My name is Ashley. I just turned 30. This is my story of my life from age 28.
I first met Steven in a gay bathhouse. I was exploring my bisexual side and had recently lost my anal virginity (painfully!) and given my first few blowjobs. I had started with giving simple hand jobs to other guys and eventually progressed in man to man experience. I soon found out that I was definitely a "bottom". Steven was in a public area within the maze with a full erection. I handled it and said to him how lovely it was but it was too big for my tight little pussy. He said, confidently, that there was only one way to find out! He and I went to a secluded area a short distance away and kissed. Delicious. I never had enjoyed kissing a man before... until him. Then, gently, with some lube, he slid his condom-covered penis into me, filling me completely but without any pain or tearing. He held me in his muscular but slender arms. We eventually had to break off while shooing away some horny onlookers. We went to a private room a bit further away. Inside we kissed again while he guided me down and sucked my uncut member. I cradled his bald stubbled head in my hands as I enjoyed his attentions. After having come earlier in the evening, and him not knowing to pull the foreskin back, I wasn't going to cum anytime so I got him to stop. We exchanged positions so I was now sucking on his thick manly cut cock. I must have been quite good because a few minutes later I was swallowing down his thick creamy load without spilling a drop of his precious baby-making fluid. Then after much tender cuddling, he entered me again from behind but for much longer. I was in heaven. It felt so snug... so right!
Afterwards, we showered together, dried each other and talked some more. He lived in a different city and was only visiting my hometown. He was single with a steady job. Upstairs, we reluctantly kissed and said goodbye after exchanging numbers and email addresses. We actually did keep in weekly email contact. No matter what I was doing, I often thought about him and the few hours we shared. We had made an intimate connection but the distance between our cities prevented any repeats or continuations.
Fast forward a couple of months. I had just lost my job. A few people had to go, and since my performance wasn't as strong as some others, I was let go too. I was devastated. It was getting harder to find decent work, I had to still pay rent, bills and eat! At least I didn't have a car to pay for as well. Public transport was good in my area of town. I thought long and hard for a few days and made my decision. I called him and told him I was planning on visiting his city in a week and could I stay a night or two? He immediately said yes, please. I booked a cheap flight for the week ahead and he said he'd meet me at the airport. With my last week, I packed all of my belongings carefully into boxes, and put them and my furniture into a long term storage facility. The rest was crammed into my suitcase and back pack. I cleaned my place top to toe and gave the real estate agent notice and my parent's address. I hated the idea of having to live with them again if my plan failed. I paid all my bills and was left with under $1000 that I had left from my severance. I took the train to the airport and crossed my fingers...
Within two hours I had touched down and landed in Steven's city. I had never been there before so I was looking forward to seeing the sights... but it was Steven who I wanted so desperately to see. He was at the airport gate. Being discreet he greeted me like a long lost brother with a jovial back slap. We could wait to greet each other properly! We found his car and drove to his small apartment. It was smallish but with a bit of rearrangement of his stuff, it could become more spacious. As soon as the door was closed we literally flew into each other's arms and French kissed for what seemed like ages. We ripped each other's clothes off and ran naked towards his queen bed. "I want you so bad" he cried. "And you're going to have me" I said, but I want to try something with you. I laid down on my back and grabbed a pillow and shoved it under my butt so it raised my hips enough, and spread my legs. He climbed between them and knew what I wanted. I wanted to be made love to missionary style, like a husband does with his wife the first time. He scooted between my thighs, lined himself up and sank slowly into my bowels as I purred contentedly. We were bareback, skin to skin, facing each other, kissing and making love. It was so much more than just sex. It lasted for over an hour as he gently slid in and out of my back passage, and holding himself deep when his penis erupted it's hot salty load of cum into my man-gina. He rolled off as we held each other. Within just one minute I had rubbed my 5 inch man-clit and had come too, but a dribble compared with his big gusher. I fell asleep too, nuzzling into his strong male body. That evening, we repeated the deed, in different positions, another two times. Thank God next day was Sunday or he would have been late for work.
On Sunday he took me out to brunch at a smart local cafe and showed me his local area. We checked out an old bookshop and an antiques shop. We held hands discreetly and even stole a quick mouth kiss. Romance was the mood that morning. We strolled back to his place and made love again in my favourite position -- as the female, missionary style. He really enjoyed this way as the intimacy was so much more. He told me he loved me and I repeated it back as we frenched while he continued his love assault inside me. Later, after I had cleaned up, I asked him if he really meant it and he said he did. I told him about my situation, and he quickly asked -- no, begged -- that I stay with him, and we'd try living together and see how it went. I was so happy I cried like a girl from happiness.
Each day he'd leave for work and come home to a clean house and a cooked meal. He'd share his day while I listened. Then we'd watch TV together, and then make love. Sometimes, we'd try other positions as well, and I'd often give him oral sex and swallow before making him hard again to have the anal penetration we loved to have. To save on washing the sheets often, as I felt his juice slowly leak out of me through the night, I bought a pair of female panty liners that ladies use for the same purpose... and their monthly period. So after making love, I'd discreetly pull on my pair of ladies panties and enjoy not having to sleep in a wet spot in the bed. He loved the idea that his "girlfriend" wore panties and from that day forward he always gently sucked on my nipples during love play.
As the weeks went by, and because my money was now dried up, he gave me a weekly personal and housekeeping allowance and paid my small storage fees and mobile phone bill, too. I was a "kept woman!" I met his close friends and family, and they all approved some because they could see how happy he was. I made some friends with our neighbours who knew we were a couple but never judged us. Often I'd have coffee each day with our other single lesbian neighbour Stacy. We were like two girls together with our conversation. We traded confidences, and I told her I wear panties at night. She said, detecting something that I was not even aware myself, that why don't you try wearing them all the time. So I bought a few new pairs and did just that. I became hooked. They were more comfy than the boxers!
Stacy also encouraged me to get my facial hair electrolysed so I wouldn't grow whiskers again. She encouraged me to get a full Brazilian, eyebrow shaping, grow my hair long with an androgynous style that really suited me. She was turning me into a woman, and Steve loved it too as the changes were slow but steady. I started becoming Ashleigh from Ashley. Stacy's next step in my feminization was for me to start taking birth control pills that she got for me. She said to try a month and see how you feel. So I tried and actually enjoyed the hormone surges. My body became more sensitive and more shapely. I'd lost excess weight I had carried by my daily walks and although I became fitter, I didn't get unsightly man muscles. My hips widened a little. My voice became softer. And I came nearly every time my darling Steve sucked my budding breasts! Because the changes were so gradual over many months, Steve and I didn't become unattractive to each other, nor did he freak out. Despite being gay, we could walk closely and I'd be mistaken for his girlfriend. I was his girl, but I was anatomically male.
Within six months, my hair was long, I unconsciously swayed my hips when walking, and had B cup breasts which required a bra. Steve loved undressing me wearing panties and bra. Stacy even bought me a dress, skirt and blouse and the three of us went out. I was mistaken for a girl when wearing makeup. Steve loved to tell me in bed how much he loved my oversize clit and pussy. I often moaned and begged my lover to fuck me harder and sperm my cunt... which he did. On our one year anniversary, he got down on bended knee and proposed. I accepted. I looked into states and cities that permit gay marriage. I even stealthily looked for hospitals that do gender reassignment. I was now almost woman, except for my dick and balls. Steve loved to take me out publicly because I looked like a woman. It was marvellous to hold hands without needing to be discreet. And when I went out with Steve and Stacy, Stacy loved popping into the girl's loo with me nervously in tow. Steve loved the way I'd changed. He was fed regularly, had a hot girlfriend, was fucked silly anytime he wanted it, and lived in an immaculately kept flat with all the typical female touches that our hetero neighbours had in theirs. Life was good...