My name is Jaime, and this is my story. I was always slight of build, with delicate features. I seemed to top out at about 5’4” and 130 pounds with a face that looked like it could be either a boy or a girl. When puberty hit, I didn’t get the body hair that most of the other boys got. I desperately hoped for a beard, but could never get more than a few stray hairs or patches of hair, generally pretty unsightly. Though long hair was kind of stylish, I kept mine short. Too many people thought I was a girl as it was.
I tried being one of the guys, but all the other boys seemed interested in was cars, sports, hunting, fishing, guns, and making rude comments about girls. When I wasn’t as macho as some of the other boys, some of them started calling me a faggot, and asking me to suck their dicks. I decided I really didn’t need that kind of shit, and I was interested in girls, not boys.
I ended up hanging out more with the girls, though none of them had any interest in me. At least they were friendly and most of them were not abusive like the boys were. A few times, I had girls start calling me names, but the others girls told them to shut the fuck up. I became the ‘safe boy’ the one they could talk to when their boyfriends hurt them. They could cry on my shoulder, hug me, and kiss me on the cheek. I was safe, because I knew my place. I was not going to make out with them, and I certainly had no chance of fucking them.
After high school, I started community college. My family didn’t have much money and I couldn’t afford any more than that, besides I was a pretty average student – no real genius. I hung in long enough to get a two year degree, then my money and interest ran out. At least that degree was enough to help me get an office type job. Given my lack of muscle, I sure didn’t want to do physical labor.
I found myself doing customer service work – hardly thrilling, but it was honest work in a nice air conditioned office. Most of my co-workers were women, and a bunch of the men there were gay. I ended up hanging with the women, much like I did in school. As long as I wasn’t loud, obnoxious, or pushy, which I never was, they were happy for me to hang with them.
I figured my fate was to always be the guy who women see as a friend, but never as a lover. Then something happened to change that. Looking back at everything that happened, I wonder if I had it to do over again, knowing what would happen as a result, what I would do. I honestly don’t know. I wanted love and to be wanted and needed, but the price was more than I’d have been comfortable with.
Susan joined the company and became part of the group of women I hung with. Susan was about 24, compared to my 21, with a pretty face, and she carried herself with a sense of self confidence. She was about my height, but with nice curves, shoulder length brown hair, a smile that could melt hearts, along with c-cup breasts.
At first, she seemed much like the others, then slowly things began to change. When she hugged me, the hugs seemed to be longer and somehow more intimate. She seemed to be physically closer to me than any of the other women were. I never wanted to get my hopes up only to be disappointed, so I kind of dismissed it and laughed it off.
I’d go out drinking with the girls and as it went on, Susan and I were often among the last to leave. In my case, I wanted the company. Hanging with the women was far better than sitting in my tiny studio apartment by myself watching cable TV, which is what I did all too often.
One Friday evening, it was getting to be eleven or so, and the group had melted down to me, Susan and one other woman. Susan seemed to be talking mostly to me, hanging on me, and laughing at everything I said. After a little bit, the other woman stood up, gave a little half laugh, and spoke.
“I can see that three has become a crowd. Goodnight, ladies.”
She turned and walked out of the place, as we watched her.
“Ladies? Obviously she isn’t looking very closely at you, is she?”
“It doesn’t bother me. One night, one of the women said, ‘No offense intended, but you’re just like one of the girls’.”
Susan looked at me, then smiled, and leaned forward and kissed me on the lips. I was surprised, and didn’t even know how to react. Honestly, I’d never kissed a woman romantically, nor had one kiss me that way. She pulled back slightly and looked at me again.
“Was that terrible?’
“No! It was great.”
“You didn’t act like it was great.”
“You surprised me. I didn’t know how to react.”
“You’ve had a minute to think about it. How should you react?”
With that, she lifted her head slightly and opened her lips just a little. I sat for a second, then leaned forward and kissed her. She kissed me back, and we sat kissing, though not as much as I’d have liked, before she broke the kiss.
“You’re sweet, but you need kissing lessons.”
“Where am I going to get kissing lessons. None of the women want to kiss me.”
“Aren’t I a woman?”
“Yes. I didn’t mean…”
“And didn’t I kiss you?”
“Yes. And it was great.”
I felt anxious and looked sheepish, as she looked at me with a little half smile on her face.
“I’d love to have you teach me to kiss.”
“I could do that, and a lot more – provided…”
“Provided you understand that I am in charge.”
“You’ll do what I say, when I say. If I say do it, you will. If I say stop, you’ll stop. No arguments – period.”
“Okay. I’ll do it.”
“Let’s go back to my place. It’s a little more private and we can talk about it and get to know each other better.”
I’d never had a woman invite me to her place. I’d never had one willing to come to my place – for any reason, even an innocent one. Here was this gorgeous woman, inviting me to come to her place, and hinting we could kiss, and maybe even more. At that point I’d have sold my soul for that chance, and in one sense I guess I did.
Her place was close by, a nice little one bedroom apartment with a comfortable sofa in the living room. She invited me to sit down and asked me if I’d like a glass of wine. The group had largely been drinking wine that night, and I’d been drinking it as well, so I accepted. Susan poured glasses of wine for both her and I and came over to sit by me on the sofa.
I took a big drink of the wine, because I was nervous as hell. She took a sip of wine, then set her glass down on the coffee table in front of us, and had me do likewise.
“Different women like different things, but for the most part, we don’t want you to simply glue your lips to ours and try to shove your tongue down our throats. Be sweeter, take it a little slower. Let me demonstrate.”
She leaned forward and pulled me closer to her, then first just brushed her lips against mine, then again a bit firmer. She kept at it, from different angles, with varying firmness, even using her tongue to brush my lips. I’d never been so excited in my life, but tried paying attention and doing to her what she was doing to me. Sometimes we’d lock lips hard and she’d have a quick swipe of her tongue deeper in my mouth. I sat there kissing her, thinking nothing could be better than this. She stopped and leaned back, which disappointed me.
“You’re doing well, and learning quickly. You know, we can do even more, but like I said you have to be willing to do whatever I tell you.”
“I will, you bet I will.”
“I sometimes have kinky tastes. You have to do whatever, even if it’s kinky.”
“Kinky? How kinky?”
“We won’t leave scars or bruises, at least nothing anyone can see. Are we agreed?”
“Yes or no.”
“Then unbutton my top.”
I couldn’t believe she was asking me to unbutton her top, but I was sure not going to question it. I reached out and with shaky fingers began to undo the buttons. It was a light blue and came down to her waist, but did not tuck in her skirt, though it didn’t show any midriff. In spite of my fumbling, I got all the buttons undone. She leaned forward, with her arms back slightly.
“Open it up, and take it off me.”
I opened it wide and slid it down her shoulders and arms and she turned slightly to let me take it all the way off her. She wore a lacy white bra which showed just a hint of her areolas, though not the nipples themselves. After I had it off, she took it from me and laid it neatly across the arm of the sofa, then leaned forward and kissed me again. I kissed her back eagerly and was not sure what was coming, but felt sure I’d remember it. After we kissed for a minute, she pulled away again and turned her back toward me.
“Can you unhook my bra?”
If I was shaky before, just imagine what I was like now. I reached out and pulled the back of the bra slightly away from her back, then fumbled to unhook the two sides, but managed in spite of my clumsiness. I let go of the two ends of the bra.
“Massage my back where the straps were. Firmly but tenderly.”
I rubbed across her back where the main straps had been and could see some red marks from wearing the bra.
“Go up also.”
I followed the shoulder straps up her back rubbing there as well. She moaned and rocked back and forth as I rubbed her and the shoulder straps slipped off her shoulders and the bra dropped off her.
“The shoulders, and up into the neck.”
My hands aren’t that strong, but I began to knead her shoulders and her neck. I kept at it until my hands began to tire. Finally, she turned toward me and I got my first good look at her breasts. Sure I’d seen photos of boobs, but this was the first time I’d seen any in person with my own eyes. I think my mouth hung open from the shock. She kissed me again.
“You’ve earned a reward. Touch them, sweetly and tenderly, but firmly – don’t tickle.”
I could see my hands shaking as I reached for her boobs with both hands. She smiled as I put my hands on them and rubbed my thumbs across the nipples. I gently squeezed them and slowly pulled away tugging at the nipples. Susan moaned and closed her eyes as I slowly worked her boobs over, marveling at how warm and soft they felt and how good it felt to play with them. The nipples were hard and she moaned every time I touched them.
“Kiss them. Kiss the nipples. Suck on them.”
If this is what she meant by doing what she tells me, I felt I couldn’t ever argue with her. I leaned forward, taking the nipple of her right breast in my lips, kissing and sucking on it as I continued to play with her other breast with my right hand. Susan leaned back on the sofa as I kissed and sucked on her boobs, switching back and forth from the right to left and back again repeatedly.
“Take your shirt off and hug me. I want to feel your skin against mine.”
I was so eager to do that, I actually ripped a button loose in my frenzy. I had a tee shirt under my shirt and pulled it off as well. Then I pulled her to me feeling her firm nipples scraping against my chest. I looked in her eyes, and she opened her lips a bit, so I kissed her. As we kissed, I rubbed her back, then snuck a hand around to tease her left boob or what I could get at of it.
We stood. She took me by the hand and led me to her bedroom. She walked me to the bed, then turned to face me.
“Unzip my skirt.”
At this point I was so far into terra incognita that I wasn’t even nervous any more. I reached out undid the button at the top of her skirt, then unzipped it. I let go of the zipper and the skirt fell to the floor at her feet. She stepped out of her skirt and kicked off her shoes, so she was now only in her panties in front of me.
“Take off your pants.”
I kicked off my shoes, not even bothering to untie them, then undid my belt, unzipped my pants, let them fall to my feet and stepped out of them. Susan sat on the bed, leaned back and pulled me down on top of her. We kissed, caressed and played with each other for a long time, shifting positions, sometimes side by side, sometimes me on top, and sometimes her. At one point she rolled off me, and stopped me from rolling onto her. She lifted her hips off the bed.
“Take off my panties. Then take off yours.”
I pulled her panties down, and as I did she dropped her hips back to the bed and lifted her feet so I could pull them all the way off. I flung them across the room, then took off my undershorts. I thought maybe she was ready to have me in her, but instead she pulled my head down to her pussy and spread her legs. She was completely shaved down there and her pussy was open in front of me.
I stuck my tongue out and licked her slit from the bottom to the top. As I reached the top, her clit peeked out from the folds, just a little bit. I took the little nub between my lips and sucked on it, as she gasped and pushed her pussy into my face. Her pussy lips spread open further and her clit stuck out more. I stuck my tongue into her slit and kissed licked and sucked on her pussy and clit like there was no tomorrow. I felt like if I died that night, my life would have been complete.
She moaned and wrapped her legs around my neck, pulling me closer and tighter to her. I got my hands back into the whole thing by grabbing her ass and massaging that as I worked her pussy over. She rocked back and forth, then arched her back, grabbing my head in her hands and holding it so tight to her that I could barely breathe. Her juices flowed freely, until she actually squirted in my mouth and on my face.
After she settled back down again, she let my head go and no longer held my neck tight with her legs. She unwrapped her legs and pulled me up her body to lie on top of her. She kissed me, tasting her own juices on my mouth and face.
“Jaime, if you can do what you’re told, you’re a keeper. I think you deserve your reward.”
She lifted up on my hips and I lifted them off her. She reached down, grabbed my dick and guided it into her pussy. I was a little concerned, because my dick isn’t all that big, and I was worried she’d be disappointed. I was about to say something when she smiled, kissed me, and spoke.
“That feels marvelous. Do it boy. Fuck me.”
I could feel her pussy gripping my dick and it felt like nothing ever before. Okay, I’ve wanked myself, but it never felt anything like this. I eased it out then back in, moaning as I did it.
“Do it. Faster. Harder.”
I pumped away, enjoying it, and feeling that if I never got another chance, it was still more than worth it. I realized I was about to come, and told her. In the meantime, she’d wrapped her legs around my waist and as I started to come, pulled me deep inside her. I collapsed onto her, almost unconscious from the feelings. As I regained my senses, I looked at her, and kissed her.
“God, I love you Susan.”
“And if you can be a good boy and do what you’re told, there’s a lot more to come. Unless you’re just happy fucking me once, then never again.”
“I want to do this with you for a long time to come.”
I woke up the next morning in bed with my head on her shoulder, with my mouth near her breast. For just a second, I wondered if last night and the morning had just been part of some fantastic wet dream. Susan woke up and stroked my head. I looked up at her and we kissed.
For days after that, we went back to her place and made love at night. Since we had to go to work most mornings, she told me I could bring some of my clothes over for when I stayed the night, which now seemed to be every night. After a couple of weeks, I simply moved in and let my studio apartment go. I contributed to the rent at her place. Slowly the changes began.
“Those tighty whities you wear are horrible. First, white undershorts are so last millennium, and second they’ve started to turn gray. We need to get you something new and pretty.”
“Something to make you look sexy.”
“I want you to wear some nice panties.”
“You mean like…?”
“That’s exactly what I mean.”
“I can’t wear panties.”
“What would the other people in the office think?”
“You go around showing your underwear to the other people in the office?”
“Then how would they ever know? If you’re worried, pee in a stall, just don’t drop pants and panties all the way to the floor and no one will ever be able to tell.”
“It doesn’t feel right.”
“You said you’d do what I ask you to. I’m asking you to wear panties. If you aren’t going to do what I ask, then move back out and see if you can find another girlfriend. Remember, I told you I was a little kinky.”
We went out shopping and she bought me several pair of panties, all very feminine. I was concerned about how I’d keep my penis in the panties. It’s small, but there isn’t much room in the crotch. She took me to a specialty store and bought me a gaff to tuck my dick out of the way. The woman there explained in detail how to use it. I was embarrassed, but listened.
I asked the clerk how she knew so much about putting on a gaff and she said she wore one before her operation. I think my eyes about bugged out of my head. She kissed me on the cheek, and I looked carefully at her. I’d never have thought she was once a guy. Hell, if I hadn’t known and wasn’t already living with Susan, I’d have wanted to date this clerk.
At any rate, I began wearing the gaff and the panties to work as well as at home and whenever we went out together. I felt weird as shit at first, but after a while, it just began to feel normal. One evening Susan and I were at home and she was shaving around her pussy, and using hair removal cream on her legs. After she finished, she had me come over and she began putting depilatory crème on my legs.
“What… what are you doing?”
“ I’m cleaning this nasty hair off your legs. You don’t have as much as most guys, but I don’t like hair on you any more than I like it on me.”
“I want you to get rid of your body hair, just like I get rid of mine. Fair is fair.”
“If people know…”
“Who are you taking your clothes off around, besides me?”
“Then who else will know? And competitive male swimmers shave all their body hair. It isn’t just women. Besides, you know our deal.”
She used the cream on my arms and legs and that pathetic amount of chest hair I had. Then she got her razor and shaved my underarms and around my dick and balls. Again, it felt weird at first, then I kind of got used to it. Now my smooth body and her smooth body rubbed together and I felt sensations that had been slightly blocked by the hair.
Meantime our sex life was still going great guns. We fucked nearly every night, except when she had her period, and even then we did plenty short of fucking. Before long she decided she wanted to add another twist to our love making. Susan had or got a strap-on and wanted to fuck me in the ass with it.
“You stick a dick in me all the time. You even stick it in my ass when I’m on my period. Why is my ass open game and yours off limits?”
“Isn’t that gay?”
“Nothing that a man and woman do together in bed is gay. It’s only gay if you do it with another man or I do it with another woman.”
She had me get on my hands and knees on the bed. Susan got behind me with the strap-on.
“Look, I’ll use plenty of lube on it so it’s more comfortable for you.”
In my nervousness, I think my ass tightened up considerably, but she didn’t rush. She lubed a finger and eased it in. Once it was moving easily in my ass, she stuck in a second finger. That was a little tougher, but slowly I relaxed and it moved okay. She pulled her fingers out and began to ease the strap-on into my ass. I thought it would feel horrible, but in fact, it wasn’t that bad.
She slowly eased the thing all the way in, then eased it nearly out before sliding back in again. Before long she had a good rhythm going and I could feel the fake dick fucking my ass. I just tried to relax and let it happen to make Susan happy. I didn’t even notice my dick had gotten hard, until I came with her fucking my ass.
She stopped with the dick in my ass, while I spurted all over the bed. She held onto my hips to keep it in there as I almost collapsed from the orgasm. Finally she let go and let me sink onto the bed as the strap-on eased its way back out of my ass. She rolled me on my side and lay down alongside me.
“Why do I think that someone who was reluctant enjoyed it a lot more than he thought he would?”
We began adding that to our regular fucking routine, and before long, when the strap-on was clean, she even had me sucking on it. I mean, I was still repelled at the thought of sucking or being fucked by a real dick, but I kind of got used to this.
After a few weeks, Susan came home with what appeared to be a pointed mushroom with a glass jewel on the end. It was a butt plug and she had two, one pink and one blue.
“You’re mine and I’m yours. We don’t have rings because we aren’t married, but this is a way for us to show the link we have. I’ll wear one and you wear the other.”
How was I going to argue with her? Was it worth moving out and losing her? And kind of like the panties and shaving, how would anyone beside us ever know. Besides which at this point I was getting used to having her stick things in my ass. I took the blue one and she took the pink. She put mine in my ass, and I put hers in her ass.
Every time Susan asked me to do something weird like this, our fucking would be particularly intense and long lasting. She became a real sex machine in bed for days afterwards.
Susan said she had some pills that would help inhibit my body and facial hair, and she had me start taking them every day. Sure enough, I noticed I was getting less hair, particularly on my face, and the body hair was lighter and finer. After a few weeks, I noticed my nipples getting a lot more sensitive. The areolas seemed to get larger as well. I didn’t understand and mentioned something to her.
When I took off my shirt, she ran her hands over my nipples and I felt almost electric shocks of pleasure. I know that doesn’t make sense, but that’s the only way I can describe it. She stroked my nipples as I just lay back and was astounded by the sensations. She then put her lips on one nipple and began sucking on it. I thought I was going to levitate off the bed. I couldn’t have even imagined that having a woman touch and suck my nipples could feel so good. I didn’t come like spurting, but I felt rolling waves of pleasure going through my body.
Needless to say,, we now had something new to add to our sex play. Later she told me she’d checked and found that was one of the side effects of the pills that inhibited hair. Only months later did I realize she’d lied to me. I was taking hormones that blocked male hormones and supplied female hormones. Before long, I began to grow boobs.
Susan dismissed that, saying lots of men had man-boobs. It was nothing unusual. Well, no it wasn’t unusual for men taking hormones to transition to female. Before long I easily had a-cup boobs, and had to wear tight tee shirts to keep my boobs hidden at work. Every now and then someone would give me a funny look, but no one at work ever said anything.
One Friday night, we went home before going out.
“Jaime, dear. I was you to dress up extra special for me tonight. We aren’t going out with the usual group. It’ll just be you and me some place different.”
“Okay. What do you want me to wear?”
“I’ll find some things and dress you. Take off everything but your panties.”
I undressed, with my little boobs kind of dangling, which embarrassed me. As she walked by, she stopped and kissed each boob in turn. She produced a bra which would not hold her boobs, but was the right size for mine.
“You want me to wear a bra in public?”
“Yes, I do. And you will wear it. Besides by the time I’m done no one will notice.”
I put the bra on, though Susan had to help me fasten it. She then produced a pink pullover top and had me put it on. I was starting to get uneasy. She came up to me, stroked my body and kissed me.
“Trust me. When I’m done, no one will even recognize you as the Jaime I work with. Besides we’re going some place where the other work folks don’t go.”
She put a skirt on me that didn’t quite come to my knees. She then sat me down and painted my fingernails a bright red. She then plucked my eyebrows slightly to shape them, and made up my face. I sat there in shock as she did this. Base, eyeliner, eye shadow, lipstick – if I looked like I was even going to protest, she put her finger to my lips to hush me. Finally she pulled a blonde wig out of her closet and put it on me.
“We’ve let your hair get a little longer, but it isn’t quite long enough for this yet. Give it a couple of months, we’ll get there.”
Obviously she was saying she planned to do this again, probably more than once. I wanted to cry, but was almost numb. I couldn’t find the tears, and besides it would have messed up my makeup and Susan would have been mad at me.
“Jaime is not only my special boy, you’re also my special girl. I do love you so, and you know you’ll get your reward later.”
She put me in a pair of two inch wedge heels.
“You can’t handle serious heels. We’ll get there though.”
I looked in the mirror and I didn’t recognize me. I saw a pretty blonde girl, dressed to kill. Back in the day I’d have killed to get that girl – now I was that girl.
Susan dressed and we went to a club we’d never been to before. It was way on the other side of town and almost hidden. We walked in and I didn’t recognize a single person there, and was very relieved. As I looked about, I noticed that most of the guys were dancing with other guys, and most of the women danced with other women. Susan noticed my looking around, smiled, and stroked my head before kissing me.
“Don’t worry honey. Most of the guys here won’t have any interest in you – at least as long as they think you’re a girl. Just make sure if you go to the bathroom, to use the women’s.”
I hadn’t even thought that far ahead, but realized I sure didn’t want to walk in a men’s room dressed like this. We found a table and got some drinks. We sipped our drinks, and with a little alcohol, I was starting to relax. A very masculine looking woman came over to our table.
“Hey, Suzie-Q. Haven’t seen much of you for a while. Guess I know why now. You found yourself a new little squeeze.”
“Hey, Jill. This is my girlfriend, Jaime.”
“Damn girl. You better keep a tight hold on Jaime, or I’ll steal her away from you.”
“Go ahead and try. I’m not sure you’ll get far.”
“I… Susan and I live together.”
“Got her locked down, huh. Have fun girls.”
She laughed and walked off. I was surprised how many women came over and talked to us. I was even more surprised how many flirted with me. As a guy, no one even paid any attention to me. Now that I appeared to be a woman, half the women in this place seem to want me. I said something to Susan about it.
“You’re fresh meat. They’ve never seen you before or slept with you and you’re cute enough to catch their attention.”
After we’d had a drink or two we got up and danced. We found ourselves in the middle of a bunch of women. Half the time I couldn’t be completely sure who I was dancing with. A slow number came on and Susan slow danced with me. I let her lead. I’m not a good enough dancer to lead.
That number ended and another slow number came on and a gorgeous woman asked if she could cut in and grabbed me around the waist and danced with me. She snuggled close to me and ran her hand all over my ass while we danced. At the end of the number she gave me a passionate kiss and felt up my boobs. I turned to go back to Susan, and another woman grabbed me.
“Hey honey, dance with me.”
“I have to get back to…”
“She can do without you for one more dance. Come on beautiful, dance with me.”
This woman was groping me like nobody’s business. My gaff was holding me very tight, otherwise she’d have felt my prick when her hand went down there. It almost felt like I was being sexually assaulted on the dance floor. The dance ended and she kissed me and groped me some more. I started to try to break free and she held on until Susan appeared.
“Okay, bitch. You’ve had your fun. Jaime’s taken, so go find someone else.”
The woman glared at Susan who stood her ground. Several other women and men gathered around. As they were facing off, a female bouncer grabbed the other woman’s arm.
“Okay Charlotte. Go back and play with your friends. We aren’t going to have any trouble here now, are we?”
Charlotte glared at the bouncer, then at Susan, and stomped off away from us. Susan and I went back to our table and got another drink. A little later, I saw Charlotte leave with another woman. Later on the bouncer came over to our table.
“Sorry about that. She gets really pushy after she’s had too many drinks.”
“That’s okay. It was just that Jaime didn’t know how to handle her.”
The bouncer looked me over very carefully.
“Jaime, huh. She’s trans, isn’t she.”
I didn’t know what the hell she was talking about, but Susan obviously did.
“Just come out. Hasn’t had bottom surgery though.”
“You pass real well, honey.”
“So is she going all the way?”
“Not for the time being. Still trying to decide her direction. You’ll keep that on the downlow though, right?”
“Sure thing, Suze. Don’t want to run off this pretty lady. I’d be half tempted to go for her, even knowing she’s still got a package.”
We left shortly after and went home. We had some of the wildest sex we’d had in weeks. After we were both exhausted from fucking, I asked what the bouncer had meant. Susan told me not to worry about it for now.
The next morning, I was going to clean off all the makeup and change to boy clothes. Susan asked me to stay that way and go to the mall with her. I felt really weird, but did it. She put me in another outfit and open toe flats. She touched up my makeup and we went out.
At the mall, there was a nail salon. Susan dragged me in there for a pedicure. They massaged my feet, cleaned off the callus, trimmed and shaped my toenails, then painted them. We gave it a little time to dry, then walked the mall and went clothes shopping. Susan bought me a few more girl outfits. I had to go in the women’s dressing rooms to try on some of the clothes and once I’d done it a few times, it didn’t even matter.
We had to pee, and Susan walked me into the women’s restroom. I’d been in the women’s room last night at the bar, but it felt different at the mall. I had to pee though, so I did it, washed my hands and left.
As we walked through the mall, a couple of young guys tried hitting up on us – both Susan and me, and seemed every bit as interested in me as in Susan. Susan made some polite excuses and got us away from them. We were walking back to the car, when a guy in the parking lot yelled out to us.
“Hey, baby. I’d sure love to get my hands on that ass. You bet.”
“Take it easy and just ignore him. He’s trying to get a rise out of you.”
We got in our car and drove off, and I’d swear I thought I saw that guy pass us in traffic a little later. We got back home and Susan suggested we go out again that night, with me still dressed as a woman.
“We won’t go back to the same place as last night, but I think we’ll be just fine.”
At that point, I was almost becoming numb to how I was dressed. We showered, Susan redid my makeup and explained what she was doing and how as she did.
“Before long you’ll be able to do your own makeup just fine.”
“Please don’t make me go to work this way. Please.”
“No, I’m not going to do that. This is just for when you and I go out and take a walk on the wild side.”
“I don’t know how much wild I can handle.”
We went to another bar, and while it didn’t have the gay men and women of the other place, no one seemed to care about two women dancing together. We went home after and had more wild sex.
Monday morning, Susan helped me clean off my makeup and took the polish off my fingernails. I wanted her to take off the toenail polish but she refused.
“Jaime, dear, you aren’t going to take off your shoes and socks at work. No one will know you have polish on your toenails. Besides it looks so pretty.”
That kind of set the tone for how life went for a while. Susan dressed me up as a girl for out weekends, and I kept toenail polish on, just as I did my panties, butt plug, and gaff. Generally when we went out, Susan would tell any guys who approached us that we were on a girl’s night and weren’t looking for company. Usually that was enough to drive off most of them. Bouncers took care of the rest. We went back to the gay bar and hung with the lesbians pretty regularly, but not every weekend.
My boobs kept growing until I was a b-cup. I really had to work at it to hide them while at work. I started wearing a binder on my chest while I was there. In some ways I began to feel freer evenings and weekends when I could just wear a bra on them.
Frequently when we were out, guys would ask us to dance. Usually Susan would decline, but once in a while she’d suggest we just dance with the guys for a dance or two, just to make it easier to get rid of them. Fast dances were great, but particularly at first, I was uncomfortable slow dancing with a guy. I did it to make Susan happy, because she did plenty of things to make me happy.
One night we were at a club, and during a slow dance, the guy was groping me and feeling me up all over. He grabbed my ass, my boobs, and even down over my groin. Thank God for my gaff that made my dick disappear. Susan told me how angry guys might get if they found I had a dick. At the end of the dance, he kissed me and continued to grope me until I could break away from him.
I went over to the table where Susan stood with two other guys. I’d had a bit to drink and was still reeling from the assault on the dance floor. As I walked up, one of them turned to me.
“Damn. That was a hell of a show on the dance floor. I almost didn’t recognize you, Jaime.”
I realized the two guys were Dave and Mike from work. I was shocked and scared. No one from work, except Susan, of course, knew I dressed this way at times. And I was doing it for Susan, not because I particularly wanted to, even though I was enjoying it. Hell, as a woman, I was popular. As a guy, I was no one. Now that was all going to be upset.
“Got a good pic of you kissing that guy as he fondled you. The office should love that.”
“He… kissed me, I didn’t kiss him. Please don’t show that around the office.”
“You seemed to be getting into that kiss. And shouldn’t everyone have a chance to see the real you?”
“I do this on weekends. When we go out. I don’t…”
“Yeah. Sure. Even on the fast dance, you were shaking that ass like nobody’s business.”
“Please. I’m begging you, don’t show that picture around the office.”
“What’s it worth to you to have us keep your secret?”
“I don’t really have much money.”
“There’s other things you could do.”
Susan decided to jump into the conversation at this point.
“Boys, this is not the place to discuss this. Let’s go back to our place and we can work this out as friends.”
Dave and Mike had come out in one car, and Susan and I in another. Since Dave and Mike didn’t know where we lived, I rode with Dave, giving him directions, while Mike rode with Susan.
“You ain’t much as a guy, but you’re pretty hot as a girl.”
I didn’t know what to say. I didn’t want to make him mad, but didn’t want to encourage him either. As it turned out, he didn’t need any encouragement, and neither did Mike. What Dave and Mike wanted for their silence was me to suck them off and let them fuck my ass. Now Susan had me suck off her strap on, and regularly fucked my ass with it, but I’d never done either with a man with a real dick.
Susan told me it was blackmail and extortion, but unless I wanted to be outed at the office, I probably needed to go along with it. I didn’t care for it, but realized she was probably right. I didn’t want the whole office to know I dressed as a woman – even if it was only on weekends. She said she’d try to ease into it and see if we could get them to settle for less than they wanted.
“You know, boys, she has real boobs – small ones, but kind of nice. Would you like to see them and touch them?”
Of course they wanted to. Susan pulled my top off and unhooked my bra, to let my boobs out.
“Damn, girl. You been hiding shit from us.”
Dave started playing with one boob as Mike played with the other one. Having these guys touch me kind of disturbed me, but as they played with them and sucked on them, it began to feel pretty damned good. At one point, I had one mouth on each boob, sucking, licking, and kissing them like they’d never seen boobs before. I had waves of pleasure ripping through my body as they enjoyed my boobs.
“That was nice for the prelims, but let’s get down to business.”
Dave stood up, unzipped his pants, and pulled out his prick. I looked at him, and his face was consumed with lust. Mike was nearby and touching his groin. Susan grimaced, but nodded. I edged forward and took the head of his dick in my mouth. Dave moaned.
“God, baby. Do it. Suck that dick.”
I could taste a little of his precum on his dick, as I slowly took the shaft into my mouth until I almost gagged. I closed my eyes and pretended it was Susan with her strap-on. At least I tried to. The feel was different, the taste was different, and Dave moaned as I pistoned his dick in and out of my mouth. To keep from choking on it, I put my hand around the base of his dick and rubbed it as I worked on the rest of it.
Dave’s groans and moans became louder and more frequent until he grabbed my head and pulled it to him. I almost choked as his dick went down my throat, particularly when he came in a great gush right into my throat.
“Swallow it, bitch.”
I didn’t really have much choice. Half of it was down my throat before I could have done anything else. Dave smiled and stroked my head.
“You’re a good little dick sucker, girl.”
Mike was next, and it went pretty much the same. I hoped after sucking them off that they’d be happy and let it go. But both of them insisted on fucking my ass as well. Dave had recovered first and unzipped my skirt and pulled it off. He took my panties off, but my gaff covered my asshole, so he pulled that off too. My tiny dick popped loose.
“Not much there, but it isn’t going to get any use from us anyhow. Cute little plug there, girl.”
Dave tugged at my butt plug and I tried to relax the muscles as he eased it out of my ass.
“Look boys. You have to use lube. I’m not going to let you ruin her or hurt her. And gently, boys, gently.”
Susan produced the lube and Dave smeared it on his dick and around my asshole. I got down on my hands and knees, like I do for Susan, when she fucks my ass. Dave came up behind me and grabbed my hips. I could feel the head of his dick against my asshole as he eased forward. It was already stretched a bit from pulling out the plug, and he slid in pretty easily. Susan had been fucking my ass, but the flesh and blood dick felt different. He pressed in until I could feel his balls slap my ass.
“Damn. Nice to go real deep. Better than I could get with her mouth.”
Dave started slow, building up speed, shoving his dick deep into my ass with each stroke, holding my hips tight to guide it. He went faster and faster and I almost forgot it was a guy fucking my ass, until with a groan, he pulled my hips tight against him with his dick as far in me as he could get it. I felt it throbbing and knew he had just cum in my ass. As he came, so did I, squirting my cum onto the bed as he shot his in my ass.
“Isn’t that cute. The little girl came at the same time.”
Dave pulled out of my ass and came around in front of me.
“Girl, you ought to lick it clean.”
I was appalled, then Susan spoke up.
“I kiss those lips. I’m not kissing shit. You want it clean, go to the bathroom and wash it off.”
Dave looked disappointed and sat down as Mike positioned himself behind me.
“If you’re going to be that way, then I get another pass at that ass.”
“Whatever. She’s not sucking your dick after it’s been in her ass.”
Mike fucked my ass, then Dave fucked me again, then Mike once more. Finally they seemed satisfied. I kind of curled up in a ball naked, sitting up on the bed. Dave and Mike put their clothes back on.
“Good night, girls. We’ll see you again next week.”
“Bitch. You want us to keep quiet, then you can put out.”
They left and Susan locked the door behind them. She came over and sat next to me on the bed and held me in her arms. She rocked me back and forth for a while, until I relaxed, then gently and sweetly made love to me. No more ass action that night. My ass had already had a workout. But she stroked my body, caressed my boobs, then took my little dick up into her pussy and I fucked her, before we curled up together and went to sleep.
I was nervous at work on Monday, but no one seemed to act any different, except Dave and Mike who occasionally leered at me. Dave came by leaned over and whispered quietly in my ear.
“See you Friday night, babe. I’m looking forward to it.”
The next two Friday nights were a replay of the first one, with Dave and Mike getting sucked off then fucking my ass a couple of times. The terrible thing was, I was getting off on it physically, even though I hated it emotionally. After that third week, Susan and I were lying in bed together.
“You know there is one way to get rid of them and end this.”
“How do we do that?”
“The only thing they have against you is photos of you partying, dressed as a woman. We tell HR that you are transitioning to a woman and will be dressing that way at work. You dress as a woman at work, and they don’t have anything over you anymore.”
“Go to work dressed as a woman?”
“What’s worse, fucking the two of them every week, or dressing as a woman at work?”
“I don’t care for either choice, but I’ll go to work as a woman, if it means I don’t have to fuck them again.”
“That’s my girl.”
We talked to HR on Monday, and starting Tuesday, I came to work dressed as a woman. Dave and Mike were puzzled, then angry when Susan told them they could find someone else to fuck over. I’d been going to bars and clubs dressed this way, so it wasn’t much different going to work this way. Most of the women seemed happy for me and I had no problems using the women’s restroom.
Everything seemed to settle back down, and Susan and I seemed happy and loving together at home and going out together. As time passed, I found it became difficult for me to get a hard on, or to keep it long enough to fuck Susan. I was disappointed but we did still have a sex life. Finally Susan decided to address the issue.
“You know, that thing isn’t doing you or me any good as it is.”
“So what do we do?”
“Change it out. Have surgery. Switch from a useless dick to a pussy that we could both use.”
“You want me to get rid of my dick and get a pussy?”
“Why not? You dress as a woman. You live as a woman. You can’t make love like a man anymore. Get a pussy that we can both enjoy.”
“I don’t know if I’m ready for that.”
“We’ve been together for awhile now. Do this and after you’re healed, we’ll get married. And I’d rather be with a woman with a pussy that works, than someone with a dick that doesn’t.”
“After. You got accumulated vacation for the surgery, and I’ve got vacation to be able to take care of you while you’re recovering. And I swear, I’ll never ask you for anything more that you’re uncomfortable with.”
Of course, she had already been checking out doctors. We scheduled it and the two of us went together. Susan held my hand as I went under, and was holding my hand as I woke up. Even with the drugs, it hurt like hell down there. It took two days before they took out the packing. After they did, they told me about dilating my new vagina.
I had to start out dilating it four times a day to keep it stretched out properly, and it hurt like hell doing it. Dilation is essentially taking a dildo, lubing it and sticking it in my vagina. The tissues there had been totally reworked and were recovering from that, which is why everything hurt so much. It felt weird thinking in terms of having a vagina. No, my dick had been largely non-functional, but it was still a dick.
Susan was with me most of the time during recovery, comforting me, kissing me, and caring for me. I hated the dilation, but Susan and the doctor told me it was necessary, so I kept at it. It happened slowly enough that I didn’t notice it but slowly, it quit hurting as I dilated. What shocked me was the day I stuck my dilator in and it felt good for the first time.
I took it slow and easy – I didn’t want to mess anything up. I eased the dilator in and out of my pussy, and instead of the pain I once felt, I now felt pleasure. I began rocking my hips back and forth as I slowly and gently fucked myself with the dilator, until I leaned back, arched my back and had a full on orgasm, like nothing I’d ever felt before.
Susan was out running errands when all that happened, but I told her when she returned. She kissed me very sweetly and told me that while we still needed to take it easy, we could now start to have some fun.
We both returned to work shortly after that. I still had to take it easy and walked for exercise and to stretch all those things out. At work, some of the women hugged and kissed me. Yeah, there were a few who were cold, but that always happens.
We made plans for a small wedding and Susan and I went out shopping for wedding dresses. I wore a lacy white dress, which came down just below the knees, while Susan wore a silky white dress. I remember looking in the mirror at how I looked, which was marvelous, but then thinking back to the nerdy guy I’d once been. I’d gained something, but I shed a tear over what I’d lost on the way.
Looking back, I know that Susan had this all planned from the beginning. She picked a guy who would be so grateful for her love and affection that he wouldn’t balk at the slow steady small changes. By the time the changes became material, I was so far along, it was almost impossible to go back. It is done. I am who I am now, and I am hers and she is mine. The Jaime I was before is dead. Jaime, the girl, is carrying on as best she can.