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Sissy Boy Wimp pt 2

"My wife takes my feminisation further."

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My wife encouraged my feminisation more over the next couple of weeks. She often had me dressed more girlie whenever we were alone at home. I even had to wear a bra while I was dressed and she took great delight in fondling my breasts and patting me on the bottom as I went past her. She even complimented me if I did something right saying I was a good girl.

You’re now thinking about how I felt about all this.

Well, the truth is, I had mixed feelings about it all. Being made to wear panties at the start awakened my interest. The feel of the soft wispy material around my cock and hugging my bottom felt quite erotic and I’ve worn them ever since. My wife encouraged me to do so and I would not have argued with her anyway, but I have to admit that I grew to love it and it made me feel quite sensual.

As for being fully dressed as a female. Well, It was a shock that she would want to see me dressed that way, but she did, and once again, after initial embarrassment, I quickly got used to it. I had to learn how to walk while wearing a skirt or dress in a more feminine way and with practice and encouragement from my wife I stopped looking awkward as I moved around the house. Once again I was a “good girl”.

Now the sex bit.

It was very strange being fucked and not the one doing the fucking, but with the help of copious amounts of wine, I allowed myself to suck my wife’s dildo and let her mount and peg me. Having never done or contemplated any intrusion into my rear end before, it came as a shock. But I have to secretly admit that by the time she had finished thrusting the thing in and out of me, I began to enjoy the sensation of it. Despite the initial pain, I really began to enjoy my subservient role and I was so turned on I nearly pulled the end off my cock wanking it that hard during it.

During the course of the following two weeks, my wife had her hand up my skirt several times feeling my legs above the stocking top and she always stroked my bottom every time I walked past her. I’m not sure whether it was to keep me or her in an erotic mood but it definitely worked for me. I even got to the point where I would stick my bum out at her for fondling as we passed each other.

I experienced the dildo another four times during that time and by the fourth time I found myself reaching round and helping her to guide it in. On that occasion, I was really getting a very good sensation, to the extent that I orgasmed without having to touch myself. This came as a great shock to me but my wife smiled and later teased me about enjoying it too much.

She was right I was enjoying it a great deal. I had experienced something that liberated me sexually and, what’s more, was encouraged to do so by my wife.

I’d always been a back-of-the-room sort of guy, never wanting to push myself forward and happy to do as my wife wants, and she wanted this from me. I’d previously never thought of taking a feminine role, but now I’m in it I wouldn’t have it any other way. From the point of my orgasming from my wife fucking me with her dildo, I really began to admire her more and thank her for liberating me from not having to pretend to be more masculine anymore.

She did tell me there was more to come and if I wanted out of it then I should say straight away. Normally at this point, I would dither. Making decisions had never been easy for me, but after a few weeks of being feminised and controlled by my wife and loving it, the answer was “yes”. What she wouldn’t say was what was next.

The following weekend was like the previous ones. I was sitting next to my wife on the couch on Saturday evening after more shopping to add to my feminine wardrobe. We had eaten and we were working our way through a bottle of Italian Merlot. As usual at the weekend I wasn’t wearing my manly clothes but dressed only in a pink chiffon nightdress which was sheer and looked see thru, white fluffy slippers, and apart from make-up a painted nails, very little else.

My wife was sitting beside me with one arm draped over my shoulder and the other hand stroking my thigh. Like the previous weekends, I expected her to have sex with me sporting a strap-on that was going to penetrate my eager rear end.

A knock on the door alarmed me and in real panic I ran upstairs, leaving my wife to answer it. My heart was beating so fast and I flew up those stairs much faster than I could have thought possible. As much as I liked my new feminine life it wasn’t for public consumption so I beat a hasty retreat to the bedroom and waited until the coast was clear.

After a few minutes, my wife called me to come down saying it was safe for me now. Relieved I went downstairs still wearing my chiffon nightwear and fluffy slippers and expected to return to the point where we were before the knock on the door. As I entered the lounge I spotted someone sitting on a chair in the corner. Once again, In a panic, I attempted to dash out of the room but my wife had closed the door behind me and barred the way out.

I really panicked then and some of the language I used in the throes of it embarrasses me now, but it was my worst nightmare. I went to grab a throw from the settee to cover myself up. Meanwhile, my wife had both her arms and palms up at me urging me to calm down.

In my panic, I tried to ascertain what was going on but they both just smiled at me and waited until I had my breathing under control. She introduced him as Mark and that he liked that I wanted to “dress”, and wanted to get to know me. It appeared that Mark worked at the same office as my wife and that he had confided in her that he liked to “dress”, and was interested in others who did the same.

As I stood there gawping at them and wondering what was going on, my wife took the throw off me and I stood there in my see thru nightie covered in makeup and nail varnish not to mention the white fluffy slippers. My wife gave me a large glass of wine and I downed it very quickly. She explained to me who Mark was and that he would like to get to know me better and that I was to do as I was told and not object to anything that either of them wanted.

In a state of shock, my wife led me back to the couch and sat me down in the middle with her on one side of me and Mark on the other. I’m now like the filling in a sandwich with both my wife and Mark on either side of me stroking my legs and sliding their hands under the night dress.

I was in shock. I would never have dreamt that this was going to happen but I was being seduced by two people and one was a man. My wife could feel how tense I was and urged me to relax and start to enjoy the attention. Any sort of an erection I’d had disappeared as I wondered whether my wife would start calling me a gay sissy boy now but she urged me to keep calm and go with the flow.

My role was to do as I was told and I did. The leg stroking intensified as they both put their arms around my shoulders. Their heads turned towards me and they both started to kiss my face, my wife whispering to me that I was to let whatever happened, happen.

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But what did happen was Mark slid off the settee to end up kneeling in front of me with both hands on my thighs and working his way up to the top. His head went down and followed his hands so that my nightdress was lifted towards my waist.

Instead of caressing my thighs with his hands, Mark began to kiss and lick up towards my cock which still hadn’t recovered from the shock of the unexpected visitor. He then deftly took hold of it and guided it into his warm mouth and gently began to suck. It felt very comforting and my cock began to rise again.

Thinking I shouldn’t be allowing another man to be gorging on my cock, I turned to see how my wife was reacting. She just smiled and stared down at Mark’s bobbing head on my cock. It was clear that she wanted this to happen to me, so I closed my eyes and let the sensation carry me along. My erection was complete in no time and the feelings it gave me only increased my levels of lust and I let it all happen.

But before it did all happen my wife told Mark to stop and made me stand up. was standing in the middle of the room wearing a pink nightdress and fluffy slippers sporting a cock that tented out the nightdress and both she and Mark were stroking me all over. My bottom came in for a lot of attention from Mark and it didn’t take a genius to realise where this was going to end.

Following directions from my wife, I was to kneel down on the floor and Mark pushed me forward so that I was on my hands and knees. He was then ordered to undress in front of me and I was to watch. I paid a lot of attention to Mark taking his clothes off as I was worried that his cock would be too large for me to take. Though it was larger than mine it looked about the same size as my wife’s strap-on.

Relief.

Mark was now standing in front of me naked. My wife then started to urge me to take Mark's cock in my mouth and taste it. I was surprised because although my wife is quite assertive with me she is usually a lot less so when others are around. But there she was, ordering a naked man and a sissy boy around and telling them what to do.

As Mark’s cock got closer to me, my wife jumped off the settee and knelt down so that she could clearly see his cock entering my mouth. As it did she started calling me a Sissy Boy again and urging me to take it all in and give him the best blow-job he had ever had.

I tried very hard to do as I was told but there is a difference between a silicone strap-on and the real thing. For a start, the real one was warmer and it reacted as I let it slide in and out of my mouth. This was the first real cock I’d ever had in my mouth and without trying to give it away I was really enjoying it. I wasn’t sure whether my wife was doing this to humiliate me or not. If she was it wasn’t working.

As I slurped away at Mark’s cock and listened to his moans, my wife slipped out of the room only to return a couple of minutes later naked under a flimsy dressing gown and wearing the strap-on dildo.

Yet again another shock. I believed that up to her appearing naked in the room I was the only other person who had seen her without clothes in her adult life. Yet there she was in front of another man and me, as brazen as I’ve ever known her, nude and sporting a strap-on dildo.

There was no time to ask questions as she handed Mark a condom and lube and he withdrew his cock from my mouth only to have it replaced with my wife’s strap-on. As Mark moved around to my rear I’m bracing myself for what I know was going to happen. Sure enough by the time the cold lube was smeared onto my hole, I was ready. I looked up at my wife and she just smiled and nodded to Mark and I felt him gently pushing at my bum hole.

Little by little he entered me setting up a slow rhythm that was echoed by my wife pushing the dildo into my mouth. The rhythm increased gradually and reached a point when all my wife had to do was stand there in front of me and let Mark thrust me forward as he thrust himself into me. I was being spit-roasted and my very stiff cock was telling me that I was enjoying it.

All the time this was happening to me, both Mark and my wife became quite verbally aggressive toward me. They both called me names and tried to humiliate me. Mark even slapped my bum cheeks a number of times and I was getting more and more worked up with very mixed emotions as the rhythm and intensity of Mark thrusting into me increased.

Meanwhile, my wife had stopped insulting me and began to urge Mark to even greater intensity as he rammed his cock into me as deep as he could aggressively go before he came, with a loud grunt, inside me. I have to confess that the last part of my being fucked was at best, a little uncomfortable. Actually, it hurt a bit but not enough to make me scream.

As Mark collapsed on top of me my wife pulled the dildo out of my mouth, knelt down in front of me and kissed me quite passionately for her, and told me that I was a good girl and that she was very proud of me. I tried to smile back but it was just at the same time as Mark removed himself from my bottom and I winced. She indicated that it was time for my reward, and with that, she ripped off the dildo and lay back onto the settee with her legs spread wide and inserted it inside herself while I watched.

Another first.

I’d never seen my wife masturbate before and with another cock albeit a silicone one but I did find it quite a turn-on and my own hardened as I watched. She then withdrew it from her pussy and told me to enter her as quickly as I could.

I didn’t need to be told twice and I had my cock as deep as I could inside her and with an eagerness I’d not felt for a long time. This eagerness was reflected in the effort I put into thrusting myself into my wife. I’d never been so manly before, which was funny as I was dressed very girlie, but I really rammed home my cock and was extremely keen to plant my seed inside her.

Meanwhile, Mark had recovered enough to get up beside us as we were going hammer and tongs into each other. He put one hand on my wife’s left breast and another on my bottom cheek and pushed me hard into her. I knew I wouldn’t last very long and indeed I didn’t. My orgasm, when it came, was very intense and I couldn’t move for a couple of minutes. My wife too looked exhausted as I slid off her onto the floor.

Mark hadn’t finished either. His mouth made its way to my spent cock and he started to clean me up with his tongue. I was really sensitive by then and the tongue-lashing he gave me made me buck and squirm. I looked towards my wife who was staring at Mark cleaning me up and she pointed at her pussy and indicated that I should do the same to her.

As I always did what I was told, I did it with relish.

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Written by spenny134
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