A Valentines Day Surprise

By MICHAEL MATARAZZO

Published on Jan 21, 2025

Transgender

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Chapter 1

Hi my name is Louis I am 36 yrs old and at this point of my life I am very single. I drive a limo and spend most of my time working and not dating I guess you could say when it comes to work im a type A personality. My boss loves it because I am almost always available to do another job. Well after one particularly long day I decided to turn off my phone and go for a drink. Little did I know that this drink would change my whole life.

The bar I was in was very crowded it was one week before Thanksgiving and everyone was starting to make their way home from school and work to visit family for the holiday. There were 2 seats at the bar so I took one and ordered a rusty nail. With in minutes a woman came I and sat next to me she was beyond beautiful and I was a bit intimidated to speak to her but she spoke to me first hi my name is Lisa she said. And as unbelievable as it may seem we hit it off from the start. The night just flew by I am pretty sure with the way we were feeling from all the drinks that I could have slept with her that night but I didn't want to ruin it the first night. You see Moet women find me very attractive I am 6ft tall 180lbs olive complexion and I do try to keep myself in good shape. But I am not much in the penis size department when hard I may top out at 5inches, this has ruined more then one relationship and I was liking this one. She was at least 5,9 nice large breasts thin waist and an ass that was so perfect and on top of it all she had a great personality! So we exchanged numbers and she was gone.

The next morning to my surprise my phone rings and it was her she said she thought of me all night and had to call me first thing this morning. She is very successful and has a highpaying job in the market so she does have more time then I do we made checked our schedules and made dinner plans for the following week.

Finally we meet again after many days talking on the phone and dinner was great we just had so much in common now we started to see each other regularly but I avoided sex with her because I just loved her company and did not want to lose her over the fact that I was so small. I always thought that my extra effort was enough for play and such but most of the women I was with got tired of the for play and a few pumps from a small penis.

Now weeks turned into a month and it was Christmas Eve and Lisa made an intimate dinner for us at her beautiful apartment I knew going in that tonight would be the sex night and even though I was scared I was very horny for her and hoped that she knew me well enough.;

The night went well a great dinner nice bottles of wine and fire in her fireplace alll so romantic and I was ready we kissed and felt each other for the longest time I slowly removed her top and pants she took off me shirt as well her tits were more beautiful in person the I ever imagined as I removed her bra she moaned so loudly as I began to suck her big nipples she was on fire, her pussy was so wet that her panties were soaked before I even touched them and when I did she had on of the most powerful orgasums I ever saw I woman have I carried her to her bedroom laid her on the bed and licked her pussy until she was screaming to me to plaease fuck her she begged PLEASE PLEASE FUCK ME NOW I NEED TO BE FILLED WITH YOUR DICK. At this point I still did not let her touch me so when I finally pulled down my pant she didn't see me penis my fingers worked over time on her clit and she was begging to be fucked so now the moment of truth I stuck my dick into her all the way to the base and I could see the look one her face but she was good and went with it. I know my fingers mad her feel better then my dick but w ent on anyway and she made me feel like a champion when I came so did she both of us screaming I thought it was found my woman. When I slid off her she moved into my arms and whispered in my ear that she loved me I was in heaven. We both slept well when I woke up she was gone already She left me a note saying what I wonderful time she had and she couldn't wait to do it again boy was I happy.

So Christmas came and went so did New Years but we never had sex again. We were a couple but there was no sex. She introduced me to a couple of the guys she worked with and we started to go to the gym together Paul was 6,2 and really good looking John was a bit shorter but he was GQ all the way the first time I saw these guys at the gym we had a great workout they rally razed me because they thought Lisa was so beautiful and she never even tried to date them. At the end of our workout we hit the showers and these guys came in Paul had the biggest dick I had ever seen he was at least 7inches long soft and John was not far behind them boy was I jealous

Finally one night Lisa came home and told me she had a big surprise for me she made reservation for us to go to turks for Valentines Day the week before we were scheduled to leave she said she wanted me to sleep over for the week that she had a special surprise for me and I had to be there to get it. Well I packed my bags and moved In for the week I was disappointed though because she had her period that week and we could not have sex but we did everything else the first night she explained other me that she loved men with big nipples and would I be ok with her putting this new cream she bought that was supposed to increase the size of my nipples boy I didn't care and agreed to right off so the first night she stripped me naked and she removed everything except her panties and prceeded to rub my nipple with the sweet smelling cream it was so exciting I was hard in sceconds and jus said she would take care of it and sucked my dick like a pro she was great at it she could eep throat my dick so easy and swallow every drop if my cum. When we woke up she applied the cream to my apples again and told me to leave it on all day. Well while I worked that day my nipple started to itch and get warm it was very erotic. That night when I arrived home Lisa answered the door in only her panties dragged me in and applied the nipple cream again this stuff was ammazing after only one day it seemed to make my areoles bigger but the best part was the slow blow job I got after. This went o for 3 days. And each day my nipples looked bigger she was now able to bite and chew them and it made me so horny.

On the forth day once again she answered the door in only her panties but today she had a drink in her had a pink drink in a martini glass with a little umbrella. She told me that this was the drink of the resort we were going to so she wanted me to drink one every night when I came home which was ok with me. Valentines day this year was on a Friday and we were scheduled to leave for vacation on Wednesday morning just 2 days away. Well after the drink and the nipple cream when I woke up on day number 5 I noticed some new changes the hair on my arms and legs were gone my beard was almost on existent and my penis even felt a little smaller then it had been but this area was doing the job only nipples I ow had huge areoles and long pointed nipples that were so sensitive the air gave e a harden. I was now getting nipple cream three times a day and the great pink drinks I was enjoying two time a day as well Lisa was so excited with my nipples and progress she could seem to stop sucking them and my dick. Looking in the mirror it started to look like my whole body was changing not just my nipples I seem to have a rounder ass my waist was thinner and almost every hair on my body was gone. The hair on my head was growing must faster as well and I was so horny almost all the time.

The Tuesday came Lisa rubbed my nipples so well that I came and she never touched my now very small dick. There area around my nipples was growing as well this morning it looked like I had small breasts more then an A cup. Looking in the mirror I looked more like a girl then a man now my hair was longer my waist was even smaller and my breasts looked so feline.

The difference was I didn't care any more about the size of my penis because she seemed so happy with me she kept telling me she loved me I was blind to what was happening. After a wild time of sucking her nipples and her sucking mine she decided to let me know that this was a clothing optional resort we were going to so I didn't have to bring a lot of cloths. I told her with the size of my nipples and the way it was looking like I was growing small breasts that I was a very self conscience of going out in public my dick was almost gone at this point and I didn't want to be embarrassed.

She went to her room and came back with a very tiny bikini and told me to try it out, if I was so imbarrassed by my body at least I could cover it up little. I told her no im a man that I couldn't wear a bikini she told me look in the mirror do you look that much like a man any way she said we were going to be on an island where nobody knew us so what the difference and she gave me another pink drink. So just for fun I tried on the bikini it was white and barely covered my nipples and my small breasts the bottoms cover my dick nicely but my pubic hair stuck out the sides and made it look funny. Lisa couldn't stop laughing my tiny dick in the bikini and the hair looked like a man with a beard. But she was prepared she took me by the hand to the bathroom and proceeded to give me my first Brazilian wax that was something i will never forget my balls were now the size of raisins and my penie hard was maybe 2inches long. Looking in the mirror at me in the bikini with my tiny breasts my now much longer hair i really did look like a young girl. It really made me horny to look at myself my dick started to leak some kind of fluid when I touched ut and smelled it it smelled like pussy it began to leak a lot and the tast was also pussy this was crazy what was happening to me. Lisa took my bikini bottom off and tasted my dick and love the flavor she told me it was fine.

The next morning when I woke up I found Lisa sucking my nipples my breasts not seem to have grown in the night and I came 2 time from her just touching my now b sized breasts. She said she loved my breasts and told me secretly that even though she has never been with a woman that was always one of her fantisys. We spent so much time suck nipples that we almost missed the plane there flight was great Lisa rubber the cream on my nipples 2 time under the blanket while we flew and I came both times. She also managed to bring a pink drink with her which she feed to me instead of breakfast bot I love vacation.

When we arrived at the resort everything seems very normal the lobby was big and everyone was dressed. Lisa arranged for us to have a poolside room and rented us a cabana near the pool. The we got to our room I changed into my bikinni and Lisa just stripped naked. It made me jealous to think everyone would see her naked but she explains that everyone was like that and nobody would really be looking at her. My bikini looked great the top stretched around my now larger b cup breasts and I looked very hot and we made our way out to the pool. The day was beautiful everyone was naked normally I would be drowning over some of this women topless but for some reason today al I could think about was all the men and the sizes of thiner dicks. The closer o got the the more my tiny penis would leak juices by lunch time I was so hot I could barely sit still. I notice Lisa was also leaking plenty of fluid so we ran back to our room and licked and played with each other until our orgasems became a blur. my tiny little dick was now 2 inches long hard and when I tried to mount Lisa I ttook all my effort to put it in her rubbuing it in and out I came what would be my last cum as a man.

Such much cum seeped from my tiny dick and over flowed her wet pussy she went wild and I fell asleep inside of her for the very last time.

When we woke the next morning Lisa was standing over me asking how I was feeling. I felt pretty good she told me not to lose my mind but after me last cum my body complete the change. She said that I was now a full female. I reached down and what was a small dick the hight before was no a clitorus and a opening for my vagina, I felt my breasts where now fully grown and were perfect d cups my hair was shoulders length and the most beautiful auburn. She kissed me deeply and hugged me. Al I kept asking her was why would she do this to me she said after the first night she knew that my tiny dick would never ne able toe satisfy her and she loved me so much that she want to find a way to keep me in her life forever. So she found the pink drug and cream which would change me into a woman.

She the came to me and started to lick my now huge breasts feeding me hers and licking my whole body. I orgasmed as a woman for the first time and it was intense we 69 nd until she made me squirt .

When we were finished she showered together and we dressed for dinner yes dinners were dressed lol. Tomorrow I the day before Valentines day and Lisa has explained that she still had a very big surprise for me. Lisa brought a very sexy dress for me the clevage was cut so low and the bottom of th skirt barely coveraerd my pussy. Even though this change has happened slowly and I love my new look I am not so sure being a woman was what I wanted fro the beginnig. Lisa came out fully dressed as well and looked so hot her dress was skin tight and showed of every curve she had she entered the room and came right to me and kissed like I have never been kissed before.he tongue searched my mouth and her hand went to my breasts it made me so hot if she continued dinner would have been a second thought. We held hands as we walked into the restaurant and even though this was a nude resort every eye in the place landed on Lisa and I .

After dinner Lisa kept laughing and asking if I was happy and yes sex was so much better as a woman I am not embarrassed of my dick anymore but I kind miss it She told me that she wasn't sure she would be happy with a woman but with me she has never been this happy. We made our way back to the room my first day as a woman was coming to an end as we entered Lisa moved me right to the couch and slowly removed my dress and licked my ears then my breasts my nipples hardened immediately and my pussy became so wet the juices were flowing down my legs Lisa slowly worked her was down my body taking her time at each spot that would make me tingle her finger moved over my clit and she held it like a small penis she sucked it slowly into her mouth my whole body began the shiver and shake she slowly inserted her finger into me and I came with such force I almost passed out. I don't even remember her taking off her dress but as pleasured me her body moved around so he pussy was over my pace her juices were flowing she tasted like honey and woman and I couldn't get enough we ate each other until I just passed out from the pleasure.

The next morning the sun woke me by shinning in my eyes the sound of the ocean and people in the pool woke me up and I felt so good as I ran my hands over my large breasts and caressed my virgina this is as close to heaven as you can get. I took a long hot shower while Lisa ordered us some breakfast we ate in the nude near the terrace enjoying the sights of all the naked people every penis that passed our terrace was bigger then mine was what a surprise.

After breakfast Lisa ask me almost joking is I was the bikini girl again today or weather I was going to take my new body out for a naked stroll. She didn't know while I was I the shower I tried to put the bikini on the bottoms were fine but the top no longer fit over my breasts so this bikini was out of the question. I smiled at her and told her I was nude for the rest of the vacation.

Ok so we are going for a day of first for this new girl today will be my very first time naked in public either as a man of a woman but I must say I am more confident walking out there as a woman then I ever would have been as man at leaset today I won't have to try and hide my penis. I must admit that I starting to stare at the penis and comparing them to on another I am start to wonder what it would be like to feel one maybe taste one I think I may have a hymen since nothing other the Lisas fingers have been in there.

Ive been busy sunning when Lisa came out to finally sit with me she explained that my surprise was yet to come she said it may be time to check to see if I was a real girl or just a girl wanna be.

All of a sudden to me surprise Paul entered our tent and not far behind him was John both naked both smiling Paul looked me right in the eyes and smiled and said I look so much better today then I did when we first meet and boy today his dick looked so much better then it did in the gym. The four of us sat and drank in the sun Paul took me for a swim all was very normal except I cannot keep my mind off his dick I want so bad to reach out a touch is my pussy is leaking like the thought of his dick is effecting me more then I ever thought it would.i need to speak with Lisa I cannot do this with out her I am in love with her and I am not about to spoil our relationship. We got back to the tent and Lisa seems to ave the same idea with John as I did with Paul only she was a more experienced girl then I was when we walked in Lisa had johns hard dick in her mouth im not sure if I was jealous or envious she really knew her way around a dick. Paul got instantly hard when he saw this action and his dick was huge ive never seen anything that big it made my so wet I wanted to jump in and take advantage of this situation but Lisa stopped me in my tracks. I don't know why she already sucked off John behind my back but she was insistent.

This was my surprise Paul knew I liked his dick and he wanted to be the first to make love to me. There was nothing I want more then to try sucking Pauls dick and maybe if it was right try to fit it into my pussy. But there was an issue Lisa explained that my new body and new me was temporary and would wear off in a month the change back would be painful but I could be a man agin after the month transition. There is one way to make it permanent all I had to was swallow I load of sperm. I was pretty sure Lisa wanted the change to be permanent but as amazing it may seem I am still on the fence about it.

I went back to my room to use the bath room and when I came out Paul was waiting for me his dick was still hard and my hornyness was fogging my brain as I got closer to him he touched my arm with sent shivers throughout my body his huge dick l wasn't helping standing straight-out slowly I moved towards him the desire throughout my entire body was clouding my judgment. I ws horny Paul took my taste the feel hand and moved it to his large dick the heat from is skin and the firmness of his dick made me even more arrosed then I already was I was loving this new body my nipples were so got so hard my pussy was so wet I need more Paul guided me to my knees and his dick was now eye level he began to rub my tits and nipples with each stroke my need became more intense the head if Pauls dick is waving in my face and the need just took over I licked the head and slowly sucked the head into my mouth I was in heaven the taste the feel increased my arrosal I wanted to stick the whole thing in my mouth as I moved my head down up down till it hit the back of my throat but only about 3-4 inches made it all the way in my mouth. My whole body was tingling Paul squeezed my tits and rubber my nipples till with even my pussy touched I was on the verge of the most wild orgasum I ever had. I took a deep breath and slid my mouth down his cock and my throat opened and his entire length slid down my throat. I had to be carful because if he came in my mouth I would be a woman forever do I ant that or do I want to go back. Suddenly he pulled out of my mouth and picked me up and tossed me onto the bed his body was perfect his dick so beautiful he climbed on top of me and pushed towards the entrance of my virgina I wanted him to have me virginity I pushed towards him as he pushed into me my Hyman bust and I came so violently I almost passed out he slide in slowly but I wanted more I love this feeling I ever had anything like this as a man I ws actually a great lover as a woman 100 time better then I ever was as a man did I want t=his forever did I want to stay a woman the answer was easy Paul began to grunt I felt his cock get bigger inside of me I knew what I had to do just as he was ready to cum I rolled him onto his back pulled his dick out of me and moved my mouth onto him just she started to cum it seems like a gallon of his semen shot from his dickinto my mouth and down my throat I swallowed ever drop and tried for more as he finished cuming there was a bright light in my head and I collapsed onto the bed my design was made this body was mine forever there was no NO going back I ws happy and feel asleep.

When I woke the next morning Paul was gone and Lisa was lying

next to me it was Valentines day she was holding a red rose

and a pick umbrella drink she looked me in my eyes and asked

me if she was going to be a lesbian or a straight woman for

the rest of her life I leaned in kissed her deeply and told I

was her woman forever.

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