My First Day Into Womanhood

We were with friends playing a friendly game of cards when after a few drinks things started getting nasty. My wife and her friend wanted to up the anti by indicating that whoever got the lowest hand in the next round would have to portray themselves as a female for 30 days. Not just in female attire but also in a day in the life as a female. We all laughed and not really taking it too seriously we all agreed. Well as luck would have it I was the one with the lowest hand, and my wife wasted no time in explaining the rules to pay back my debt.

She explained that I would have to keep clean shaven from head to toe, but that I could leave a little « V » shape patch of hair above my penis. She explained that it would give the impression of a vagina. She then told me that I would keep up with the chores (laundry, cooking, grocery shopping) etc . She would move out of our place and go live with her friend this way I would live alone but must keep in character at all times. I would have to carry out all requests made by her and anyone else that wanted my services as long as they did not put me in any life threatening situations. I would not be a slave but basically must act like a real woman in every aspect. I hesitated at first but found myself quite aroused with the unknown possibilities that would confront me in the coming weeks.

So the next morning I was awaken at 6am by my wife and asked to take a bath and shave as indicated last night. While I was doing this she packed her bags and told me that we would go shopping for my new cloths and essentials. We went to a shopping mall nearby and started with Victoria secrets. There I purchased Brazilian thongs (black, blue, red, green, pink), which as my wife explained were wider than ordinary thongs for mor support without taking away the sexy look. I then got bra’s to match and 2 corsets. I was told to get only stockings giving a tastier look and feel to my ensemble.

Next we went to numerous female clothing shops to purchase mainly skirts that showed quite a bit of leg about 4 inches above the knee, open back heels 3`` , blouses, i spaghetti strap dress etc. I then had to go a speciality shop for wigs and makeup where I bought a black, and auburn wig one and my wife helped me with the makeup that went pretty good for my skin tone.

Once home my wife went through all the purchases to make sure that I knew how to wear them and when and how I should place my makeup without looking like a real slut. Before she left she asked me to get into something that I liked , so I selected a white knitted short sleeve sweater with a black spandex skirt that was quite short and I only then noticed that it also had a 3 inch slit along my left thigh. I didn’t want to wear any stockings because it was a hot day but did put on my green Brazilian thong’s. To finish my ensemble I put on my sandals with a 2 inch heel. My wife was quite surprised at how quickly I got dressed and complemented me. She told me to take care and that I was on my own, but just before leaving she said your first mission is to encounter people that i had never encountered and go to a club or bar that I was not familiar with. This I had to do this evening after I had cooked supper for myself.

From the time that I started to boil my water for my pasta till my final makeup touches I felt my penis getting wet and sure enough got whiffs of pre-cum scent. The problem was keeping my hardness hidden, so i decided to manually take care of the situation and 5 minutes later ejaculated to satisfaction. Once I was presentable I took my first step out of the house and immediately felt the cool evening breeze through my legs and on my mid area since the fabric was quite thin. I was surprised that I felt comfortable walking and was happy that my wife took the time to make me practice in heels. I then waved down a cabby trying to see if I would pass my first test . Where to ma’am, he asked as he looked at my breasts, well my latex breasts that we purchased at a sex shop earlier that morning. I was relieved that his reaction was genuine, meaning he would of fucked me on the spot if I let him.

Not knowing where to go I asked him to drop me off in the middle of down town and I would just walk around and decide then. Once I paid my fare I was surprised how I automatically without thinking lowered my skirt like any woman would once coming out of a sitting position, was I getting that at ease in my temp. lifestyle? I walked slowly and I was still getting my scent filling my nostrils, as my panty’s were getting quite wet, being mainly of lace they did little to absorb my on flowing pre-cum.

I came up to a club that I never frequented so decided to give it a try, as I walked in the door man stated the cover charge and guided me to a stool near the edge of the bar. He was a black man about 6’2’’ I would say 225lbs but good looking and great smile, I just stopped what was I becoming I never even considered another man and now I was noticing their built?? My cock was even starting to plump up again but I fixed the problem but gently tucking it back deep practically sitting on it. This is where the Brazilian thong’s came in handy their wider coverage gave me that extra support. I guess it helps to that my cock fully erect is only 6’’ taking up less area.

I ordered a drink and just started getting at ease when some came from behind me . ``Do not turn around you male slut’’, my whole body went into a sweat, shit I was found out. Ok I replied in my normal voice, in a deep voice he demanded that since I like dressing the part that I should be complete and sound the part as well. Not wanting to dispute I replied in the most femme voice that I could imitate and by his momentary silence knew that he approved. He then handed me glasses that were so black that I couldn’t see a thing before me. He turned the stool around with great ease and made me stand. As I reached out for support I quickly noticed his big structured body . He placed my arm under his saying that it would be a pleasure that I would join him . My heart raced to the point that I had difficulty breathing and felt very wet between my ass, my pre-cum must of coated my rear as I tucked it back earlier.

I noticed that we had left the club as the cool air blew between my legs, I asked gently where we were going and he replied since I enjoyed being a male slut that he would treat me no less. Now I was not sure how to feel should I run, scream, even though I was in this dilemma my body was reacting differently. It was horny and wanted to be satisfied.

‘’ We are going for a ride in my limo where all your questions and needs will be answered’’, as if he had read my mind. Moments later I was gently guided in the back seat of the limo and was asked to keep my glasses on. I almost preferred it not wanting to see what i was about to get into. I felt cool air above me so I suspected that the limo had a sun roof which was soothing because I was really getting hot. I then heard a zipper sound and clothing being handled before he asked me to position myself over his pelvic area with my back towards him . I naturally had to spread my legs wide enough and in doing so felt my skirt rise practically to my waist. ‘’MMmm, I like your thong and your scent is very strong my dear , I see that you body wants to play, ha,ha,ha’’ His laugh sounded nasty but i swear I felt more pre-cum escape my cock head and soak my green thong. I then felt my thong being moved aside till my ass was completely exposed and immediately followed by his big hands on my hips pulling me down. ‘’Wait’’, I said in my high pitched voice , are you protected. There was silence and in that moment I told myself what the hell am I thinking , do you think this guy gives a damn about protection. ‘’I see that you are not new to this’’, I should of left it there but I answered ‘’no it’s my first time dressed this way and with a man’’, trying to impress him . ‘’ Well my little male pussy let me give your virgin rear a night it will not forget’’.

He noticed that my ass was well greased in my own pre-cum , ‘’I see that you are well coated honey may I add to your wetness’’. Before I could respond I felt his cock head slowly part my outer ass cheeks and slide without end for what I thought was the biggest fuck’n cock in the world. He then stopped when he noticed that my moans turned to cries of agony. ‘’Slowly my virgin slut relax do not move let your inner muscles extend themselves and hug my black cock’’. Shit I thought now I know why he’s so big, and he noticed my reaction when he replied ‘’ Don’t worry my white male slut your my pussy now, no one else will fuck your ass but me’’ He then told me to slowly go up and down his long cock, I thought my inner tubing would come out as well.

After a few moments my moans replaced my grunts and he to noticed that my anal muscles were quite relaxed as I felt him inch further in with each down motion. Fuck yes I heard myself say as my body automatically quickened the pace. For no reason the car then stopped and both doors on either side of the limo opened. Two other men could be heard and these two really sounded black , one with a French accent while the other had a Jamaican British tone. Both men seemed to just watch as my ass hole was put to work again letting the long fat cock continue it’s depth, that’s when I heard two more zipper sounds . The French man moved in front of me as he sat on the opposite seats, ‘’Carl, let this male bitch bend towards me, I have a question to ask him, sorry the lady,ha,ha,ha,ha, they all joined as their laughter turned sexually nasty . As Carl pushed me forward his cock moved out about 2 inches but he quickly moved lower down his seat and regained any lost depth. Fuck it felt good,, when I was so close to the French man I could smell his thick muscky scent.

“ I would like to know have you ever had a cock in your mouth’’, no I replied. So I will guide you then just remember to keep swallowing or you will gage’’ With my dry mouth open since Carl began to enter me I let out a semi hum,hum showing my understanding. His right hand held the back of my neck as he guided his cock head into my open mouth. I had to open a little more as it was very round, so much so that i was concerned that my teeth would cut into his skin as it continued it’s inward motion. Almost instantly I felt his left hand that held his cock push forward letting a thick stream of pre-cum hit the back of my throat, I quickly swallowed but had to continue swallowing for his pre-cum seemed to just sit there.

So I felt myself moving forward again as Carl removed his cock making the French cock head rib up against the back of my throat, and that’s when his cock swelled up and shot so much cum in my mouth that I was only able to swallow half while the rest dripped along the edges of my mouth. He then took out his cock from my mouth and proceeded to ejaculate on my face. He removed my glasses as I felt his thick warm cum on my forehead, nose, cheeks , eyes. I then felt my ass being entered again and seconds later when the cock was at its deepest warm feeling of wetness coated my rear hole as he continued to pump me with deep strokes. While this was happening the black French man used his cock to slide the cum on my face towards my open mouth as I let my tongue lick it up and swallow. Carl then slipped out of my ass as I felt cool air around my opening. I would of given anything to see how my hole looked like .

Then the Jamaican slide into Carl’s place with his hands on my hips he just jammed his whole cock in one motion. I screamed like a woman as my face was in the lap of the French man. He pumped me very fast and hard too hard for my liking but I wasn’t in any position to argue, so I just grunted with every forward motion, I had tears hoping that he would not damage my insides. Please stop, I said I can’t anymore it hurts, please. Then I heard Carl, James give it a rest man you’re hurt’n the pussy. It paid off as James quickly slowed down and as he did his cock really swelled up and my rear love hole was given another does of warm thick cum.

I must of past out because when I awoke I was still in the limo , alone in front of the club, the driver turned towards me and ask where I would like to be dropped off. I awkwardly sat up felling sore in my lower back and lower tummy. I then took out my mini mirror from my purse and looked at myself, not back I thought. I then told the driver where he could drop me off and as he drove I looked into space wondering what a good fuck I just had……

To be continued…….