Sean and I were good friends. When I told him about my cross dressing he completely supported me. He didn’t offer any judgements or assume anything bad about me. Our friendship lasted through high school where he helped me keep my secret from my family. It even lasted into college where we were roommates and he would let me dress in the safety of our room. About the only point of contention that arose from my cross dressing was Sean’s insistence about my gender preference. I tried to explain to him that I could have a desire to dress and be feminine and still be a heterosexual male. Sean just flat out couldn’t believe that. Eventually I met him half way… I agreed with him when he said I was bisexual with a stronger preference toward women. It was either let Sean think I had a latent attraction to men or end our friendship. I chose friendship.
Every Halloween I found a way to dress up as a woman. At first it was an opportunity to go out and not be ‘outed’. It let me try different looks and see how effective they were. By the time we were graduating college I actually went out as a woman in costume. Wonder woman, super girl, maid. You see at that point I could pass in public as a girl so there was no more reason to ‘dress up’ for Halloween. It was even safe to go drinking when I was enfemme. It must have been destiny that my parents gave me a gender natural name like Taylor so that Sean never had to remember a different name depending on how I was dressed.
When Sean got married I was his best man. Only he and I knew that I was wearing stockings, panties, and a garter belt under my tux. I felt a little bad though as I wanted to be completely open with Sean’s wife Caitlyn… but while Sean loved her dearly, he said she just wouldn’t understand my desire to dress. So, it remained hidden. When Sean and Caitlyn had their little girl, I became a Godparent to precious Peyton. I promised both Sean and Caitlyn that I would do anything I could to make sure she was raised from a prefect little girl to a graceful elegant lady. I never thought I’d have to do much as Sean and Caitlyn were perfect parents… right up until Caitlyn passed away.
I helped Sean through his grief and of course that meant taking care of little Peyton a lot. I had a hard time convincing Sean to go out again. He said he didn’t want to ruin the memories of his wife and I tried to insist that he needed to move on with his life. That finding a woman wouldn’t take anything away from the memory of his wife. I eventually convinced him to go out by accompanying him all dressed up. I told him that no woman would try and make a pass at him if they thought he was with me. We had a great time and I got him to open up. I never realized one of his worries was finding a perfect role model for Peyton. At 5 years old she wouldn’t have many memories of her mother, so any woman he went out with would need to be that motherly role to his daughter. When we eventually got back to Sean’s place he was completely drunk and barely able to move. I politely paid the baby sitter and got Sean onto the couch. When I turned around I saw little Peyton looking up at me with a big smile.
The question seemed innocent enough when it was in her pure voice. “Are you Daddy’s girlfriend?” I put my hand up to cover my smile as I blushed and got ready to tell her that I was just a friend when Sean’s drunken voice answered. “That’s right sweety? This is Taylor and she’s my very special girlfriend!” At the time I didn’t think anything of it, and put Peyton back to bed. I got back and helped Sean into his bedroom where he told me to take the bed. He’d sleep on the floor that way Peyton would get used to him having a woman over. As this was a step in the right direction I agreed and stayed the night.
In the morning I dressed up in some of Caitlyn’s clothes to keep the illusion of “Daddy’s Girlfriend” and made Sean and Payton breakfast. I was shocked when Sean turned to Peyton and asked if it was all right that I would be spending a lot of time here. Peyton seemed really excited about the idea as I moved on to cleaning up the kitchen. I spent the entire day as Sean’s girlfriend for Peyton. When I eventually got her down for a nap I found Sean and asked him what he was thinking. He explained that he was really embarrassed by his answer last night and didn’t want to disappoint his daughter. And that this would be perfect in so many ways. Peyton would get a motherly figure, he would get a woman in the house, and I would get to be dressed all the time. When I tried to refuse Sean broke down and cried, saying he didn’t know how he would ever find a woman he could trust his daughter with and insisted saying that as Petyon’s God Mother it was my responsibility to help him raise her. He promised he’d find a woman eventually and that we could ‘break up’ then.
Reluctantly I agreed. Over the next few months both Sean and Peyton got used to me being a woman. I have to admit that I felt a swell of pride when Peyton called me ‘mom’ for the first time, but was a little worried when Sean insisted that she continue to call me that. For Sean’s part there were times that I think he honestly forgot that I wasn’t his girlfriend. At first I thought his actions were just a way to show Peyton how she should expect to be treated, but after a while I noticed that he was acting that way all the time… even when Peyton was away visiting her grandparents. Some of it was innocent enough…. He’d pull out my chair, he’d stand whenever I stood up, he’d open doors for me, e never let me carry stuff around. Some of it was a little old fashioned but fine… he expected me to cook and clean for him, he expected me to do all the shopping, he had me dress to the nines most of the time and even had me wear 50s style house dresses and stockings to ‘relax’ in. And then there was the disturbing things…. He’d stand behind me and give me a shoulder rub while talking about his day, he’d give me kisses on the cheeks and lips, he had us sit together on the couch cuddling with one another, and he’d even give my ass a swat when he was encouraging me to move faster.
And then there was the bedroom. At first I told him we could switch places each night and eventually get a fold away bed instead of sleeping on the floor. But neither of us were happy about that arrangement. One night after a few drinks he simply climbed into bed with me. I was wearing my night dress and he was in his pajamas but it was still very odd to have him spooning me all night. The next night he said that we had both slept better that way and as he held up the blanket for me, insisted that we keep doing it. That lasted for several weeks until one night I climbed into bed like normal. He cuddled up behind me and threw his arm around me like normal. I hid my shiver as I felt his erection grow against my rear. It wasn’t as though I hadn’t’ felt it before and knew that it was just nature as Sean was deep asleep. When I noticed it felt a little different I turned under his arm enough to noticed he wasn’t wearing his pajamas… he was naked.
I brought It up in the morning after getting Peyton off to school, but Sean just shrugged it off. He said that he slept better that way and encouraged me to do the same. I refused, but he kept up telling me I should sleep that way for comforts sake and eventually I met him half way… I slept wearing only my panties. A few nights later I thought I’d have to go back to my previous sleepwear when Peyton came in crying from a nightmare. I had to pull the covers up over my flat chest and Sean had to comfort his daughter on his own. Sean was understanding but angry that he had to risk his daughter seeing him naked, so I relented when he insisted I get some more permanent breast forms.
Like a lot of cross dressers I started using a mix of padded bras and adhesive based breast forms. Unlike those cross dressers I wore my padded bras during the day and my breast forms all night. Eventually, as I feared, I got some really bad skin irritation with the adhesive going on and coming off every day. Sean took me to a doctor friend of his and he said that I’d have to avoid the adhesives for at least three weeks. Neither Sean nor I was pleased to hear this. I had actually gotten used to sleeping in just my panties and didn’t look forward to going back to those confining night dresses.
It was Sean that suggested the breast implants. He brought it up while we were snuggled together on the couch watching a movie, just after I’d put Peyton down to sleep. For every logical reason I brought up to not get breasts implanted in me, he had a logical way to shoot it down. I didn’t want a permanent change…. But it was reversible with minimal scaring. It would stop me from dating… I haven’t dated for months and wouldn’t be dating until I moved out. It would make me more feminine than I wanted to be… It would let me be more feminine around Peyton. I agreed even though I didn’t voice my final concern…. That Sean was already looking at me as more woman than man and this would make it harder for him to remember that I was his friend and not his girl.
The recovery was uneventful and let me have a good conversation with Peyton about how she’ll eventually have breasts of her own. I reluctantly agreed with her hope that hers would be big enough so that she didn’t need the augmentation that I had just got.
Over the next year, life settled into a very normal routine. I eventually gave up my job as an independent programmer. It was great and I never had to meet people in person… but it took to much time from Peyton. Besides, Sean made enough for us to live comfortably. I offered to manage the household income, but Sean just chuckled and said that it was a man’s responsibility. I don’t think he knows how much that hurt. Sean was happy again, Peyton loved having her ‘mom’ around, and I even fell into the role of perfect housewife. Anytime I’d try to talk about Sean meeting new women, he’d just brush it off saying that he’d do it, or that he didn’t have the time to do it right now.
When New Year’s Eve rolled around I hosted a party for Sean’s office. I received a lot of compliments about ‘our’ home and chatted with the other wives for most of the night. It surprised me just how well I could keep up with the conversations no matter where they turned. Talking about makeup, diets, buying kids clothes, selecting schools, cooking, cleaning…. It all came honest and easy. I really was just ‘one of the wives’. I had quite a few drinks as did everybody. When the last couple finally left after 3 AM, I checked in on Peyton and then went into the bedroom. The lights were out so I didn’t notice Sean standing at the foot of the bed. I let out a surprised yelp when he reached out and pulled me into his arms. That yelp was silenced quickly by Sean’s lips. We had kissed many many times, but this was the first time I felt Sean’s passion behind the kiss. I could taste the scotch in his mouth as I’m sure he could taste the wine in mine.
I didn’t struggle or fight against this forced passionate exchange. Maybe it was the drinks, maybe it was the feminine feeling of being with the girls all night, maybe it was the familiarity of being close to Sean, maybe it was even our deep feelings of friendship getting mixed up… but I didn’t struggle even as his hands started to wander over my body. Having cupped many woman’s breasts didn’t prepare me for how good it would feel when Sean’s hands came up and caressed mine. I let out a delighted squeal when his thumbs rubbed over my nipples and he just smiled and shushed me before diving in for another desirous kiss. I felt his hands unzipping my dress and it sliding from my body. When he broke the kiss I finally tried to protest but my words melted into a long sensuous moan as his lips encircled one of my now bare nipples and he started sucking on it.
When he moved to the next nipple he turned me around and sat me on the bed, kneeling between my splayed legs to keep his mouth on my tit. I could feel my erection trying to push past the gaffe and panties I was still wearing but when he pushed me to sit down I sat right on it, causing a gasp of shocked pain to come out. I’m sure Sean thought it was just another gasp of pleasure as he just kept lapping, licking, and sucking at my rock-hard nipples. When he stopped and stood up I bowed my head trying to separate the intense pleasure radiating from my breasts and the dull ache flowing from my crotch.
When I turned my head up I intended to look up into Sean’s eyes but my gaze never made it that far. Instead they stuck on Sean’s hard throbbing cock lined up right with my mouth. My mouth hanging open in surprise must have looked like an invitation because I felt Sean’s hand on the back of my head as he thrust forward, burying half of his manhood into my mouth. He held still for a moment, his hand preventing my attempts to pull back, before starting a slow relentless thrusting in and out. Each time he’d pull out I was hoping he’d pull out completely, letting me close my mouth and tell him to stop. But he never did. I could taste his precum being massaged into my tongue as each thrust went a little deeper. When he brushed up against the entrance of my throat I couldn’t help but gag. He pulled out some, but started back up his relentless thrusting as soon as I was under control. I heard his voice floating above me, slurred with drink and murmured with passion “Mmm… that’s so damned sexy to hear you gag like that Taylor. I won’t last that long this first time but we’ll work past your gag reflex and get you to deep throating next time!”
His voice broke through any fog left in my head. ‘First’ time? ‘Next’ time!!? I in no way wanted to give Sean a blow job once let alone multiple times, but he was to strong for me to pull off of. I raised my hands and raked my nails down his shirt. I heard him gasp, but he never pulled out of my mouth. Instead his free hand grabbed my wrists and seemingly easily held my hands above my head. Being held like that, my wrists clenched in his fist above my head, his hand on the back of my head, his cock slowly and repeatedly sliding in between my lips, but I doubt he lasted more than three minutes. I must have gagged on him four or five times though before he finally burst and filled my mouth with his hot sticky seed. His growl of “Swallow it baby!” was followed by my compliance.
When he finally pulled out of my mouth I was shivering with embarrassment and shame. I didn’t know what to say as emotions raged through my mind. Humiliation, anger, guilt, fury, mortification, rage, self-disgust. As Sean removed the rest of his clothes and climbed into bed I simply followed his motions and laid next to him. I was still silent as I sobbed and he held me close, my face pressed up against his chest. His hand caressed my bare back and I heard him say soothingly “There there… you’ll get better at it dear. I promise. I’ll give you every opportunity to practice as much as you want!”
It would be easy to say that all I felt were those angry and self-reproaching feelings. But I’ve never been one to hide behind the easy… and somewhere deep down I felt good. I had visually and physically pleased ‘my man’. And even if I didn’t do a good job, he was sweet and loving enough to be patient with me and even help me. And below even those harrowing thoughts, there was a part of me that was still aroused. My own unrelieved hard-on was still stiff under my panties.
I fell into a fitful sleep, but was awakened only a half our later according to the bedside clock. Sean had me rolled onto my back and was kneeling over me. His knees were firmly holding my arms down and his hard erect cock was being pointed right at my lips. His face looking down at me held no malice or cruelty or evil… instead all I saw in Sean’s eyes was a deep fervent love. When he softly asked me to open my lips, I did so and let him teach me how to deepthroat. It took hours, but when he came that second time it was delivered straight down my throat on it’s way to my belly.
The New Year will certainly be a changing point. I’m either going to be leaving Sean and Petyon behind and trying to figure out what exactly I’m feeling right now…. Or I’m going to dive far deeper into this role than I ever imagined. And to be honest I have no idea which is going to happen.
source: John Radford Photography