This is a true story, I have only changed the names and the location so as to prevent any embarassing identification of the people concerned.
It was earlier this year (2006) . I was a fairly normal 18 year old boy. Fairly normal I say because I am only 5'6" tall with small hands and feet, but wiry and strong for my size so I played scrum half at rugby and was accepted as one of the lads.
Sarah is a good friend of mine. We met at school on the first day when we were nearly 5 years old. So 13 years, lucky or unlucky, you decide later. We were really more like brother and sister. Then one day she said " hey you know I have been going out with David for a couple of years now." I replied " Yea, he's a really nice bloke and treats you well. You seem very happy." " yes we are" she said. " In fact, he has asked me to marry him and I said yes." "That's great news" I said. "Hoped you'd say that" she grinned.
"So when's the big day ?". "Three weeks time. We're getting married in the village church at Cannington." "Lovely I said. But not much notice ! "
"I wanted you to have not much time to think about what I am going to ask you . He's got a big family and lots of friends so my side will be outnumbered at the wedding." she said. " Sarah, that doesn't matter and I'll be there. " I replied. "I know that" said Sarah, "and it's important to me that you are there." "Great" I said " You know I am always there for you. "
"I want it to be obvious that you are there on my side and not just one of the groom's men friends. If you dress like them it will be difficult to tell." she said. "So I have a great favour to ask of you." "Ask away" I said.
"I want you to be one of my bridesmaids !! "
I stared at her open mouthed. "A bridesmaid ?" "Will you do that for me ?" she said "I know it's a lot to ask." My mind was in a whirl. " It certainly is a lot to ask." I said. At the same time I was strangely excited for some reason. " But why can't I just wear a suit like the other guys ?"
" As I said, I need you to be obviously on my side of the celebration." she replied. " I will understand if you say no, but I will be really disappointed."
I thought hard. " But what would you want me to wear ?" I said "Maybe a shirt in the same material as the other bridesmaids are wearing ?"
"No I want you to dress identically to the other bridesmaids."
"But I will be a laughing stock, looking like a young man in a dress ! "
"Believe me she said, that is not true. In fact you will make a stunning girl I am sure if you let me work on you. "
"You really want this don't you ?" "Yes" she said "You are my best friend."
"I am very nervous about it but I know you wouldn't make me into a fool. OK, if you really want it I'll do my best." "Oh I knew you would, you are such a good friend ! It will be a great day believe me."
"So what do I do now ?"
"The other bridesmaids and I are meeting on Tuesday evening to sort out what to wear. Can you be there ?"
"OK, I said" with a mixture of reluctance and yet some unfathomable excitement.
Tuesday evening arrived. I turned up at Sarah's house and she greeted me at the door.
"Come in , the others are here and they are so looking forward to you joining them."
I went into the main room and there were four girls there. Two were girlfriends of Sarah's from school days and the same age as me and they of course knew me. The other two were Sarah's 14 year old twin neices. They all greeted me as one of them.
"I am very nervous about this " I said. They all told me not to worry. They would look after me and they were so impressed that I would do this for a friend. "Not many men are brave enough to do what you are doing" said Jane, one of the schoolfriends. The others all agreed.
"Ok lets get on " said Sarah. "The most important thing is the dresses."
As she said this it finally sunk in what I had let myself in for. The next thing I knew I was being measured. "Good, a pretty standard size 12" said Sarah. "And only size 6 shoes" said Jane.
"So what kind of dresses do you want for us ?" said Angela, the other 18 year old ? " I have found some lovely ones on the Internet" said Sarah, "On a site called Girls of Elegance." With that she went over to her PC and brought the site up on the monitor. "Here we are, satin dresses in the style of a 50's prom dress. With matching satin stole."
My mouth dropped open. The dresses were gorgeous but so girly. Nothing covering the shoulders , the dresses were flared and came down to knee length with a small belt at the waist.
"Oh how lovely" chorused the other girls. "They will be so nice."
"What colour would you like?" said Sarah. The girls chatted amongst themselves and then unanimously chose the pink !
"Great choice" said Sarah, "With matching 3 inch heels, satin lingerie and stockings with just a touch of tan to make your legs look great."
By this time I was in shock.
"Ok so only two and a half weeks to go" said Sarah. "I will order the dresses and shoes etc. and book the beauty salon for the morning."
"Beauty salon ? " I said.
Sarah grinned. "Don't worry, just your hair done in a female page boy style, some lovely makeup and some false french manicure nails. I have managed to find some screw on earrings that match the ones that the other girls are wearing so I'll let you off getting your ears pierced ! "
I was completely in a daze and stayed that way until the wedding day.
Sarah wouldn't let me see the clothes until the day. I turned up at the salon having spent most of the two hours since getting out of bed on the toilet. I was so nervous.
They greeted me at the salon and said that the car was parked out the back so that I could get to Sarahs house without looking strange all made up but in my male clothes.
Jane took me to one side and whispered. "We aren't going to let you see yourself in a mirror until you are all made up and dressed back at Sarah's house so that we don't spoil the illusion. I hope you don't mind me being personal , but if you get excited by all this might I suggest that you go to the bathroom and masturbate before you get the dress on. Don't want any stains do we ?" She winked and walked away. I almost fainted.
They got to work on me.
First they told me to shower and gave me some cream that rid me of the small amount of body hair I had. My head of hair is quite strong and was reasonably long for a man. The hairdresser trimmed and reshaped it then washed it and blow dried it. Apparently it was now in a feminine page boy style but they wouldn't let me see.
I was grateful that by now most of the attention was on Sarah, after all she was the bride and she looked great.
While a beautician did my face, which seemed to take ages, another stuck on false french manicure nails. I looked down at the only thing I could see that they had done to me and my hands looked so feminine. A tremor ran through my body.
With the last touch being my lipstick, which would apparently need touching up later, they attached my earrings and we were off in the car to Sarah's house. The twin neices followed behind. When we got there I thought all the others looked fantastic. The two older bridesmaids looked beautiful and I really fancied them both. The twins looked really cute. Sarah of course looked radiant.
"OK" said Sarah "I will see you all at the church. Jane and Angela, you are in the bedroom on the right and you twins are in the next one along."
She looked at me. "I'll have to call you something different for today. I think Rose is a good name. I think you will look like a Rose in your dress."
At that point I nearly said that I couldn't go through with it but she ushered me into the bedroom on the left and said "All your clothes and your bouquet are in here. Once you have the underwear on call out and my mother will come in to help you with the dress and shoes."
I was like a robot. I couldn't focus. I automatically got undressed and looked at the lingerie on the bed. There wasn't a bra for me to struggle with as the dress was such that a bra would show apparently. Sarah had said that her mother had sewn some padding into the cups and that she would put in some small inserts when she helped me on with the dress. I put the lovely garter belt around my waist and clipped it together. The clips hung down my legs. I rolled up one sheer stockings in my hands as I had been shown and pulled it up my hairless leg. It felt great. I clipped it on to the garter belt and repeated with the other stocking. I pulled the satin panties on after this as I had been told to do. By this time I was shaking uncontrollably and suddenly had to rush into the bathroom and pulled down my panties just in time as I spurted loads of cum without touching myself. I had to sit down as my legs had gone weak. I cleaned myself up and pulled up my panties again. I went to the bedroom door and in a weak voice callled out to Sarah's mother that I was ready. She came into the room and could see that I was so nervous and embarassed for her to see me like that. "Don't worry dear. I am so proud and grateful that you are doing this for my Sarah. Now let's get your dress on. "
I stood up and she took the lovely dress off its hanger. I stepped into the dress and she pulled it up my body and zipped it up. I felt so amazing. The feel of the dress against my stockings made me feel so feminine and vulnerable. "Now the shoes" she said. The matching 3 inch heels were slipped onto my feet and the buckles done up. "Stand up beautiful" she said. I stood up and the heels made me stand in a much more feminine way immediately. She gave me my bouquet and pulled the cover off the mirror. "There you are my beautiful, a real Rose"
I looked at myself and staggered a bit. This couldn't be me. "You look as good as any of the other bridesmaids, Rose. Only my Sarah, the bride, looks more beautiful." Then the words that really made me nearly freak out. "Looking that good you'll have to be careful when you are dancing with the best man or the other guys ! "
I felt really strange and vulnerable and yet excited as the four of us got into the wedding car. I clutched my bouquet and smoothed my dress under me as I sat down. The heels had made me walk in a feminine manner to get to the car.
The car arrived at the church and we had to walk through the gathered guests and wait in the entrance for the bride. They all said how beautiful we looked as they passed us to sit down as the bride was due to arrive. The main car turned up and Sarah, looking beautiful, walked up the path on her father's arm. We all turned and followed her down the aisle as the organ played. I was glad that they were all looking at the bride as my heels clicked and my lovely dress swished against my stockinged legs.
The service went wonderfully but I found I was so nervous that I couldn't sing the hymns and my mouth was dry. There was a slight breeze from the open church door which went up my dress and caressed my smooth legs and panties.
Soon the service was over and we started to follow the bride and groom from the church. One of the smartly dressed young men from the groom's side offered me his arm and we walked out together. The photographs seemed to take for ever and my mind was in quite a daze as several people spoke to me but I really didn't take it all in.
We got back into the cars and went of to the hall for the reception. When we arrived I really needed to go and relieve myself. Jane grabbed my arm as I was about to enter the gents and gently steered me into the ladies room. She suggested I freshen my lipstick and I felt so girly seeing my manicured nails on the lipstick as I applied it freshly to my lips.
We sat and ate our meal and then the speeches came. Being a strong independant woman, Sarah insisted on making a speech as well as her husband. I was sitting quietly, trying to be anonymous and consuming probably too much wine. Suddenly I heard her say that she thought all of her bridesmaids looked great but that she would especially like to thank her best friend Rose who had been with her for so many years and looked so good in her dress. I nearly fainted.
Sarah and her husband got up and started to dance the first dance to a lovely slow love song. Then five young men who had been asked to do so, came over to the five bridesmaids and took us out onto the dance floor. There was I all dressed up as a young woman, in the arms of a young man and having drunk maybe a little too much wine and trying hard to follow rather than lead.
The dancing went on for a long time and I was asked to dance by a lot of men. One young man came up and asked if I wanted a drink. I said yes and he got me another glass of wine. As we chatted the bride and groom started to leave. Sarah threw her bouquet over her shoulder and Angela caught it. Suddenly I realised that I was disappointed that I hadn't caught it. I started to cry softly. The young man whose name was Steve asked me if I was alright. I said yes but that it had been a stressful day for me. He put his arm around my shoulders and led me outside into the garden for some fresh air. I wondered why I felt so at home with this situation. Where would my day end ?
We walked in the cool air down to the bottom of the garden and into a small grove of trees where there was a seat that loked out over the river. I suddenly realised that I felt good dressed like this and with Steve looking after me. We sat down and he told me that he knew my situation and that he thought I was great to do this for a friend. He then said that if he hadn't been told he would have thought that I was just a very beautiful young bridesmaid. I started to cry again and he held me close. Suddenly I looked at him and he kissed me. I realised that I really wanted this and that I might never get another chance. He apologised for kissing me and I told him that it was Ok I wanted it.
We kissed again and his hand started stroking my leg under my lovely satin dress. As his fingers found the garters at the top of my stockings I felt him tremble and I felt so good. My hand brushed his lap and I felt that he was big and hard. I knew we should not be doing this.
"Do you want me ?" I asked him and he said "Oh yes" "But you know I am not a real girl" I said. "No-one would guess unless you told them" he said. I thought how I had got into this and knew I had to just follow my feelings. "What do you want me to do ?" I asked. "Unzip me and take out my cock" he said. I unzipped him and pulled his big hard cock out of his pants. Here I was dressed in a lovely satin dress with my stockings pulling on my garters and I could see my small hand with its manicured nails wrapped around his hardness. He gently took hold of my head and steered it down into his lap. As I went down it just seemed natural that his cock slid between my lips and into my warm mouth. I felt so helpless yet good.
He moaned as he slid in and out of my mouth leaving lipstick traces on his manhood. I felt an orgasm building up inside of me and I hadn't even touched myself or been touched.
I wondered how I would react if he came in my mouth. I never found out because he gently pulled me to my feet and turned me around. He bent me over the seat and lifted my lovely satin dress. He pulled my panties aside and before I knew what he was doing he pushed his hard wet manhood gently bit by bit into my tight bottom. Soon I could feel his balls against me and knew he was all the way in. It felt so good. He started to pump in and out of me telling me how beautiful I was. I moaned and told him to make me his girl.
As a picture flashed into my mind of the moment Sarah had asked me to be her bridesmaid, Steve let out a cry and I felt his cum flood into me as he orgasmed. I knew it was meant to be.