This is a tale of pure fantasy, a story of the life of a boy blessed with a power. A masculine power hidden under the guise of women's clothes. It is about his struggle to find the answers and happiness in his life.

 

Lover In A Nightdress

by Jimrossi

 

To the best of my memory, I have always worn female clothes and have always been mocked for it by other boys. Yet the girls seemed drawn to me, thus I was drawn to them and spent many hours playing dress up. My mother instead of buying me action man always bought me Sindy and her accessories, yet this never seemed strange to me.

Let me tell something about my self, my name is Joseph, but this is often reduced to Jo. During my early years, which I have seen in photos, my hair was always long, I was always pictured in dresses, panties and tights. Many schools when I was young accepted this and punished the children who mocked me. Going through primary school, when 5 my mother always told whenever I would complain about seeing boys of my age in shorts would say 'Don't worry Honey, they're only jealous of you because you're special.' The boys taunts hurt me but my mothers saying kept me from crying, after all the girls would take me to one side and we would play skip rope as my skirt rose when I leaped.

At the age of 8 I entered junior school, now this was where the taunts really started and physical bullying began. My mother seeing me return home in torn school dress, Mary Jane shoes, upturned socks and hair in a mess would comfort. Her words of comfort did not work this time. How I wanted to be boy and dress like the other boys in school in shorts, shirt and trainers. So for a month, I was dressed as a normal boy, my attempts to fit in and play soccer were disastrous. They called me Sissy Jo and to play skip rope with the girls. However when I went to the girls, my previous only friends they also shunned me saying I looked silly in boy's clothes and walked away from me.

Friendless I decided to resume what made me happy. I walked home to be greeted by my worried mother. I forgot to tell you my father left when I was a few days old, never wanting to be a part of life. I was told from the start and now only need my mothers love for happiness, together were a strong team. We sat down over lunch, her in her nightdress, and me in my PJ's, she told me she only wanted me to be happy and that she would agree with what I chose. My mind racked with a thousand thoughts, the mocking of the boys, my failed attempt to conform with the boys when dressed in shorts, the shunning of the girls and the previous happiness playing skip rope when dressed in my skirts. My decision was made; I went upstairs, took out a silk nightie, removed the PJ's and placed the nightie on with matching panties. We agreed that it would be better if I went to an all girl school, how this would be achieved I did not know but somehow my mother arranged. The next Monday she drove me to St Margaret's School for Girls where I would pass every exam with flying colours.

The first morning I wore a cream training bra and panties set, why I needed a bra I did not know but I wore it to please mummy. A Cream school blouse, matching skirt and Mary Jane shoes. A satchel held my schoolbooks, my hair tied in bunches and a light make up. We entered the head mistress office that questioned us both. She asked why I wanted to join a girl's school when I was a boy. I replied the girls were nicer to me than the boys and the clothes I wore now made me happy. She seemed to accept it and I was announced in assembly I would join the classes. It was strange, that my penis always rose higher and higher when I was wearing silk panties and near the girls. Nobody said anything, at that age they accepted it, thus so did I.

At age 13 I was still in St Margaret's school for girls choosing my subjects. I chose home economics, business studies, Latin, French, Italian, German, Spanish along with the normal subjects everyone took. The Italian teacher could see I was finding it hard and offered to give me private lessons, but they were to be at her house off school premises. My penis was getting noticeable now when I got excited. And I got excited regularly especially when dressed in silk panties, which were given as gifts by the teachers, even the Head Mistress. Anyways, I went to the Italian teachers house, Mummy said I could stay the weekend so I did.

 

The teacher Miss Helene spent the first day teaching me grammar and conversation, often acting out scenes like an actress. This worked as I felt in character. She then told me that I was to play an 18-year-old man, who was being chatted up by a 25-year-old woman. Now I was 13 but this seemed okay, we had done this before. I wore a black cotton panties and bra (Still I did not need the bra but wore it as it seemed normal) black leggings, female trainers, and white blouse. And I was playing the part of an 18-year-old man, oh well it worked for us.

 

As she spoke of asking each other out, and the first date, she kissed me deeply as her hands rubbed my penis through the leggings to no reaction. Now I liked her but nothing rose. I felt no excitement. She seemed disappointed but carried on kissing me. The scene went something like this but in Italian:

Miss Helene: I want you to fuck me. Fuck me now.

Me: Take of your dress, panties and lie on the bed.

Miss Helene: Right lover come and do it now.

She lay on her bed naked as her hands stripped me as I lay next to her. Still she kissed me hard and still no reaction.

Finally in anger she told me to go to sleep, I did not know why she was angry, after all I had learned Italian and she had played her part well.

She checked through her draw for a pair of PJ's but found none so threw me a silk exquisite nightie to wear. I placed it on my body and became hard immediately. Miss Helene looked shocked and yet delighted, she jumped on the bed re starting the previous scene. Now her hands reached under the nightie caressing my hard penis, her face dropped under the material as she sucked me like a lollipop. She told me it was part of the scene so I let her do it. Next she whispered in between her sucking that I should caress her body as she twisted around so her face was on my mouth. On her orders, I sucked her vagina until she came three times, my hands caressing her breasts as she moaned. Quickly she spun around placing her vagina on my penis, riding me for 30 minutes, sweat came down her brow as I bucked into her as she asked. She looked very tired, the scene was very physical. She then asked me to go behind her as she directed my penis into her vagina and to enter her repeatedly. This I did for an hour changing into many positions until I spurted some liquid in her as she collapsed on the bed. She whispered, "Well Done. That was good but it needs practice. We'll try tomorrow".

And we did. Sure enough my Italian improved greatly.

As did my Spanish, German, Latin, and French where I also stayed the odd night with the teachers. My mother saw my rising grades and never once stopped me from visiting the teachers.

At age 15, I was invited to sleepovers, but never attended. Gifts from teachers of silk exquisite nightie arrived weekly, every female teacher invited me around to further continue my studies, and each brought a new nightie. I now had so many nighties I kept many around their houses just in case. Often they seemed disappointed when I did not become erect during a scene when wearing the nightie I wore the previous night.

At age 16, I started to attend parties and slept over some fellow girl student's houses, the girls I was a boy who dressed in women's clothes and accepted. They accepted it even more when they passed me a silk nightie and I become erect. That night we did homework as she called it under the guise of a scene. I stayed that night with the girl always. The word spread and I was invited more and more to homework sessions. The parents didn't seem to mind but found their daughters always more tired than before. My mother at the age of 13 took me into hospital where the doctors did some surgery on my testicles, I asked mummy after and she told me it was to protect me. When I got older I would be told the reason. Again I accepted this without complaint, mummy looked after me well and spoiled me rotten even though I spent only a few nights in my own bed.

I finished school at St Margaret's passing every course with straight A's. Soon I was to go to college to study art and filmmaking. The teachers each gave me their home phone numbers; some invited me to join them on holidays, of course mummy accepted so I spent a week with 10 teachers in exotic locations. Even though I had finished my studies, they still continued to practice my skills on the acting a scene principle. I did not care, for in my pink bikini I would spend the day by the pool or dressed in summer dress and sandals walk around the town. Often on my own as Miss or Helen (their first names) was too tired to leave the bed.

 

Those ten weeks I started to understand the power I had, women who had heard of my night studies from the teachers and students, offered to take me on holiday to further my education. Each one bought me a new outfit especially making sure there was a new silk or satin nightie to sleep in. Some people brought cotton nighties and became upset when I did not become aroused, the next night they made up for it with a luxurious nightie set for me to wear. One night, a woman, Sara I think her name was, I met her by the pool as Miss Helene was sleeping asked me to join her so I could practice my Italian with her. She had spoken to Miss Helene and seemed reluctant to accept my answer of no. Now mummy said always to help people if I could, so I finally accepted. That night I wore a pure silk/satin combination red nightie with matching stockings, underwear and high-heeled shoes. Before I stayed in her home, she took me out for a meal, dressed in new underwear and a flowing red dress with my hair in a braided ponytail at the back. Many men laughed at this teenager in women's dress dancing with this stunning woman, she fought back the men protecting me saying I was more man they would ever be. Now I liked this protection, I was used to this from the age of 13 and it seemed normal. As Mummy said they were jealous of me and I was special. At least my new friend thought so.

The meal was lovely, the wine nice but she was even nicer. I knew I liked her when she first kissed me whispering in me ear 'Its time to practice'. That night I placed in my new nightie, it felt luxurious to the touch, my body tingled in a way it had not done before. She whispered words of lust into my ear as her hands reached under the nightie to my new panties as I became hard, she gasped as her mouth swung around my penis as her vagina stopped at my mouth. For an hour she sucked me, later I was told it was a blowjob and 69er. These terms meant nothing to me; I only knew them as practice and study.

She oozed liquid many times. We started practice at 12 midnight and the next time I looked up after entering her was at 4.30 am when I finally came. She collapsed in a heap on the bed as I fell asleep. That night I slept arising at 10 am where I went down to the hotel pool where another beauty offered to teach me her dialect. Of course being nice I accepted.

I asked mummy after I came home from the final trip about the lessons I received, she passed me a book called the Karma Sutra. I read and re read this book. It showed of acts, which I had done. I knew now of the words to cum, making love, doggy style, anal and 69er. She also passed me other books called the 'Art of lovemaking'. I divulged all the information with relish and it made sense. The women were tired after orgasm, which was the liquid they oozed. The smiles on the women's faces spoke of true tiredness and satisfaction. I asked mummy why they did it, she told me that if I could make any woman happy like I did, I would be popular and it was my duty to do so. Again I accepted this without complaint.

 

My first day of college was not so great. I wore a short black leather mini skirt, black tights, heeled shoes, black silk underwear, blue blouse and jacket. Rucksack was filled with books, pens, I was all eager to learn. My long blonde hair was tied back because I was entering art class and did not want it to get messy. My first steps in the classroom were met by silence. They could see I was a teenager but dressed like I was made them stare nastily. It was not only the boys who were mean but also the girls who moved away from me when I took my seat. The male teacher entered staring at me like I was some king of freak. I spoke over mummy's words that I was special but I just wanted to cry. Usually girls were my friends, boys never did like me but girls always did. This was a culture shock to me and I did not like it.

 

Finally the class ended, nobody spoke to me so I sat there alone in the classroom, or at least I thought I was alone when suddenly a hand touched my shoulder saying 'Its okay to cry'. So I did. She introduced herself as Mary and she was the most beautiful blonde haired girl I had ever seen. My body tingled as she touched my hand, her hands wiping away the tears with her handkerchief. She looked at me telling me she would look after me. We talked for many hours, I told her about my holidays and the women who taught me things. She seemed shocked at first but laughed saying I must be very clever. The college was not designed for languages, being fluent in 5 languages stood me out from the crowd, so when a new girl joined, I was asked to befriend her. Out of necessity they would stay with me but always with a look of disdain. Thankfully they learned English and they left me to go back to Mary. Despite her beauty, Mary never had any dates, she was popular in college but after being with me they kept their distance from her. She was called names like 'Fag hag' but never retaliated.

 

Finally our friendship reached its point when ten girls and boys taunted us until we ran from college to her house. Her mother agreed to let us sleep over. I rang mummy who after speaking to Mary's Mum agreed.

That night Mary gave me her best nightie; it was part satin, part cotton. It was nice but not great. As we kissed, this time under no guise of lessons for I really wanted to kiss her, my penis rose, as did her glee. She caressed my penis, until she climbed on top of me riding me hard, then I remembered the books that told that women liked to be touched and experimenting was good. So I suggested we try different positions which after some reluctance she did. Finally after riding her doggy style I came inside her. We had started at 11 pm and now it was 12.30 midnight. She was exhausted. Her mother heard us making love and was surprised. Her bedroom was next to Mary's so she could hear the excitement. The next morning I awoke with Mary who could not walk straight, her legs seemed to ache. There was Mummy and Mary's Mum. Mummy sat me down as I straightened my nightie as Mary and her mother left the room.

"Now Jo, I know of last nights activities and of all the other nights for 3 years. What you have, what I have developed be it right or wrong is a curse and a blessing. As you have noticed, every time you wear a nightie you become erect and are able to keep it such for a long time. I know you have questions but those are your to work out, you have some answers already but you need to clarify them yourself. You have the ability to provide women with a great pleasure, which is a blessing, a responsibility for you to use wisely. However it is a curse as that great pleasure takes a lot out of women physically thus is why you may never find true happiness or love in a long-term partnership. Now Jo this is important so please pay attention. You have a great power. You must never tell of this to be selfish, your power is only drawn out by the discovery of the woman.

The surgery you had at 13 means you can never get any disease from having sex or make them pregnant, when you meet the one who will be your match then you position will be reversed and you will be able impregnate women. Until then you are safe from all diseases and worries. Once they know it is okay for you both to be selfish in your desires but be warned, a woman will only be able to cope with your power a few times and any more they will reject you. Be careful. Think before you act" Mummy said with a kind honesty.

She then left saying that if I wanted I could spend another night here. I surely did and would do so.

Mary's mum Julie was intrigued by the previous nights events, Mary was to go to her fathers for the night. She had explained that her parents were divorced so she split her time between the two. Her mum explained that her father would not accept me, a boy in girl's clothes so it was better for me to stay here with her. I agreed without question.

That day I had a lovely time with Julie, her buying clothes for college, some for Mary, some for me. Then whilst I ate my lunch in the café, she disappeared into a store bringing out a bag, which she told me, was a surprise. That night we discussed about the clothes I wore and my feeling s about them. I told her that I felt happier in them than in boy's clothes. We also discussed about normal matters as well. Soon it was time for bed. Since she did like to sleep alone and I was alone she suggested that we sleep in the same bed, her bed. Thinking on my mother's words or caution I agreed, as she seemed to desire happiness.

I stepped out of my short flowery summer dress, underwear as I had a shower; it was a hot day so she joined me. It was fun washing her. She was 35 years old but her looks belied her age.

She left first, leaving a towel for me, then as I left I saw this Anne Summers Satin nightie on the a hanger on with a note saying 'Jo, its for you'. When dry I placed it over my shoulders, as I became semi hard, I walked into the bedroom and she was in a matching nightie to me lying on the bed.

"Jo I heard you last night, I haven't had any happiness at night for a long time. Mary does not mind about this, she knows, she is young and is unable to cope with you. I would like to try and further your education" she whispered seductively.

How could I refuse that, she wanted happiness, I hope I could bring her some and she would add to my education. Upon her first kiss I was fully erect, she gasped upon lifting the nightie.

 

"Right lets take this nightie off then shall we," she demanded as her hands lifted it off my head. In a second I was flaccid and she was upset. For five minutes she sobbed until I came over with her asking me to put the nightie back on. I agreed and was instantly fully erect again. She then knew one part of my power.

I caressed her breasts as we kissed, she dropped down kissing me all over down to my penis, and the foreplay with lasted an hour and was the best I had felt. She came only once in that hour. For 5 minutes we rested as our hands caressed the others body, then lust hit her. Her hands reached for me to mount laying flat on the bed as she whined to be fucked. I do not like to use that word but that was what she begged for. I did indeed fuck her, with her on top, from behind, legs high in the air, even anally. We started at midnight and at 3 am I came in her mouth with her joyfully if not tiredly swallowing all. That night I slept in my new nightie, holding her who had collapsed exhaustedly with joy.

That morning, Julie hobbled down the stairs, the same condition her daughter had had and kissed me. She thanked me for the night saying she was no match. As mummy had said, it was a curse and a blessing. I now wondered if I did find true love, would she first be able to accept as a man in woman's clothes and if so would she able to last the rigours of the lovemaking. For the first time in my life I was scared, scared of the curse and power I gained. Julie saw this and hugged me. As she hugged me, Mary entered the room seeing me openly cry. Wondering why, I explained to both of them of my fears. They both sat down saying that fate would decide when I would meet Mrs Right and until then I could provide happiness to women everywhere. They both told that that was a good thing and I should be proud to have this power. They added that all the discrimination about my clothes and lifestyle would disappear when my goodness shone through, I would have to be happy in myself then this happiness would reach to others. Drying my eyes I showered, dressed in a new red skirt, blouse. Underneath was new silk underwear. My flaccid penis not showing through, only visible when erects. A case of two extremes. Either flaccid and wilted or powerfully erect. A curse it was indeed.

 

Back in college, Mary walked, I say walked but walked in happy pain to curious stares from all around. We walked in together, hand in hand smiling, me in in new skirt combo, and her in a matching one. Initially we got jeers but after lunch this changed, more girls came up to me, each trying to gain my attention. Now I was flattered by this but confused so went to see Mary. Mary explained that being with me made her happy and the girls tried to get more information out of her but couldn't. They in their curiosity wanted to know the secret. Now some of the girls were too pushy, demanding to know why Mary was happy now. Others being shy did not dare to speak. Others were themselves, some flirty, some honest. The pushy ones were rejected, this rejections causing them to call me names and go with the other boys but always with a deep regret. Out of all the girls, I joined for the night a brown haired slightly obese girl called June, June was not special looking but her eyes spoke of a desire for happiness. She never once suggested sex, hardly even talking at all,

 

It was Mary who gave her a wrapped parcel to give to me in the night; in the parcel was beautiful silk nightie, not too flashy, just a plain nightie. That night we made love for 90 minutes. She came like no one had before, being the fatty of the class made her lack self esteem, now although she had 'the walk' as it was called she felt confident.

Striding into class, June shined with confidence, some girls looked on in jealousy, others became wise to the fact that it depended on the girl who I was attracted to, not the looks. The girls flocked around her asking many questions on the nights events; the only answer that left her lips was 'I was being myself'. She spoke an honesty that underlined the truth, I admired honesty in people, if you were nasty or nice, as long as there was the honesty I was happy to accept you.

The next night I spent it with a stunning red head called Ruth who bought me a shimmery satin negligee, the negligee was beautiful but the intention was corrupted, we still made love but it lasted an hour.

 

A conceited girl called Lisa presented the next night the same nightie to me and I failed to become erect, she felt cheapened calling me a fag. Certain things were becoming clear, if the intention was honest, the nightwear as beautiful as they could afford and given in joy, I would be erect for many hours. If it were beautiful, but given in conceit or negativity I would either be flaccid or last an hour, which seemed to be my minimum. Also to inspire me the nightie had to be new or else my interest was zero.

The girls figured this out way before me, the next night a shy girl called Fiona brought me a cotton nightshirt, she passed to me in disgust but saying it was a gift given to her and that she was poor. She said she didn't know what to expect and was scared. I told her I also was scared and that whatever happened would take its cause. She told me openly she was a virgin and I asked her many times if she wanted to leave. She declined this saying it was what she wanted but still was scared and felt stupid for asking me. In a guise I asked her to help me practice my French, which she spoke fluently, this relaxed her and soon we matched together. For three and a half hours we made love, gently as she wanted then harder per her requests. She felt joy on every touch, and then after I came in her, she thanked me for the night before we fell to sleep. I in turn thanked her for the honesty and broke down saying I was cursed with this thing. She held me that night reassuring me that it will be used to spread happiness and I should enjoy it.

The next day in college, I noticed some of the men dressing in blouses or wearing less macho attire. With every girl doing 'The Walk', the men tried to experiment with their female side, some wore earrings hoping they would catch some of my power. All I can say to those men who were honest with their feelings were successful, those who tried to use it as a scam failed miserably. Over time the men spoke to men as a friend, first to get information, then just as friends talk. Some became very protective of me, teaching me martial arts. The gay community hounded me, telling I was in denial but I spoke to them openly saying that men did not interest me and that my lifestyle was my lifestyle. I was just being me. Some accepted it; some did not. Either way I gained more new friends than enemies. In time those who were against me felt liked outsiders and wished to join. It was strange to see bitchy women, straight jealous guys and the gay community talking and bitching about my power and me.

I am now 21, I run my own business along with Julie, Fiona and Mary. We run an open house, we teach people to be themselves. At first people came in jest, they left gaining nothing. Those who came with honest intentions realised their inner self. Women came baring gifts enjoying the night of passion with me, only to find a husband who also wore women's clothes. Men coming looking to explore themselves to find out their fetishes were not only shared by them. Meetings were held with each person explaining their goals. Some came in unsure of their sexuality leaving knowing and accepting if their gay, straight or bi. Julie, Fiona and Mary each had sex with the guests but only when it was mutually agreed, their honesty allowed the man or women to last longer. Their honesty and power spread to their bedfellows.

 

The business is a success. I am still bedding women nightly, still enjoying the honesty of lovemaking. Still I walk around in dresses and female clothes but now have the advantage of being accepted in the community. When we first opened, we deemed a brothel, but more and more people came and now accept our function. We have staff that work for a short period unable to last longer than 2 weeks. Sex is optional and not that important to our goal. We have helped married couples reconcile their differences just by telling them to be themselves. Our goal is honesty in others. No lives have been ruined.

I am still looking for the right woman to accept me as myself and who is able to control the power within my legs. On the wall in my bedroom is a 12-inch ruler above the bed. Women look at that in confusion only to be met with gasps of surprise when I become erect and then realise the ruler's significance.

  

  

  

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