PDA

View Full Version : (R Woody) Becoming a Woman



ianfook
05-03-2008, 09:34 AM
Becoming a Woman
author R Woody

This story started a couple of years ago, or should I say it all started 40 years ago when I was 13 years old. It seems I have always enjoyed dressing in women's clothes. I have been a closet cross dresser for most of
my life, starting with dressing in my mother's, sister's, aunts, friends, etc. underwear then my wife's and at any opportunity pinching other women's underwear when the opportunity arose, then wearing them under my
regular clothes. Recently I bought a video and a couple of books on cross-dressing on how to buy clothes, apply makeup, walk etc. These are my bible as how to act like a woman.

A couple of years ago I started chatting with other cross dressers on line and comparing stories and advice with these guys out there in cyber space. I then joined a men's personals chat line and talked with a lot of guys that were interested in meeting me so they could see me dressed up. This was scary as no one had ever seen me dressed in women's clothes, until I met Jeff.

This is where my story begins:

I meet Jeff on Lavalife. We talked and exchanged pictures for 2 months or so before we met. We talked about what we liked, wanted, what we would do the first time we met. It was very exciting fantasizing with each other. He would send me pictures of himself nude and with nice clothes, on he didn't dress in women's clothes he just liked seeing other men dressed up.

I sent him pictures of me dressed in women's clothes that I had bought over the years, some with me in nice underwear, and sexy tops and skirts. I had bought my self a excellent pair of silicone breasts from an online store a few months ago, that looked very real, and by this time I had a not bad collection of clothes, underwear and shoes.

The few months I talked with Jeff over the net we became very comfortable with each other. I travel a lot for my work so I arranged a trip close to the city that he lived in and we made plans for an afternoon to meet and get to know each other.

We met in a nice little bar not far from my suite hotel. I was a little late getting there and when I walked in their, were about 8 or 9 people around the place having a drink. I looked around and spotted Jeff immediately he looked just like his pictures he had sent me. He is 63 years old 6'2" about 250 pounds, not real fat just nice and big a bit of a belly, and a he is an extraordinarily fine looking man. He has salt and pepper hair trimmed nice and neat bald on top with just a wide fringe above his ears. In other words a very nice looking man that keeps himself well kept. He was dressed in a black suit, burgundy shirt and tie.

I walked over to him and said "hi Jeff I'm Richard." We shook hands and I sat down and ordered a drink. Jeff already had one going so we started with some small talk and we BS'ed for 3 or 4 drinks. Finally he said "we should go to your room and talk, as he couldn't wait to see me get dressed up for him." We finished our drinks, I went up to the bar paid our tab and Jeff and I left for my room.

It was busy out on the street and had started to rain while we were in the bar. Jeff had his umbrella with him so he put it up put his arm around my waist and pulled me closer to him so we could share it. as we walked back to my room he kept his arm around my waist as we walked, this got my heart racing a bit as it was extremely exhilarating to be walking down a busy street
being held by another man.

On the way to the hotel we stopped at a liquor store to get a couple of bottles of wine, as we were looking at the selection he put his arm around my waist again and held me close to him while we discussed what we liked
to drink and selected 3 bottles. This was also stimulating as I had never had another man be so affectionate to me in public before, he also gave me a
kiss on the cheek when nobody was looking. We paid for the wine and slowly walked to the hotel holding hands.

When we got to the room I poured us each a glass of wine and we sat on the couch, making small talk. After the first glass of wine I leaned over and kissed him on the cheek, and said "I need a few minutes to go get ready for you." He said "hurry, I don't know if I can wait much longer."

I got up and went into the bedroom and closed the door so he couldn't watch. I had put all my female underwear on before I gone to meet Jeff. I had put on my open butt garter belt and mauve coloured nylons, so all I
had to put on were my bra and silicone breasts, wig and makeup. I had picked out a nice mauve coloured tight fitting silk lace mini slip dress that I thought looked pretty sexy, it came down to just above my knees and hung off my shoulders exposing some of my chest and all of my arms, I had gone out and bought it that morning when I arrived in the city.

My wig which is a shoulder length dirty blonde and my makeup took a little work to make me look pretty I put on false eyelashes and delicate small clip on earrings. After about 30 minutes Jeff knocked on the door and asked if everything was ok, I replied, "Yes I just need a few more minutes pour us another glass of wine and I will be right out."

I finished fixing myself up put on a pair of low healed pump shoes and took a look at myself in the mirror and was satisfied with my looks, before I had left home I had shaved my entire body all except for a little patch of closely trimmed hair above my genitals so my whole body was smooth and felt so sexy with all the silk clothing I had on. I had also been using a cream on my
entire body for a few months so it is smooth and soft. I wanted to look and feel really sexy for Jeff so I took a little more time to get ready then I thought it would.

I opened the door a crack and told Jeff to close his eyes, I slowly walked out into the living room and stood in front of him as sexy as I could. I had done a
lot of reading and studying on line to teach myself how women walked, stood and acted. I told him to open his eyes, I was totally petrified point as this was the first time ever that anyone would see me dressed like a woman in real life. My tummy was doing flip flops a hundred miles an hour.

Jeff opened his eyes and just stared at me for what seemed like hours but was really just a few seconds then said "oh my, oh my your stunning."

I leaned over and took his face in my hands and put my lips on his and we kissed for the first time, we just kissed with our lips for a minute or two and he slowly stared working his tongue in my mouth. I put my hand on his chest a started undoing his shirt buttons one by one. After I had three or four undone I slipped my hand onto his bare chest and massaged his hairy chest
running my fingers through his hair and kissing his neck. We just cuddled and kissed each other for a long time stopping to have a sip of wine once in awhile and totally enjoying each others lips and bodies. He was gently massaging my back and legs through my sexy clothing.

After a long time of kissing and licking his nipples and chest, I took him by the hand pulled him up and led him into the bedroom. I slowly started taking his shirt off undid his belt and pants pulled his pants and underwear down very slowly. When his manhood came into view I couldn't believe how beautiful it was. It was wonderful undressing him and to be able to kiss and
touch his body. Jeff is a very sexy man, not fat just nice and big, a little bit of a belly, and all hairy.

I was in total awe when I finally saw his member, it was as hard as a rock about 8 inches long with a magnificent head when I touched it was so soft and silky-smooth, I slowly took it in my mouth just kissing and licking his head and slowly working my way down this beautiful shaft I took his big balls in my hand and kissed them all over sucking them one at a time gently into my mouth, then pushed him down onto the bed all the while slowly kissed my way down his legs and back up his body until I was laying on him kissing him
on the mouth again.

I could not believe my luck in finding a man that loved the way I dressed for him and took pleasure in me and my body a me kissing him all over his handsome body.

When I was laying on him he was massaging my body now under my clothes and slowly kissing me on the neck and shoulders. After a few minutes of this I said "let me undress for you" he nodded and lay back with his hands
behind his head and watched.

I stood up and slowly pulled my mini slip over my head, as close to a strip tease as I could, revelling my garter nylons panties and bra filled breasts. He lay watching me with his big beautiful manhood standing straight up just inviting me to take care of it. I slowly rolled my panties down my smooth legs, kicked them off and swung my leg over him. I stopped and took a jar of KY jelly from the night stand and rubbed it all over his manhood and some on my bum hole then I sat on his big thing and slowly guided it into my bum ever
so slowly as he was huge.

I gently pushing him into me until I had him completely buried in me, I never felt so full in all my life. I must have made love to him this way for 15, 20 or more minutes I'm really not sure as the feeling was so wonderful I lost all track of time. Jeff caressed and touched me all over at least to places he could reach, and then held me by the hips moving me back and forth up and down until he came deep inside me. He then pulled me down on top of him and held me tight kissing me until his spasms stopped.

After a bit he gently rolled me over and kissed and licked his way all over my smooth silky body until he took my member in his mouth kissing and sucking on it until I was ready to cum, then he stopped and turned me over on my stomach and did the same to the back of my body down to my feet and back up to my bottom where he used his tongue to lick and make love to me with it.

When he rolled me over again and took my member back in his mouth and sucked me to an orgasm that made me almost faint with ecstasy, keeping me in his mouth until I had emptied all of my cum in his mouth. I pulled him up to me so we could snuggle and cuddle and bask in the after glow of the best love making I had ever experienced.

We lay in each others arms until I asked him if he need another glass of wine and a snack. He said he would love both. I got up put on a black baby doll thigh length mesh nightie with an open front and low cut back that I had also bought that morning, gave him a smile and went out to the kitchen to make us a snack and get some more wine. I had always wanted to be a complete woman and doing this made me feel so sexy and feminine and it made me horny as hell, to be looking after my man in the bedroom.

I put every thing on a tray and went back to Jeff who was sitting up in bed with the sheet covering him to his waist and a smile on his face. I sat on the edge of the bed and handed him a glass of wine then took a cracker with cheese and put it in his mouth. We sat and talked as I feed him cheese and crackers, strawberries grapes while caressing his hairy chest. This was so
erotic to me that I was getting to know what a woman would feel like.

After we had ate our fill and drank more wine I noticed a little tent starting to grow under the sheet, so I said "now its time for your desert" and pulled the sheet down and gave him a blowjob sucking him until he filled my mouth with his sweet cum I drank all of his thick juice then licked him clean. I said "now sweet man would you like to have a bath with me" He said " yes that would be great, but I better phone home and tell my wife that I won't be home tonight if that's ok with you." "Oh yes" I whispered "please do, there is
nothing I want more then you to spend the night with me if you can."

I got up and went to the bathroom to start the bath as he picked up his cell phone to make his call.

He came in the bathroom a few minutes later and said "there was no one there but that he left a message that he had been tied up at a meeting and that he was going to get a room in town and would call in the morning."

He helped me get out of my nightie, and gently helped me take off my undergarments, and then we got into the nice hot bath. We soaked for the longest time in the bubbles, cuddling each other and soaping each other just talking about things and sex and what was going to happen after tomorrow morning when we had to go our separate ways, we didn't want to talk about this to much as we were in our own little world at the moment.

We dried each other off, I put my falsies and bra back on as he watched, then put my nightie back on but nothing else as my legs were shaved then waxed the day before so I was a smooth and velvety as any woman. We
went and got back into bed and kissed a snuggled until Jeff put a couple of pillows under my bum to elevate my bottom then he took the KY jelly and while on his knees rubbed ,(so I could watch) it on his gorgeous man thing
then put some on his finger and slid it in my bum, he gently crawled on top of me and kissed me deeply while I guided him into me, he made love to me real slow and gentle all the while kissing me and caressing my breasts and belly, stroking my legs and inner thighs. Making love to me this way allowed us to kiss each other and for me to put my arms and legs around him and
experience what a woman would feel. We made love what seemed like hours this way Jeff just going in and out of me ever so slow and gentle until I could feel him building up with desire then he started pumping me faster and faster and more deliberate thrusts until he exploded in me, which set me off on the most shattering orgasm I ever experienced. We were both exhausted and
he lay on top of me while I hugged and held him and he kissed me long and deep. I didn't want him to get off of me it felt so wonderful and I have never felt so contented.

After we lay in each others arms having a sip of wine I suggested we order a pizza or something as we would be staying in for the rest of the night. He said "good idea: so I phoned a local pizza place and ordered one. They said it would be about 45 minutes so. We snuggled and played lovers until the door bell rang, I hopped up straitened my hair put on a bathrobe that was in the
closet and answered the door as a woman.

The pizza delivery guy was a young guy about 25 or so handed me the pizza and said "that will be $32.50 ma'am." I went and got the money from my wallet and gave him a nice tip for calling me ma'am. I was quite surprised that he didn't look at me funny or anything. I put the pizza on the counter in the kitchen and went in to see if Jeff wanted to eat in bed again or eat out
in the living room.

He suggested that I hop back in bed and we eat later if it was ok with me, I hopped right in and snuggled up nice and close. We cuddled and snuggled for a while then he snuggled up behind me and we drifted off to sleep. I woke up a couple of times to hear him softly snoring and backed up closer, in his sleep he would hold me tighter. His body heat was very nice and felt sooooo good I didn't want it to ever come to an end.

I slept some more then had to go to the bathroom so I carefully slid out form his embrace to go to the bathroom, he quit snoring and was breathing heavy when I left.

After going to the bathroom and fixing myself up I went out to the kitchen for a piece of pizza as I was starving from all our physical love making, and looked at the clock it was 8:30 in the morning we had made love and slept for 18 hours I could hardly believe it had been that long.

I went back in the bedroom and quietly crawled back in Jeff's arms and snuggled my bum in to his manhood area and reached down and took his semi hard man thing and pulled it between my legs, he moaned a bit but didn't wake up for a few minutes until I had him hard and was trying to get it back in my bum he was about half awake when I finally got it started and he took over from there slowly pushing it in and out until he had it all the way in.

He had his hands wrapped around me trusting in and out of me until he came in me again with a powerful load of cum. I rolled over and faced him gave him a big juicy kiss and said, "Good morning." He smiled and said "now that's the way to wake up a man beautiful." I kissed him again and caressed his manhood and balls and asked if he would like to join me for a shower.

We showered for a long time just standing under the hot water kissing and cleaning each other, after I made some coffee and we had some pizza for breakfast which I served him as any good woman would. I was dressed in my
silk night clothes for this and he could not keep his hands off of me he kept touching and caressing me as I sat beside him eating.

We went back to bed for the rest of the morning and made love until it was time for Jeff to go, as he left we promised to see each other again real soon and we had a long lingering kiss as he was leaving, him in his suit and tie and me dressed in my beautiful black baby doll.

I had a nap after Jeff left and then showered and got dressed in my own clothes and went out shopping, I spent the rest of the day window shopping at women's clothing stores just looking at all the nice stuff they had to offer and thinking about what I would ware the next time I got together with Jeff.

Jeff and I e-mailed everyday after that. We made plans to get together again, we would talk about making love to what we would do when we meet.

davesmistress
05-03-2008, 01:04 PM
Thanks for adding this