Crossdressing, Why Me? Ch. 02

My aunt had moved out of my flat a while back and although I was missing borrowing her wardrobe living alone had given me other opportunities which I was to grab with both hands. Living alone allowed me to be as free and easy to dress in lingerie as often as I wished, which was virtually a daily occurrence.

By then I had purchased quite a range of lingerie. I had many pairs of panties of various styles and colours. I am very particular though, the bras have to match my panties exactly in colour and fabric. I do love black as it is one of my favourite but white is ok, but I love sexy red which is readily available. In truth though I like pastel colours like pale baby blue, lemon and of course the very truly feminine pale pink!

Whenever possible I like a suspender (garter) belt that compliments the look because even though I am more than happy to wear tights (pantyhose) but for sex and masturbation stockings suit much better. They also have a much sexier look. I like to wear lace topped hold up stockings when I cannot wear a belt to complete my femme ensemble. If you buy the very fine denier they both look and feel sensational.

Sometimes I wear panties and hosiery to work which gives a lovely sensation all day long, keeping me in a semi aroused state until I return home when I cannot wait to take my outer clothes off and wank myself to a lovely overdue climax.

I also had by then, and still have, cami tops and chemises with matching panties. To slip on a pair of panties is still for me one of life's true pleasures. The only difficulty I have sometimes is fitting my ever hardening clitty in to them for by the time they are around my ankles I am already half stiff in anticipation of what is to come. As I put on my matching bra I am getting quite horny and can feel my heartbeat rise. On occasion I can even get a little breathless.

Pulling a chemise over my head is delightful too. If I am naked underneath the feel against my dick makes it stand so proud and hard. It is so erotically lovely next to my skin.

One day I had a friend round my flat who commented on why I had some ladies lingerie drying near the radiator. I hadn't thought about it when he came round as I was so used to it being there. I had to think quickly and say that it was my girlfriends who had been staying over. I think he believed me but it taught me to be more careful in the future.

Back to my tale which is true in most aspects. In those days back in my flat when dressed in sensually sexy lingerie, and maybe a satin housecoat, I would lounge around watching Transvestite, Shemale, and CD porn on my computer as I leisurely caressed myself. I would allow my hands to wander all over my body never quite getting used to the wonderful sensations. Doing so has never lost the power to deeply arouse me in a way that nothing else ever has. I could get so hard and so turned on.

Watching others on video dressed like me doing sexual acts with others, whether male or female, was exciting but was unsettling. I wanted some of the action! I wanted to be in a video or to have a similar life experience. I wanted to feel hands and mouths on my dick. I was realising that my cross dressing was only stimulation and foreplay to sex itself. I had by then realised I was bi-sexual. I wanted to make another dick shoot its' hot sticky cum over me or inside me. It was becoming a need.

I now had a deep desire to suck dick and have a load shoot in my mouth. It was becoming an obsession to have company when dressed, to be appreciated for what I was, and to have satisfying sex whilst I was dressed.

I did have girlfriends at that phase of my life. One was called Jackie. She was a nice looking 23 year old teacher. She had long dark hair, nice face and a figure to die for with spectacular legs which she was proud to show off by always wearing short skirts. I cannot ever remember seeing her wear trousers.

Jackie was great company and had a good sense of fun and humour. We went out on many dates and would always end our evenings locked in each other's arms kissing. She had deep green eyes and full sensual lips and her kisses themselves were a turn on. They were soft and damp yet could be firm and erotic as our lips embraced. Our tongues wrestled together in time with each other.

As we kissed I caressed her firm tits and could feel her nipples hardening. I would slip my hand inside her blouse or jumper and seek out her nipples. She loved to wear lace bras which of course unknown to Jackie I could relate to. Her nipples were so sensitive that she could orgasm just by having them tweaked, pinched and her tits lovingly caressed.

As we kissed and embraced I would softly stroke her legs through her hosiery which she loved and again I could fully appreciate how it felt. She said more than once how I knew exactly how to stroke her to get her really horny. Of course I knew just how lightly to stroke and caress utilising the sensual fabric to maximise its' effect. She loved my touch nearly as much as I enjoyed stroking her lingerie and hosiery.

She enjoyed me stroking her knees but especially behind them. I would work my way around to front and then up the silky thigh firstly up the outside and then to where it is most sensitive, the inner thigh, barely touching her there, yet just enough, would have her writhing wanting more. I knew just when to move in. I worked my way towards her pussy and used my nails to lightly scratch the already damp gusset between her legs.

Gradually I intensified my touch pressing more firmly as she lightly sighed. I loved the feel and how I was making her feel but I was jealous of it at the same time. I wanted to be on the other end of her ecstatic sensations. I would press more firmly and rub her opened pussy lips through her sexy panties making me harder and her so much wetter.

Once she was fully aroused I slipped my hand inside her panties which would leave us both breathless with desire. I expertly worked her clitty until she climaxed. I loved masturbating her this way and judging by how hot and wet she was and the fact that I could make her cum, she did as well.

The only thing was she was reluctant to get my dick out and do the same for me. This took its' toll on me. I was getting increasingly frustrated. She would cup her hands and grope my dick and balls simultaneously which was nice but I wanted more. I needed to cum. I wanted to fuck her lovely hot wet cunt. At very least she could have used her hand to wank me off. Very often I would go home and slip in to some sexy sensual lingerie and jerk myself off cumming loads thinking of Jackie's wet pussy in her soaking wet panties.

I had been denied too many times any form of sexual relief. She always made an excuse not to masturbate me let alone fuck me. At her home she was scared her parents would discover us in her home as she still lived with them. In the car she said I would make a mess if I came. That is exactly what I wanted, indeed needed! I tried unzipping myself one night and placing her hand on my dick to be left in no uncertain terms it was not going to happen.

When I asked if we could go to my flat or find a place to go and make love the answer was a definite no. This is where my imagination took over.

One evening when getting dressed to meet her I put on a pair of most delightfully sensual embroidered satin tanga style panties with lace side panels. Over these I then put on my most sheer tights. I was already aroused and the feel was making me want to jerk off there and then. However, I resisted relieving myself, although it took a lot of willpower. I finished dressing and with a semi erect dick went off to meet Jackie.

After a pleasant social evening we ended up as usual kissing and groping in the back seat of my car. I began as always massaging her tits then with my hand up her skirt started teasing and pleasing her thighs and pussy the way I knew she liked. At the same time she was gripping then rubbing my legs which were extremely sensual. Little did she realise why.

It was the first time I had been touched by anyone through female clothing. It felt tremendously horny. I was longing to have my dick inside her wet pussy. I reached for her hand and placed it over my stiffening dick. She commented on how aroused I was. If only you knew I thought. She cupped my balls and worked my dick gently through my outer clothing.

The sensations through my tights and panties had me squirming with pleasure. I had my hand inside her panties and continued to work her clitty. This was wonderful a moment, to be another milestone in my life. I got harder and harder as I got lost in the moment.

Shortly after she climaxed I shot my load filling my panties with hot sticky cum. Upon returning home and cleaning up I put on a black satin nightie with matching satin panties and finished the job off as I jerked myself off to a great climax watching my favourite porn.

I was getting frustrated not having a fulfilling sex life and beginning to think it was time to move on and maybe bring an end to our relationship when things took an unexpected turn.

We were to go out as a foursome with Jackie's friends Shelly and Mark. I had not met Mark before but had seen Shelly on a couple of occasions. We met up in a bar where there were plenty of drinks consumed and plenty of laughter.

Mark was a fit guy in every sense of the word. He was good looking, over six foot and one big pack of muscles. We were all getting on really well and becoming well on the way to being drunk.

Shelly suggested a game of truth or dare with the forfeit being to drink yet another alcoholic drink if you declined to do what was asked of you or to answer the question. This was great fun being set tasks or questions by others. The idea is to be truthful about a question you'd rather not answer or to be dared to do something you'd rather not do. We took turns in asking the deeds rotating around the others in turn. Some were simple, some embarrassing and some amusing.

We became quite noisy even more so as we became more influenced by alcohol. Eventually we were asked to be less noisy or leave. We chose to leave.

In high spirits fuelled by drink we went to Shelly's house which was only a short walk away. Once at her home we settled in to her lounge where she poured us all more drinks. It was suggested we continued playing truth or dare but after a while it became just a game of dare. I influenced the direction of the game by asking the girls to kiss. They did very briefly to which I said it wasn't good enough so they responded with a full blooded hot and horny long sensual one with mouths open and looked to include tongues too.

It was so hot watching them as their hands wandered too like lovers do. They appeared to be enjoying themselves. It didn't appear unnatural for them. We fellas were then dared to kiss but we refused so had to pay a penalty of downing a glass of whisky in one go.

Next the girls were dared to caress each other's breasts which they seemed to do only too willingly. This was getting hot. The girls then dared us to place our hands over the other guy's dick. Mark looked at me questioningly. I was up for it. He carefully placed his hands over my dick and I did the same to his.

I was already getting horny and as I touched his, which I could tell was so much bigger than mine, I gave it a gentle loving squeeze and as soon as his hand touched mine I became more aroused, I began to get hard. This has gone too far mark said. I've had enough of this stupid game and got up and walked out

slamming the door accusing me of being gay.

So I asked," Where does that leave the three of us?"

Shelly said that the night was yet but young let's have another drink. Do you mind if it is a coffee I asked with which she went and made the three of us an instant. We chatted as we drank it and the conversation inevitably turned to sex along the lines of our truth or dare game. We were all in good spirits and quite open in what we were saying.

What did I like sexually Shelly asked. Well, that was a loaded question! I answered, still fuelled with drink that my immediate goal was to fuck Jackie. She was amazed that we had never got round to it. I asked Jackie the same question but never really got a reply. In answer to the same question Shelly admitted to being bi-sexual.

"That doesn't surprise me" I said "you appeared to be enjoying yourself kissing and groping with Jackie earlier."

How about you she asked, "Have you any fantasies?"

Why not, I thought so what go for it. Actually I have always loved porn when two women get it on together but I have a more of a kinky personal fantasy. I love to look at women in their underwear and I don't know why but I want to experience wearing lingerie. (I didn't dare say I had a stash already and knew what it was like to wear it).

With that another door opened. Shelly lifted her skirt quite brazenly and asked if I liked her panties. They were pink and shiny so I guessed they were satin.

"Oh yes"I said "they are lovely." With that she removed her blouse revealing a matching cami top.

"How about that?" she asked.

"Oh that too. You look lovely" I answered "as does what you're wearing."

I asked what Jackie was wearing not expecting much response. She surprised me by slowly unbuttoned her top to reveal a white lace bra. I asked her if she was wearing matching panties. She surprised me even further when she removed her skirt to show a matching white lace thong. Oh I was getting so turned on.

This was a side to Jackie I had not yet seen. By now both Shelly and Jackie were just in their lingerie. It was such a scene for a lingerie loving cross dresser to take in.

"How much do you like my panties?" asked Shelly.

"Very much." I answered a bit shyly.

Surprisingly she then asked "Would you like to wear them?"

Of course my answer was yes!

"Then you will have to take them off me but first you must undress." Shelly responded.

I wasn't expecting this when we went out tonight but what an evening it was turning out to be. My clothes came off in only a few seconds displaying my semi-erect dick.

"Come on then" she said.

Over I went and knelt down in front of her while she raised her beautiful butt so I could remove her panties more easily. I was amazed at her lovely shaved pussy. I had never been that close to one without hair before, in itself it was enough to turn me on.

Jackie was giggling at the prospect of me in lingerie but I was determined to go through with the chance I had been offered.

"Put them on." Shelly said.

I needed no further encouragement. As I did my dick exploded in to life, as it always did, making it difficult to put it inside the beautiful damp pink satin panties.

"Oh my, Oh my" said Shelly "You really do like that don't you? Now sit back down and we'll put on a show but you must not touch your dick at all or else I want my panties back." She said.

First though she threw me her matching cami top which I pulled on immediately.

Sitting back I felt very horny being given my very own private lesbian sex show dressed as I was.

They were already kissing and caressing each other forgetting I was even there. They were so hot and horny. Jackie's bra came off and for the first time I saw her lovely tits. They were lost in the moment sucking each other's nipples and touching each other all over their bodies.

My erection was straining to escape being encased in their wonderful sexy damp satin prison. I felt so sensually aroused in her panties and top. So many times I had worn lingerie but never in company and never in such a horny environment. I ran my hands all over my chest caressing myself through Shelly's satin top but didn't rub my dick at all.

It was Jackie who first reached for her friend's pussy. She cupped it and slowly caressed the outer lips initially and then found Shelly's clitty circling it making her moan with pleasure. Hell if this carried on I was going to cum without touching my dick! Shelly followed suit and started masturbating Jackie. I knew just how that felt having done it so many times for her. Jackie looked over at me, smiled and winked.

My god I was so horny watching this lovely display of lesbianism. I thought I had died and gone to heaven! They were both so wet now. I could hear how much by the slushing sounds and see it on their fingers. I wanted to be involved and my dick needed to cum. They were really going for it exploring each other with hungry horny hands knowing just how to please each other.

Jackie looked over to me and said "Are you as good with your tongue as you are with your finger?"

"I'd love you to find out I answered". So with that, not needing further invitation I went over to join them.

I have to be honest I felt embarrassed dressed as I was and just a little intimidated being with two beautiful naked women. I kissed Jackie first thanking her for asking me to join in. As I did so I felt a hand caressing my dick over the panties. I turned to Shelly who had a wicked knowing smile on her face. She asked me if it felt good to which I replied so absolutely wonderful you wouldn't believe. I kissed her with all the passion I could muster loving her tits and pinching her nipples.

I turned to Jackie who was busy rubbing her clitty as fast as she could. I could not believe how truly an erotically lovely sexual experience this was. So much was going on.

I removed Jackie's hand replacing it with my own and continued her masturbation for her just the way I knew she liked. I tried to both please yet tease at the same time. As Shelly continued caressing me through her panties I reached for her pussy. Now I had one in each hand. I had gone to heaven!!

Both girls were now so horny, breathless and moaning softly. They kissed again and played with each other's tits so wonderfully. I could feel my dick throbbing and dribbling in to the panties now and was fearful of shooting a load as I had before when Jackie didn't know I was wearing my panties. Shelly asked me to lie on my back. No sooner had I done so that Jackie straddled my face. "Fucking eat me" she cried.

How can a guy refuse? I licked and sucked and tasted as much as greedily as I could. I had been waiting for this moment with her for so long, it was wonderful. I licked her clitty putting what I hoped was the right amount of pressure on it. I sucked her inner lips and tugged them gently a combination of which she was obviously enjoying.

I felt my dick experiencing a new sensation, Shelly was sucking it, and at the same time she had a finger in my sissy pussy. How I loved the joint sensations. Jackie was rubbing her dripping wet cunt all over my face now using it to masturbate. She ground it in to my face and on and off was frigging her clitty.

I couldn't hold out any longer and I shot my load in Shelly's mouth. Oh you bad sissy boy she said and but I haven't finished with you yet. It doesn't matter I said I'll soon get hard again in your company and I can cum again soon.

I put my limp dick back in my panties and moved over to enjoy Shelly's pussy. Firstly I simply stroked around it both tenderly and lovingly enjoying the fact it was shaven then moved in towards her labia and after a while centred on her clitty. It had already experienced plenty of attention but I was going to make sure it would get plenty more. I made her lay on her back and I spread her legs widely giving me a heavenly view.

It was then I heard a buzzing sound and turning towards it saw Jackie using a vibrator on herself. That in itself was a sexy sight. I was both watching her and enjoying Shelly's pussy simultaneously. I put one finger in and kept the pressure on her clitty with my rotating thumb. Then I put in a second and then a third all the time working her clitty. As I did so I saw Jackie insert the long slim silver vibrator all the way inside herself.