Jaime's Journey

byjackie_em©

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?"

"Provided you understand that I am in charge."

"Sure. Absolutlely."

"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?"

"Well... I..."

"Yes or no."

"Yes."

"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.

"Stand up."

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."

"Pretty?"

"Something to make you look sexy."

"Like what?"

"I want you to wear some nice panties."

"You mean like...?"

"That's exactly what I mean."

"I can't wear panties."

"Why not?"

"What would the other people in the office think?"

"You go around showing your underwear to the other people in the office?"

"No, but..."

"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."

"But..."

"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?"

"No one."

"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.

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byjackie_em© 11 comments/ 36908 views/ 35 favorites

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