait to rush home to embrace my feminine side and just be Samantha. This went on for almost a year until I met Sally. This prompted me to place all of Samantha’s lingerie in a small case with a lock on it and hide it in the top of my cupboard right at back behind some boxes. I was not going to be going to work wearing lingerie anymore, although I did on occasion take the case down on those evenings when my desires just could not be chased away.
Sally started working for the same company I was employed at and I have to admit that from the first moment I saw her I was smitten. She was tall and sexy but had something about her that just got my juices going. Every time I was in her presence I found I was bumbling idiot.
About 2 months after meeting her we ended up at a company function together and a few hours in and quite a lot of alcohol under the belt I eventually plucked up the courage to go across and chat to her. Her response to my feeble hello was, “Well, it too you long enough.”
It did not take me long to realize that here was a strong women who knew exactly what she wanted. By the end of the evening she was flirting big time and when the time came to leave she simply said, “so we are going back to your place.” I got my first taste of this sexy beast on the way home. No sooner we were on the road and she is leaning over, unzipping me and before I knew it her head was in my lap and she was giving me the most amazing blow job. I am not sure how I even managed to get us home safely.
No sooner were we through the door and we were ripping off each other’s clothes. We barely made it to the bedroom. She was gorgeous without her clothes on. Small firm breasts, slim with these gorgeous long legs. The kissing was hot and passionate, my hands roaming her body, discovering what she enjoyed as her little moans of pleasure became more intense. Then she had hold of my throbbing cock and was telling me she needed to feel me inside her. She pulled me on top of her and she guided my cock into her pussy. She was so wet and before I knew it she was pulling me all the way inside her. Her hips thrusting up to meet my hard cock.
We were so desperate for each other at this point that our thrusting was becoming almost animal like. Her moans of pleasure becoming louder, bringing me closer to the edge with each thrust. Then she is throwing me over with a strength that surprised me. Now with me on my back she climbs on top of me and takes my throbbing cock and slips it back into her. With her in control she starts to ride and grind away. Her head back, her long blonde hair in disarray, my hands finding her breasts and gently squeezing them and teasing her perky erect nipples. Then she leans forward and puts her hands on my chest and I can feel her pussy muscles tighten and I know we are about to cum.
I feel her nails dig into my chest. The moan that escapes her is so loud as she grinds herself against me. My orgasm erupts as I lift up to meet her and we are both cumming so hard. Her orgasm seems to go on forever as she continues to work my cock for some time after my eruption. Eventually she slows and then climbs off and lies down next to me. We kiss gently yet intimately and eventually fall asleep in each other’s arms.
The next morning when I awake, I am dreading the “well that was fun but that is all is was.” But to my utter delight this was not the case. This was the start to a new relationship. Over the next 6 months our relationship grew in so many ways. The sex was out of this world and she would often take me by surprise. Since we worked together, she would often take me into the ladies at work and have sex there. We had sex in the car in the parking garage and quite a few blow jobs while I was trying to drive. All in all one could say that I was living the dream.
8 months into our relationship we decided to move in together. I was worried that this might change things but I have to admit that things got even better. Instead of being with each other a couple of nights here and there and on weekends we were now with each other every night. The sex was awesome and frequent. Sally took me shopping and we purchased some sex toys. We started to experiment and soon I discovered that Sally was insatiable and was always looking for new ways to heighten the orgasms. She became almost possessed in wanting to try new things.
One day she came home with a strap-on and as she unpacked it and presented it to me I could see the look of excitement in her eyes. I was terrified at the site of it, not because I knew where it was going to be used but more so that it immediately brought Samantha’s experiences right back to the surface. I was so worried that she may discover my little secret. I pretended to be shocked and uttered that what she was thinking was never going to happen. She just smiled and said, “we will see.”
It did not take long. 3 days later while in bed and using a vibrator on her, she reached down and removed it from my hand. Lying next to me and kissing me gently she took the vibrator from my hand and slowly proceeded to used it on my hard cock. Then she pulled back and watched me intently as she slowly moved it down across my balls and then slowly continued till she reached my anus. I gasped and tired to tell her to stop. She smiled again and told me not to move. My mind and my hormones were raging by now. I could not hide the pleasure from her and she immediately knew I was loving it. She smiled at me and told me, “I knew you would enjoy this”.
Next came the lube and before I knew what was happening she was inserting the tip into my anus. I could not stop my hips from rising off the bed. This only seemed to egg her on more and then the vibrator was inside me and I could feel it going all the way in. Now I was totally at her mercy. She spent the better half of the next 10 minutes taking me to heights she had not yet seen. Then she told me she would be back but instructed me not to remove the vibrator. A couple of minutes passed and then she returned sporting the strap-on from a few days earlier.
I desperately tried to tell her, nooooooooooooooo, but I don’t think there was much conviction in my voice. She came over, slipped the vibrator out and instructed me to turn over and get on my knees. She lubed the strap-on and then it was pressing against my tight hole. I was waiting for the pain as it looked too big, but to my surprise there was none. The vibrator had certainly done its job and the strap-on slipped into my anus with relative ease. She was gentle and took her time sliding in. Before I knew it she was almost all the way in. Then she started to slowly work it in and out.
I was trying so hard not to show how much I was enjoying this but was failing miserably. Sally reached around to find my cock and it was rock hard and this seemed to just confirm how much I was enjoying it. She started to move a little quicker, her hands taking hold of my hips as she thrust deeper making me gasp. By now I could no longer control my excitement and started moving back to meet her thrusts. Then without warning my orgasm arrived. I seemed to lose all control and let out this moan from deep inside as my body shook and the explosion from my hard cock erupted with such force. The orgasm seemed to last longer too as is seemed to emanate from deep inside. Sally kept going as I stayed there on my knees soaking up the pleasure racking my body.
I found that all my senses seemed to be in overdrive and I noticed that I was still rock hard. Sally seemed to notice too and then suddenly pulled out, flipped me onto my back and immediately climbed on top of me, took hold of and inserted my rock hard cock up her pussy and started to move and grind away. I was amazed I was still so hard and she commented on the same. She smiled at me and said “now we know what you really like. Oh we are going to have so much fun”. I noticed that she was so turned on by what had just happened and it did not take her long to reach orgasm.
Little did I realize that this night was going to prove to be a turning point in our relationship. I was coming to realize that Sally was almost insatiable as far as sex went and she was wanting it more often and was becoming more and more daring. We even ended up having sex on a public beach with other families around. With her sitting on top pretending to rub suntan lotion on my chest, she moved her bikini to the side and slipped my cock into her pussy. She moved very slowly for ages like that trying to hide what was actually happening until we both climaxed.
The Turning Point
The big turning point came one day when Sally was sick and stayed at home. When I got home that afternoon she was sitting in the lounge watching TV and when I entered I did not get my usual hello. Thinking she was still not feeling well I went upstairs to the bedroom. As I walked in my heart sank. There, lying open on the bed was my secret little case I had all but forgotten about and all the lingerie spread out on show. Then her voice behind me saying in a not so friendly voice, “Care to explain this, why was this locked and hidden at the top of your cupboard?”
I was speechless and had no idea what to say. She came to my rescue by asking me if I always collected lingerie from my previous girlfriends. I took this as my cue to try and salvage the situation. I said no, only some and told her that I had actually forgotten about the case. I could see that she was not convinced. Over the next couple of days she persisted in pursuing the issue and wanting to know more about the previous girls and more so why I kept some of their lingerie. Eventually after 4 days of this and the cold shoulder in bed I risked everything and just told her straight out that the lingerie did not belong to any previous girlfriends. She looked at me and demanded to know where it was from and eventually I told her it was mine. She walked out the room calling me a liar and told me not to talk to her until I was ready to tell her the truth.
I sat there on the bed for ages not knowing what to do. I could hear her downstairs banging things around. Eventually I decided there was only one way to deal with this. It was time for Sally to meet Samantha. I slipped on some stockings with suspenders, panties, bra and one of the see through little nighties. Looking at myself in the mirror I was absolutely petrified.
With my heart in my throat I slowly walked down the stairs. Walking into the lounge and seeing Sally sitting there made this all seem wrong. She looked up and just stared without saying anything. It seemed like an eternity and then without saying a word she got up and walked over. She looked me up and down and then moved behind me. I had no idea what to expect and I could feel her eyes on me which felt like daggers. Then I felt her hand between my legs from behind. My cock was tucked into the panties giving me that real fem look. I figured that she should see me as I saw myself, as Samantha.
The she whispered in my ear, “So how long have you been doing this?” I decided there was no point in lying and so told her I had started wearing panties on and off since I was 7 years old. She starting asking more and more questions about why, when and who else knew. The questions were coming thick and fast and I was trying to keep up. I ended up telling her everything, including my time overseas with Lars and Anna. Then the accusations started. Why had I not told her and especially why was I so anti the strap-on initially when actually I had already been with a man and had my ass penetrated by a cock already. I tried to tell her that I was scared and embarrassed.
Her hand was now gently fondling my cock in my panties between my legs and I could feel myself getting harder by the second. She whispered in my ear again, “I can feel you like this.” All I could do was nod. She asked me to tell her all about my experience with Lars and Anna. At first I was very reluctant but a curt, “all of it and now” in my ear from her and I was spilling my guts. Throughout the entire story she continued to play with my cock in my panties and I could feel them starting to get very wet. At the end of the story she wanted to know my girl name. With that she instructed me to go upstairs and fetch the strap-on and the lube.
I returned carrying the strap-on and lube and handed them to her. She did not even attempt to undress. She attached it over her jeans while I just stood there watching. Then she instructed me to bend over the couch. The first thing I noticed was that the curtains were now open and I tried to complain and ask her if I could close them as the unit on the bank next to us was above us and looked directly into our lounge and also our bedroom upstairs and I knew there was a single guy of about 30 years old living there. She told me in no uncertain terms that the curtains stay open. Again I started to complain and she cut me off saying that she did not care if someone saw me for who I really was.
So there I was bent over the couch, looking out the window, praying that no one was watching. She slipped my panties down just far enough to expose my anus. I could feel her take some lube and using a finger, she slipped it into my hole and spread it around. Then I could see her applying lube to the strap-on. Then she is pulling my ass cheeks apart and I can feel the tip of the cock at my hole. This time she was not so gentle and I had not had the benefit of a vibrator to get me ready. I gasped and winced with a little pain and she shoved almost half of the cock into me. I tried to tell her to slow down but she told me to shut up.
I was a little scared at this point and still worried someone was going to see. She took hold of my hips and started to thrust a little faster. She kept saying things like, “so this is what you like hey?” and “I can’t believe that all this time I have being going out with and living with a little sissy boy!” I was desperately trying to tell her that it had not been like that and all I got back was, “Shut Up”. She continued to fuck me with the strap-on while all the time cursing me and calling me names. The worst part for me was I could not stop my excitement growing and within 10 minutes I was cumming and making a mess in my panties. I immediately felt shame and tried to hide the mess but she continued to fuck away as if nothing had happened. I could feel her anger in her thrusting.
Then I noticed movement in the unit above us. I tried to stop Sally and tell her but this just seemed to spur her on. She told me she wanted the man to see me and that I deserved it. It was almost like she was putting on a show for the guy. I was not sure if he was watching but she continued for another 5 minutes or so. Then she promptly pulled out, looked at me with what looked like contempt and told me to go and clean myself up. I walked up the stairs feeling like I had done something terribly wrong. As I walked into the bedroom I noticed the guy from the unit above looking straight into our bedroom. I quickly closed the curtains feeling even more embarrassed now.
For the next couple of days there was no mention of my lingerie and no more talk about what had happened. In fact things were quite cold and there was no sex at all in that time. By now I was so worried that things were coming to an end. I was also aware of this feeling that something in Sally had changed although I would later learn that it had always been there but I was the only one who could not see it.
4 days after the incident I was introduced to the new twist. I had a meeting to attend at work and only arrived home at about 6pm. When I walked into the apartment Sally seemed to be in a better mood and I even received a hug and kiss. I thought, yeah, maybe things are returning back to normal. She suggested that I go take a shower and then come downstairs as she has cooked a nice dinner for us. So off I went. I noticed when she came into the bathroom and picked up all my clothes I had left on the floor but thought nothing of it.
When I got out of the shower and walked into the bedroom Sally was standing there and I noticed a heap of small pieces of material on the bed. I asked what was going on and what the mess was on the bed. She leaned down and picked up a handful of the material and let it drop from her hand back onto the bed. She happily informed me that it was the remnants of the last pair of men’s jocks in the house that I had been wearing that day. When I asked her what she meant she promptly took my hand and led me to my cupboard. She opened the door and there in place of all my jocks was a whole stack of new panties, some new stockings, a couple of bras, new suspenders and a couple of new nighties and negligees. She then opened the other side of the cupboard to reveal a couple of dresses, miniskirts with a few blouses.
I just stood there speechless. I looked at her and she was smiling at me. She informed me that from this day forward I would never again wear men’s jocks and at home I would only ever be dressed as a girl. I was not sure what to make of this and again that fear arose within me. I asked her what would happen if I had to go see a doctor or something at some stage and needed a jab. She looked at me with this mischievous look on her face and said she was actually counting on it and would insist on being there to watch if it ever happened. I could see that she was really enjoying this and even though I was somewhat excited, deep down I was actually quite scared. She then informed me that there was another issue to take care of first. She took me into the bathroom and instructed me to undress and to sit on the edge of the bath. She told me that even though I did not have much hair, what I did have on my legs and under my arms had to go. I have to admit that this really excited me. 20 minutes later I emerged from the bathroom minus all the hair on my legs and under my arms and sporting a tiny little patch of pubic hair above my cock. God I felt amazing.
The sex that night was amazing, with all the toys being used and it felt like good old times with both of us having amazing orgasms. The next morning I was to realize just what Sally had in mind. Usually she would get up in the morning and let the maid in. I was rudely awakened with an elbow to the ribs. Rising from the depths of my slumber she informed me that it was now my job to go downstairs every morning and let the maid in. I tried to protest but dragged myself out of bed. I was wearing panties with one of the new nighties. I grabbed my dressing gown out of the cupboard but she stopped me in my tracks and demanded to know what I was doing. I told her I was going to let the maid in. She then informed me that I was not going to be wearing the dressing gown. She made it very clear that I was going down in just my panties and nightie. I desperately tried to tell her that there was no way but she made it very clear that from now on that is the way things work in this house. I could see the look on her face meant there was no arguing the point.
I proceeded down the stairs to open the door for the waiting maid. God this was more than scary. I tried to hide behind the door as I opened it and waited for her to pass before closing it, hoping to hell that she did not get a full view, although there was no hiding it all. I waited till she had gone into the kitchen before making my dash for the safety of the bedroom upstairs. All Sally said when I walked back in was, “Good Girl”. I headed for the shower not sure about this new role but also realizing that I was more than just excited in my panties.
When I emerged from the shower I was confronted by Sally and the maid in the room. Sally proceeded to explain to the maid, in front of me, that from now on she was to call me "maam" in the apartment and that I would only be wearing women's clothing at home. I was only allowed to wear normal clothes to work except for the compulsory lingerie underneath. Sally proceeded to show the maid all the new panties, other lingerie and clothing that now belonged to me. She made sure that maid understood whose clothing belonged to who. I felt so sorry for the maid and could see that she looked as embarrassed as I did. With that Sally took out some fresh panties from my cupboard, some stockings and suspenders and said, “You will be wearing these to work today Samantha”. With that she went and hopped into the shower leaving me to blush in front of the maid who then made a hasty retreat.
The sex from here on in took on a whole different role as Sally became more of a mistress than a lover. Sex at work in the ladies toilet at work became more frequent. Except now she would take me in there, make me sit on the toilet as she straddled me and she would slip my cock out the side of my panties and then ride me until we both reached orgasm. Then she would rise up and let all my cum ooze from pussy onto my panties. Then she would instruct me to not clean a single drop up and make me go back into the office with my panties covered in our cum. I was so sure that someone would notice but thankfully no one ever said a word.
Sex at home now almost always involved toys and the curtains in the bedroom and downstairs in the lounge were always left open. I know the guy living in the unit above us was watching us constantly as I had often seeing the curtains moving and almost always the lights would go off while we were having sex and then later they would come back on again. I tried to imagine what was going through his mind and often this would heighten my excitement. Sally also knew he was watching and would often say to me, “I wonder what that guy thinks of my little sissy?” She would often threaten that maybe she should invite him over.
I started to hear rumours that Sally was having a few flings with other people, especially in the office, but did not want to believe this. One evening I decided to ask her and she just smiled at me and denied it. The next day she came to me during our lunch hour at work and said we were going shopping. She took me across the road to a clothing store that sold everything from lingerie to all women's clothing. She told me I needed some real ladies jeans. She picked out a few jeans and took me off to the change rooms. I felt so embarrassed being in a ladies clothing store to begin with and worse was been made to try things on right there and then. She had me strip down to my stockings, suspenders and panties and had me try on the first pair of jeans. They were way too small and she said she was going to get a larger size.
A couple of minutes later there was a knock on the door and I opened it expecting Sally, but was horrified to find one of the lady shop assistants there with a pair of jeans in her hand. I think she got more of a shock than me. Standing in the background watching was Sally grinning like a Cheshire cat. The lady says my girlfriend asked her to bring me a bigger size, eyes me up and down in all my glory, hands me the jeans, smiles and leaves. Sally then walks into the change room and tells me to shut up when I started to complain. She has me try the jeans on and they are so tight fitting but perfect as far as she is concerned. She claims it gives me the perfect female form.
I eventually manage to get them off without tearing my stockings and then standing there she reaches down and starts to play with me in my panties. I tried to protest but again she told me to shut up. I could not believe how excited I was which Sally commented on by saying, “I can feel how much you enjoy this. You and I both know how much you need this.” She proceeded to make me cum in my panties right there and then which took only a couple of minutes. I was amazed how excited she was getting me these days. Then standing there with cum oozing out my panties she tells me that this is not good enough. I can’t go out there like that. She disappears and comes back shortly thereafter with some brand new panties. In her other hand is a clear plastic bag of sorts. She instructs me to take off my cum soaked panties and to use them to clean myself off properly. Then she instructs me to put the new panties on but only after she has removed the tag and then to meet her in front to pay.
As I am walking to the front where the till is to pay, I can’t help but notice the looks and whispers going on between the two girls there. Sally is standing outside the shop watching me, again smiling at my discomfort. When I get to the counter to pay, I see there the jeans are there and 2 other pairs of new panties and then to my horror I notice the cum soaked panties lying in the clear plastic bag for all to see. Both girls are smiling and the one starts to ring up the items. Then she picks up the tag from the panties I am now wearing and says to me. Did you girlfriend give you the other panties? God I wanted to run. I just nodded. There are 3 people standing behind me and by now I know I am blushing. To me, the lady ringing things up seems to be taking ages. She puts all the new things into one of those bags without handles on it and then fucking staples the bag closed. She then holds up the see through bag with my cum soaked panties in for all to see and hands them to me before handing over the bag with the shopping. Clutching the bag with my cum soaked panties against my body and hiding them with the shopping bag I made a dash for the door.
Once outside I was about to lay into Sally when she takes me by the arm and leans in and says to me. “Don’t you ever question me again, do you understand?” I was not sure how to respond. Then I remember how I questioned her about the so called flings. Then she tells me that at least the girls in the shop would have something to talk about now.
I was still upset that evening by the time we got home. I think she sensed this and decided to ratchet it up a notch. Over dinner she asked me if I had ever had a 3some. I reminded her about Lars and Anna and then she said, “No with 2 women?” I said no. She asked me if I had ever thought about it and I told her that I am sure that most guys have fantasized about it at some stage in their lives. She then told me she wanted to try a 3some with another women and me. I was taken aback but by now I had realized that Sally never did or said anything that she had not already thought through. So when I asked her where she was going to find this 3rd person she immediately told me she had been chatting to a girl and that she was keen. Now I knew it was happening whether I liked it or not. So I just said it sounded like a wonderful idea.
2 days later it happened. Sally left work saying that she had a meeting to go to. When I got home at 5:30 her car was there. When I walked into our apartment I noticed she was not downstairs so climbed the stairs to our bedroom. Before I even walked in I could hear women's voices or more to the point sounds coming from more than one women. As I walked in, there on our bed was Sally with this other women and they were both naked and going at it. All I could do was stand and watch. Then Sally stops and says hi and then introduces me to Tracy. She tells Tracy that this is Samantha the one I have been telling you about. God I just wanted to hide. Tracy says hi, and then Sally says, “well don’t just stand there, get undressed and you can sit on the end of the bed and watch till we are ready for you.”
For the next 30 minutes or so I sat on the end of the bed in my panties, stockings and suspenders and watch as Sally and Tracy took turns licking each others pussy's, fondling each other’s breasts, kissing and then using the virbrator and dildo on each other. I watched as they both had orgasms. Sally would keep looking over at me and smiling. By now my hormones were raging and eventually Sally turns to me and tells me to come over. She wants to watch me with Tracy.
She guides me down between Tracy’s legs and instructs me to lick her pussy. I am so excited having watched the two girls for so long. My head is buried between Tracy’s legs and my tongue us working her clit. Hearing her moans of pleasure only heightens my excitement. Then I feel Sally’s hand between my legs and she starts to fondle me in my panties. I am hard and wet and Sally then slips my cock out the side of my panties and starts to work my cock over with her mouth. I am in heaven. After about 5 minutes Sally says to me that she wants me to fuck Tracy. She has me move on top of Tracy and she guides my swollen cock into Tracy’s wet pussy.
I am thrusting away and Sally places her hand on my panty covered ass and starts to push as I thrust down pushing me even deeper. Then she is whispering in my ear, “ Don’t you dare cum inside her Sissy”. I was so close but knew better so was trying everything possible not to cum. Then out of the blue Tracy has an orgasm and Sally smacks my ass and pulls me away telling me that is enough. Then she gets up and the next thing I know she is putting on the strap-on. She tells me to get on my knees and to lick out Tracy’s pussy juices. I do as told and I feel her slipping my panties down just far enough to expose my anus. She slips my throbbing cock back into the front of my panties and then I feel the strap-on cock at my anus. She has already lubed it and before I know it she is inside me. She tells me not to stop licking Tracy’s pussy as she sets about fucking me, telling me this is all I deserve. 5 minutes later and she has me cumming so hard. Tracy is now lying there watching me with interest. When at last Sally pulls out of me, she calmly tells me that I can now leave and go downstairs and leave the girls alone. Feeling really humiliated I leave and for the next hour all I could do was listen to the sounds emanating from upstairs as the two of them are going at it again. Sally was adamant that I hear every orgasm they experienced together. So much for the 3some.
When they were done they came down stairs and Sally informed me that she was taking Tracy home and that I should sort out my own dinner. That was at about 7:30pm. I sat there seething and by 11pm when she was still not home I eventually climbed into bed. At 1:15am she eventually arrived home and made a point of waking me. When I questioned her as to why she was so late she informed me that when she got to Tracy’s place her husband wanted to know where she had been. Sally was only too happy to inform me that she had ended up in another 3some with Tracy and the husband. This had me furious, but Sally was quick to point out that if it was ok for me to fuck another man’s wife how could I be upset if that man fucked her (Sally). Once again I was told to shut up and grow up and with that she promptly turned over and was asleep within 5 minutes. I lay there a long time thinking about what had just transpired. The real Sally was coming to the fore and I was not sure how to handle this.
The next morning I was still not ok with the situation. I tried to explain this to Sally and told her that if I had known Tracy was married I would never have agreed to it. Sally seemed not to hear me and all I got was, “well you seemed to enjoy it, so get over it.” Then she tells me that Tracy’s husband was also not very happy about it. But she believes that by having sex with him seemed to calm him down so I should be thanking her.
The Angry Husband
Little did I know that I was in for a surprise? 2 days later I arrived home and there parked in my spot was a strange car. Immediately all my alarm bells went off. I entered our apartment as quietly as I could. As I walked up the stairs into the lounge, there was Sally sitting with this guy. He was drinking a beer and Sally was sipping on a glass of wine. Sally smiles but does not get up and she introduces me to Derick, the husband of Tracy. She just sat there watching and smiling at me.
Eventually he says, “So you are the little bitch that thinks he can fuck my wife?” I was speechless. I then tired to apologize and tell him that I did not know she was married. I looked to Sally for some help but immediately realized this was pointless and I could plainly see that she was loving every moment. So, “Sally has told me all about you”, Derrick says to me. “So you are a little fag”, he says. I so desperately wanted to just leave. Then I notice that on the coffee table was an array of lingerie, a pair of heels I have not seen before, a new wig and some makeup and other odds and ends. He must have seen my gaze and then he tells me to undress. I just looked at him in disbelief and shook my head.
Without warning he gets up, walks over to me and smacks me with an open hand brining instant tears. He tells me he is not going to ask again. I look at Sally and can see I am not going to get any help there. With tears running down my cheeks I start to undress until I am standing there in just my panties, stockings and suspenders. He asks me if I go to work like this every day and I just nod. Then he tells Sally to do her thing. She gets up and hands me a bra and helps to put it on. Next is a negligee and then I am instructed to sit on a chair which I then realize has been specially placed there facing the couch. Sitting, Sally crouches and slips the new heels on me. I am too scared to even ask where these have come from. Then she tells me to put my hands out and she goes about painting my nails a bright red. Next was the makeup which she spent about 10 minutes applying and then finally the new wig. All I could think of, was not being there. Then she stood back to admire her handiwork and asked Derrick if he approved. He stood up, walked over, looked me over and then said I looked like a real little sissy fag now.
Then he removed some handcuffs and without warning slipped the cuff over my one wrist and snapped it shut. Now I was terrified. He took my other hand and pulled it behind the chair and handcuffed my wrists together. Then he picked up 2 ties from the coffee table and proceeded to tie my legs to either side of the chair. Then he said “now we are ready.”
With that Derrick and Sally returned to the couch and purposefully started to kiss and make out. His hands were all over her breasts and the sounds she started to make were most definitely for my discomfort. Tears were still rolling down my cheeks and I was doing everything not to make a sound. I just watched the 2 of them. His hand now between Sally’s legs, her skirt hitched up, panties exposed. His fingers working her clit through them. I could see the wet patch forming. Her moaning becoming louder.
Then he moves her panties to the side and his finger slipped into het wet pussy. This prompted her to reach over and I could see the bulge in his pants. She unzipped him and proceeded to take his cock out. Fuck it was huge. She started to stroke his monster while he fingered her. Then there were 2 fingers in her and her moaning was getting louder by the second. Then she was leaning over and his huge cock was in her mouth. She licked, teased and then took as much of his monster cock into her mouth as she could. He sat back and watched me watching them. I could not take my eyes off his cock. After 5 minutes of Sally working his cock with her mouth he told her to stand up. He looked at me while he then slowly stripped Sally removing her panties last. Then he had her turn around to face me and straddle him and then lowered her down onto his cock. With them both watching me now she started to very slowly move up and down and grind on his huge cock.
All I could do was sit there and watch his monster cock going in and out of Sally’s pussy and listen to the sounds coming from her. I was mesmerized and for the next 10 minutes or so Sally rode his cock and made sure I knew just how much she was enjoying it. Derrick never took his eyes off me and then said to me, “you see how a real man fucks a women”. I felt so useless.
Then Derrick is lifting her off his monster cock. I can see how big and strong he is and my face is still stinging as proof. He tells her to come sit on my lap facing me. He stands next to her and tells her it is time to show this little sissy fag how it is done. His cock is right in front of my face. He tells Sally to show me how a real girl sucks a cock. She takes his monster cock and starts to slowly lick, and suck on it a mere 3 inches from my face. I can see her pussy juices on it still. His hand is on her head guiding her telling her how good she is at sucking a real mans cock.
After about 3 minutes he pulls out and then says to me, “right Faggot Bitch it is your turn”. I started to say no but before I could even finish he raised his hand and I immediately moved forward not wanting another smack. I opened my mouth and then his hand was on my head guiding his cock into my mouth. Sally was almost beside herself with glee. I could see just how much she was enjoying this. Derrick now telling me what a good little faggot bitch I am. Gagging as he shoves more of his monster cock into my mouth. Now Sally reaches down to find my hard cock in my panties. “This little slut likes this”, as Sally tells Derrick that my little cock is hard and that my panties are so wet. He looks down at my panties and tells me what a useless pathetic little cock I have and it’s not worthy of fucking a women.
Derrick is now holding my head and starting to thrust his monster cock into my mouth with a little more force. Sally is working my cock in my panties a little more urgently now too. To my horror I can feel my excitement building. Derrick telling me what a useless little faggot bitch I am. Sally telling me what a good little cock sucker I am. Suddenly I can’t contain myself anymore and with a loud moan I am cumming in my panties. Derrick looking at me and then telling me how sad I look, pulling his cock out of my mouth and saying that I don’t deserve it. Sally laughs at me and lifts her hand covered in my cum and tells me how pathetic I am. She asks me how I can cum in my panties sucking another man’s cock and tells me I am not worthy of fucking a real women like her. She goes on to say that from now on I am only going to watch her getting fucked by real men and that the only use she has for me is to see me sucking cocks and getting fucked by her strap-on or even other men. God I feel so ashamed. To make matters worse Derrick then instructs me to lick Sally’s fingers clean, saying to me, “that a sissy faggot bitch like me should always clean up afterwards.”
Derrick then takes her and makes her bend over facing me with her hands on my legs. He fetches her panties from the floor by the couch and picks up another tie from the coffee table. He comes over and instructs me to open my mouth. He shoves Sally wet panties into my mouth and then puts the tie around my head and secures them in place almost gagging me with the panties. He then stands behind Sally, slips his monster cock into her wet pussy and starts to fuck her. He is telling her to tell me what it feels like to be fucked by a real man with a real cock and she happily complies. Not even 5 minutes in and her nails suddenly dig into my legs and she has one almighty orgasm. I had never heard that sound that came out of her before and now knew that things would never be the same again between us. He continues to fuck her harder and harder long after her cries of pleasure started to subside. Suddenly he pulls out, moves past her and grunting strokes his monster cock as he explodes all over my face and down my negligee. My god I have never seen so much cum. Then he takes his cock and rubs it all over my face. I can feel his cum dripping down my face.
Once he is done, he walks back to the sofa, finishes his beer and gets dressed. Sally just sits on my lap, spent and ignoring me. When he is done, he walks over, leans down and tells me if he ever finds out I have fucked his wife again I am in trouble. He warns me that he has friends that are cops and he will have them take me down to the police station and god knows what would happen then. He tells me that he will be visiting Sally again as she no longer had the need of my useless little cock and maybe next time he is going to fuck me too.
With that he removes the handcuffs, stands up, takes Sally and lifts her up, kisses her deeply. He thanks her and tells her he will be seeing her soon and then leaves. Sally looks at me with these sad eyes, leans down, kisses me on the cheek and says, “So my little faggot sissy, you know what you are in for now.” And then leaves me there to untie myself. I could not bring myself to go upstairs and slept on the sofa that night.
After that evening, things with Sally really changed. I was no longer allowed to touch her without her telling me what she wanted and in fact the only penetration that took place was her using the strap-on on me and always in plain view of the unit above us. She was often not home in the evenings and when I asked where she had been I was either told to shut up or it was none of my fucking business. Sex in the office was non-existent too and the rumors about her were now rife. This went on for another 9 weeks and then one day she told me she was not going to work. When I arrived home that evening she was gone. All her things including some of my furniture were nowhere to be found. I tried to get hold of her without success and none of her friends would tell me where she was. She just vanished.
At work the next day I was informed that she had left the company and only then did I really find out what had been going on. Everyone seemed to know what she had been up too. She had been sleeping with two of the bosses who were both married and their wives had found out and all hell had broken loose. I would never hear from Sally again. At first I was a lost soul, not knowing how to react and what to do but in the end there was a silver lining.
I did not go home and throw out all of Samantha’s things. I did however go out and buy a couple of men’s Jock’s just to be on the safe side. As it turned out I embraced Samantha again and even the maid became comfortable with who I was. I no longer felt embarrassed knowing she was doing the washing and knowing about me. I did however wear a dressing gown when letting her into apartment in the mornings. I also became comfortable with leaving the curtains open and walking around the apartment as Samantha knowing full well that the guy above me often saw me dressed.
The Silver Lining
And this is where the silver lining came into it. About 6 weeks after Sally had left, I was sitting out on the veranda one Saturday morning having a coffee and ciggie in my dressing gown. I noticed the guy from the unit above in his garden and it looked like he was trying to look busy, but really it looked like an excuse to just be out there.
He said hi and I greeted him back. Then he came to the fence and asked if everything was ok as he had not seen my girl friend around for a while. I informed her that we had broken up and that she was gone. He said he was sorry to hear that and then said if I ever need to chat I was welcome to knock on a friendly neighbour’s door anytime. Then all the thoughts of what he must have witnessed rushed through me and I was suddenly feeling very embarrassed. I am not sure what possessed me at that moment but I apologized to him for anything he may have seen or heard and hoped he was not offended.
To my surprise he smiled and told me that it had been an education watching us and to be honest he was not offended at all. Then he went on to say that maybe Sally leaving was not a bad thing. I got the feeling that he was really pleased she was gone. Then he suggested that maybe sometime we should have a drink and before I knew it I was saying, what about this evening. His face lit up and said, how about 7. He offered to come to me. With that he left me to my coffee and ciggie. I sat there thinking, “What the fuck did I just do?”
As the day wore on, I actually thought about it more and eventually came to the conclusion that he had approached me which he would never have done if there was an issue. In fact the closer we got to the time the more excited I got. Then I started thinking about what he had seen watching me and Sally all this time and what he expected and especially what I was meant to be wearing. I then decided that since he had seen me as a girl I should not worry too much. I did however make sure that my legs were shaved etc and decided that I would wear men’s jeans with a T-shirt but underneath I would be wearing a corset with stockings and of course the sexiest panties I had. I decided on the corset as I wanted there to be a hint of something under my T-shirt without looking as obvious as a bra. Then to finish it all off I decided a little perfume instead of men’s deodorant would definitely raise questions. I was feeling really daring and naughty by now.
6:50pm and there is a knock on the door. Luckily this girl was not running late. Opening the door he apologized for being early. He put his hand out and introduced himself for the first time (Out of respect I will not name him). I used my male name and then we made our way upstairs. I offered him a beer or glass of wine and he opted for the beer while I poured myself a glass of red wine. I offered to sit outside as it was a beautiful evening and of course my nerves were getting the better of me and I really needed a ciggie. We sat and I asked him if he minded if I smoked and he said not at all and he produced his own cigarettes.
The conversation at first was a little awkward. I asked how long he had been staying in the complex and where he was from and what he did for a living etc. It was as if both of us knew that we were getting to what he had been watching all this time. At some point there was an awkward pause in our conversation and so I got up to refill our drinks. When I came back I noticed that he was staring at me. I asked him if something was wrong. He said no and then opened that door we had both been avoiding so far by saying, “I was just wondering what you are wearing underneath and what perfume you use?” And there is was. I must have blushed because he then said, “well I am sure it is not anything I have not already seen?”
It was a revelation to have it out in the open. My next drink went down way to quickly and I needed a refill. When I arrived back and before I could sit again he said to me. “Why don’t you go upstairs and change into something more comfortable and fitting?” I looked at him, blushed again and then said I would be back as soon as possible. Told him this girl needed about 20 minutes and he told me not to rush. I told him to help himself to the beers.
Once up stairs I decided on a short mini skirt with a flowery blouse and then took out my heels. I decided that some make up was necessary which I had become quite adept at applying along with the wig and painted nails. 25 minutes later I walked down stairs again and stood in the doorway leading outside. He sat there smiling and said “wow” and asked me to do a pirouette for him slowly. Then he asked what he should call me and I introduced myself as Samantha. He stood, took my hand and kissed it and said he was so pleased to meet Samantha. God this felt so good.
I found some snacks and we spent the next couple of hours just chatting and I found out he was actually gay but he had not been in a relationship for 2 years. I told him almost everything about Samantha. He was so easy to chat to and eventually I asked him how he felt about a girl like me. He admitted that this was something totally new to him as he had only ever been with other men since the age of 22. He had tried dating a couple of girls before that but they had never really done anything to excite him. He had known since he was 14 that he was gay but like a lot of gay men they try and either ignore or deny their feelings due to public perception.
By now the alcohol and the chat was having an effect on me and my excitement levels were increasing rapidly. I could feel the wetness in my panties spreading and then I asked if he would like to go sit in the lounge which he happily agreed to. Walking in I closed the door and for the first time in a long time, closed the curtains. He sat on the sofa and I went and sat next to him. I turned to face him and I noticed his gaze slip down to my skirt. I realized that my skirt had crept up and that my panties were showing. I went to adjust my skirt and he put a hand on mine and told me not too. I looked at him and he told me he liked the view. He then leaned in and before I knew it his lips were on mine.
The first kiss was so gentle and then he pulled back and said that he had been wanting to do that all night and asked me if it was okay? I was speechless and reached up and placed my hand behind his head and slowly pulled his lips back to mine. His lips on mine, my tongue gently leading and searching, his mouth opening and our tongues finding one another. That kiss lasting forever, so sensual and yet filled with a passion I had not felt in some time. This was so different to Lars and most definitely Sally. I had not been with a man like this before.
Then he pulled back, looked at me and then stood and without saying a word took me by the hand and led me upstairs. In the bedroom we stood as we kissed and his hands explored my body. He very slowly removed my blouse, and then getting on his knees, kissed my legs through my stockings as he slowly removed my skirt. Then clad in my lingerie and leaving my heels on he lay me down on the bed. By now my hormones were doing cartwheels and I just wanted to feel him, to hold his hardness but he urged me to wait. I lay there and watched as he undressed, totally naked, revealing his sexy body to me. Oh my, he had the most beautiful cut cock about 6 inches and not too thick, pretty much the same size as mine. Hard already with a gorgeous head.
He spent the next 30 minutes or so exploring, teasing and taking me to new heights. My panties were soaked with precum by now and he was down there exploring my hardness through the satin material. Then he was very slowly removing my panties, freeing my hardness and then I was inside his mouth. Oh my fuck this was too much. Then he gently rolled me onto my stomach and his lips were on my inner thighs, gently working their way up.
My body was now aching for him and then I could feel my ass cheeks being slowly prised open and then the first flick of his tongue. I could not control my moans of pleasure now and then his tongue is probing and I feel it slip just inside my anus. The next 5 minutes are a blur as he works my tight hole. Then he rolls me onto my back, lifts my legs to my chest to expose my anus some more and goes back to giving me this pleasure that is driving me crazy.
The next thing I know he is kneeling between my legs, holding his hard cock. I am thinking he needs some lube but when his cock reaches my hole I realize that I am so wet down there now that it won’t be necessary. He is ever so gentle, first his head and then very slowly he enters me all the way. He is looking at me with his hands holding my legs against my chest as he slowly starts to move. Fuck he feels so deep. He leans down and kisses me deeply before going back to his kneeling position. My breath coming a little faster now and my moans getting a little louder he starts to move a little quicker. My whole body is starting to tingle and I can feel my orgasm building from deep inside. He senses this and then starts to move faster and suddenly I grab him by the wrists trying to pull him deeper into me and this moan of absolute uncontrollable pleasure escapes me as my orgasm takes hold. My whole body seemed to go into orgasm as he continued move faster now. A couple more strokes and he starts to jerk and hold me tightly as he explodes deep inside me. He continued to hold me like that until he has finally released all of his manly juices deep inside me. Finally he pulls out and I can feel his juices inside me and some of it easing out of me. The thought of a condom had not even crossed my mind and as it turns out he was safe as I later found out.
He lay down next to me, turned and gently kissed me without having to say anything. We lay there for a couple of minutes just enjoying the moment and then I took his hand and whispered, “ that was beautiful, thank you.” He turned and looked at me and said, “No that was perfect.” He spent the night and the next morning before leaving we made love again but this time he allowed me to touch him and explore his body before he again penetrated me. To my absolute delight he preferred being a top and had problems with me never wanting to penetrate him.
For the next 14 months we had the most amazing relationship spending most nights together and in all that time I never even considered being with a woman. He was the perfect gentleman and just the right guy for me at that time. But like most good things in life there sometimes comes and end. After 14 glorious months he told me that he was moving to PE as his company was promoting and transferring him. It was a really sad day but I will never forget him and will always be thankful to him for entering my life when he did.
So a huge thank you goes out to him for helping me along my journey. If he ever reads this he will know who he is.
Next story in series: Crossdress Fun