The Price

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"You'll get everything you want by the time we're done, but we're doing this my way."

I nodded solemnly and she took my hand and led me into her bedroom. She unzipped and removed my sexy dress but would not let me remove any of my other girl clothes. I did kick off my heels which was a great relief. Sherrie pulled off her top and her skirt and then we lay down on the bed together. She kissed me and ran her hands all over me and I ran my hands all over her.

"Since you're my girl, you're going to please me the way a girl would."

She took off her bra and had me kiss and nibble on her breasts. I started kissing her right one, while using my right hand to stroke her left boob. I'd only ever gotten to touch her boobs over her clothes before and I reveled in being able to touch them directly. She was perhaps a b-cup but her boobs were firm and soft.

I switched back and forth between her boobs, kissing, licking, and sucking, while caressing the other one. I had waited for so long just for a chance to touch them directly. I wanted to enjoy it to the utmost and not cut it short in any way. Her nipples were so hard and I sucked on them as though I could get nourishment out of them.

Sherrie seemed to enjoy what I was doing to her titties and neither of us was in any hurry to cut that short. I nibbled slightly at her nipples which made her moan and shove her chest forward. I was in heaven as I made love to her boobs. She grabbed my head and held it tight and stroked it as I continued to work over her love mounds.

She humped my body as I kissed and caressed her boobs. I could hardly wait for us to be doing an even more intimate humping. Before long, she wrapped her legs around my torso and I felt her cum underneath me. She held my body tight for a couple of minutes, before releasing her legs and slumping back on the bed.

"Please, Tommi, go down on me again."

How do you turn that kind of request down? I couldn't. I slid down her body to get closer to her pussy, and she lifted her hips off the bed for me to pull off her panties. Her panties were drenched in her juices, and the musky aroma made me want her even more. Not only were her panties soaked, so was her pussy and all around it.

I began by licking the juices from all around her cunt, never quite touching her vagina. She moaned and squirmed as I licked her. Once I had licked that clean, I licked right up one side of her pussy. She moaned and sighed and moved her hips as I licked both sides of her cute little snatch before doing one big lick right down the center, slightly spreading her lips as I did.

I repeated my licks getting deeper into her twat with every lick, until I had my tongue as far into her as it would go. Her pussy was puffy and red and her scent was almost overpowering. I could see her clit starting to peek out the top of her cunt and started to lick and suck that furiously. As I did that, I eased a finger in her as far as it would go.

I moved my finger slowly in and out of her as I made love to her love button. She wrapped her legs around my shoulders and pulled me tight to her. It was hard as she did that to keep finger fucking her and sucking on her clit, but somehow I did my best. I wanted her to be pleased with me and let me do what gave me pleasure as well.

She was so wet that I nearly felt like I was drowning in her juices, but I figured that might be the best way I could ever go. She reached down and grabbed my hair, almost pulling it out as she shrieked and came for a second time. I licked her pussy and clit frantically until her legs went slack and fell loosely to the sides. I licked her clean as she whimpered and moaned and gently stroked my head.

I moved up the bed to lie beside her and kissed her again, with her juices all over my mouth and face. Sherrie kissed me, almost seeming to devour me before she rolled me only my back and rolled on top of me. After she kissed me for a while, she shifted to one side and unhooked my bra. Honestly, with everything we'd done, I had forgotten how I'd been dressed most of the day.

I still had breast forms glued to my chest, and had no idea how I was supposed to get those off. Sherrie began to play with my breast forms as though they were real boobs. I felt weird, but it seemed to make her happy. Then she slipped down and began to kiss and suck on my faux boobs. Obviously, I had no nerve endings in them but there was still a certain sexual thrill from that.

She seemed to really enjoy my fake titties, and I wanted her to be happy. After a time, she lifted up on my hips, so I raised them from the bed and she pulled off my panties finally freeing my cock which was rock hard and ready for action. After all the time I spent licking her pussy, I hoped she might suck my cock for a while. Instead she rolled on top of me, kissing me again. I could feel my cock sawing away in the space between her legs.

"Well, you've been such a good girl for me today, that it's time for you to get your reward."

With that, she raised her hips, grabbed my cock and rubbed the tip of it up and down her sweet little slit. I almost came, just from that feeling, then she slowly slid my dick deep in her pussy. I could feel her hips up against mine and knew that I had finally reached heaven. She paused, just keeping me deep in her, which probably kept me from going off immediately.

"Well, baby, do you like being in there?"

"That's wonderful, Sherrie."

"There's a lot more wonderful to cum."

She moved her hips back, getting my prick nearly out of her before plunging it in deeply again. She began slow and steady, fucking me, while kissing me constantly. I did my damnedest to think of almost anything else, so I didn't cum in her immediately. I was fairly successful, holding on for several minutes before I grabbed her hips and pulled her tight to fill her cunt with my cum.

The humiliations of the day, and the humiliations of spending the day looking like a girl and being hit on by guys was all forgotten as my balls emptied themselves in her cute little twat. I had my payoff -- the payoff I'd most wanted and what I'd had to do to get there was ancient history. As I came off my high, we resumed kissing.

She began to move and I was worried that we were done, but she shifted about. Now her pussy was by my face, while her face was by my dick. She rolled me on my back then got on me with her pussy over my mouth. She took the head of my cock in her mouth, which made me moan. After a few passes on my prick, she stopped.

"We're going to 69, so you need to lick my pussy as I suck your dick."

With her pussy and ass right over my face, I could smell the tang of her ass as I started to lick her cunt. I was kind of repelled by the smell of her ass, but I liked her pussy, and loved having her suck my cock. I caressed her ass as I stuck my tongue deep in her snatch. I could feel her taking my dick in her mouth, though she didn't seem to be able to deep throat.

I was happy with what she was doing and did my best to try to please her as well. She pressed her pussy firmly into my face and I licked and kissed it as though my life depended on it. As I did that, she was fucking my cock with her mouth. Before too long, I erupted, filling her mouth with my cum. It was hard to focus on her pussy as I came, but I soon resumed licking her and she came shortly after.

Of course I could taste my own cum leaking out of her as I licked her. There wasn't much way to avoid that, but I figured I could handle that. When Sherrie came, she not only humped my face, but she squirted. It kind of shocked me to get a face full of her juice, but it wasn't like I hadn't been lapping it up the whole time.

I cleaned her up as best I could, and could feel her cleaning my cock as I did. Once she settled down, she moved around and we began kissing again. We shared my cum, her cum, and the taste of her lips. I was in heaven and felt our love making was everything I could ever have hoped for. The thoughts of what I'd done earlier in the day were long gone from my mind.

Finally, she spoke. "That was wonderful. Not many women have ever made me squirt."

"What about guys?"

"No guys ever have."

"Except me."

She kissed me before replying. "You're my girl with a dick."

"But I'm a guy."

"Only between your legs. Except for that, you're a girl."

I felt really uneasy and the past day came to the forefront of my thoughts. She was still kissing me, but I'm not sure I was really responding. I became very aware of the breast forms still glued to my chest. I knew, without looking that I was still in makeup, with nails polished and all my body hair shaved off. I squirmed a bit, before Sherrie stopped at looked solemnly at me, still lying on top of me.

"Didn't you enjoy what we just did?"

"It was wonderful. You were wonderful."

"Wouldn't you like to do that again?"

"Sure."

"Maybe even a lot more?"

"I'd love that."

"Every good thing in life has a price."

"What do you mean? What kind of price?"

"We'll talk more about it in the morning. Let's get some sleep."

With that, Sherrie rolled off me. She rolled me onto my side, facing away from her and spooned me from behind, holding one of my faux boobs. I realized just how tired I was, both physically and emotionally, and went to sleep very quickly, with Sherrie holding me.

...........................................................................................................

I woke up the next morning with Sherrie still holding me. It felt quite good, even though I had this lingering suspicion that I should be holding her rather than the reverse. As I remembered how we spent most of the day yesterday, and how I looked, I felt queasy, so I tried to think more about making love to her last night.

Sherrie woke up and began to stroke my fake boobs, then turned me on my back and climbed on top of me. We began to kiss and I stroked one of her boobs with one hand as I caressed her ass with the other hand. She squirmed against me and I could feel my cock getting hard and exploring the gap between her thighs. It felt like fucking Sherrie had been the highlight of my life.

As we started to get really into it, Sherrie got off me, which was a big disappointment. Then she got on her hands and knees on the bed, and while I looked at her, she wiggled her ass at me. I wasn't quite sure what she had in mind, but rolled to my side and reached out for her. She kissed me and let me touch her a bit before wiggling her ass again.

"C'mon girl. Get behind me. Do me doggie style."

I had no idea of what I was doing, but got behind her and moved up close to her ass. She reached behind her, grabbed my prick and guided it into her sweet pussy. I was surprised at how different it felt fucking her this way. It was the same pussy, but the angle made her feel tighter. Look, fucking her feels good any way I do it, but I was damned glad she wanted it this way.

I grabbed her hips and began to slowly pump her. There was no need to rush. I wanted this to last as long as it possibly could. She had her head down on the bed and was moaning as we fucked. She began to move her hips back as I thrust forward, trying to get more of my cock even deeper into her. I was good with that. To me there was no better feeling than having my dick deep in her cunt.

She moaned and then twitched and shrieked as she came on my prick. I could feel her pussy get even tighter on my tool, and it already had been deliciously tight. Sherrie was going to pieces under me as I kept plowing her pussy. I could feel it building as I approached my own orgasm, but tried to hold off and make it last. Finally I couldn't wait any longer and pulled her hips tight and filled her with my cum.

I swear, it was almost like some sort of seizure and after spasms of pleasure I think I passed out. I came to very quickly, slumped over her back. All I could manage was to roll off her and lie on my side on the bed beside her. She turned on her side, facing me and started to kiss me frantically. I could also feel her playing with my fake boobs, which I had almost forgotten about.

We kissed for quite a while, before she stopped and told me we were going to do something else different. I just lay there on the bed as she got up and went to the other side of the room. She came back and I still had my eyes closed as she turned me onto my hands and knees. I thought nothing of it, and was barely even capable of thinking at that point.

She got behind me and before I knew what was happening, I felt something going into my ass. I was almost groggy as I looked around as best I could to see that Sherrie was wearing a strap-on and was starting to fuck my ass with it. There was some pain at first, which quickly turned to pleasure. It made no sense to me that I'd enjoy having her fuck my ass, but I seemed to.

She continued to fuck my ass while I lay there moaning and whimpering. I didn't even realize that her fucking my ass gave me a hard-on until I came on the bed as she fucked me. She kept it up far longer than my dick would ever stay hard, and reduced me to a quivering mess. She finally paused with her strap-on still buried deep in my ass.

"So what did you think of that, girlfriend?"

"You shouldn't have done that."

"And why not?"

"I don't think I liked it."

"You hated it so much that it made you cum?"

"It's like -- gay."

"I'm a woman, and it's a toy. If I were a man with a real cock up your ass, it might be gay. But I'm not, so it's not."

She still had hold of my hips and had that dildo deep in my ass. The truly horrible thing was that it felt good. I didn't like it, because I didn't want to get pleasure from someone fucking my ass, even if it was a woman with a strap-on. She began to move it back and forth a little and I moaned, and sadly, I was moaning from pleasure. She fucked me just a little more before pulling it out of me.

"I'll be nice to you, baby."

"What do you mean?"

"I won't expect you to clean it off."

I looked at her with some combination of pain and horror. "You wouldn't..."

"Unless you really want to, of course."

I shook my head. She laughed and lay beside me on the bed. I rolled my ass away from her and the strap-on that she was still wearing. My ass was still buzzing from the attention, even as my cock was at half staff. She moved forward and kissed me. I kissed her back, but tried to stay as far away from her fake cock as I could.

We kissed for quite a while, before she got out of bed and held out her hand to me. I got out of bed and she led me into the bathroom. She still wore the strap-on, which made me feel a little uneasy, but she took it off in the bathroom and used some sanitary wipes to clean it off. Then we got in the shower together.

She let me soap her up, rubbing her all over her body, then helping her rinse it all off. She did likewise for me. I'm sure we could have showered more quickly if we hadn't spent so much time kissing and fondling each other. My breast forms were still glued on my chest, and she seemed to enjoy playing with them, though I'd much rather be rid of them.

We dried each other off and she brushed out my hair before drying and styling her own. Then she dried and styled my hair, and I could tell she was styling it feminine again. She led me back into her bedroom, then handed me a pair of panties, and a bra. I was hesitant. I had done that most of the day yesterday, but I wasn't sure I wanted to do it again.

"You want me to dress up as a girl again?"

"My parents won't be back until sometime tomorrow."

"Really?"

"Would you like to spend the night with me again tonight, doing all the things we did last night?"

"You bet."

"Then you need to be my girl today."

"How long is this going to go on?"

"At least for now, I'll let you fuck me as long as you dress up for me."

"Why? I don't understand."

"I like girls, but I like cock. The strap-on feels good in my pussy, but your dick feels better."

"You don't need to have me dress like that to get my cock."

"I get the fun of being with a cute girl, but still get a real prick in my pussy."

"So you're going to make me dress up."

"Besides, my parents won't let me have a boy spend the night, but they won't mind if a girl does."

"Are you saying...?"

"We dress you up and you might be able to spend the night even after they come back."

"What if they figure out I'm not really a girl?"

"We just have to make sure they don't."

"How do I come here looking like a girl?"

"If you really want me, you'll figure it out. It's part of the price you pay for having me."

She spent time teaching me how to style my hair and how to do makeup. She dressed me up and we spent the day together as two women, then spent the night making love in her bed. By the time her parents arrived home the next day, I looked like a girl, and her parents okayed me spending the night with her that night.

At least for now, I'm Tommi the girl when I go to see Sherrie. I can't see this as a permanent thing but for now it gets me Sherrie, so I guess I can't complain.


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AnonymousAnonymousover 1 year ago

Sherrie and Tommi seem to have a good thing going! It also seems Sherri has a way to feminize Tommi who truly loves it! Alas where was Sherrie when I was their age? I'm envious!

AnonymousAnonymousover 2 years ago

Hmmm, Very scary Sherrie.

AnonymousAnonymousover 2 years ago

My first pegging experience was not nearly as entertaining as Tommi and Sherrie - after years of begging my wife to let me take her anally she relented on the condition she would get to do the same to me. I liked fucking her flat wide ass because I’m small and the fit was tighter than her pussy. The revelation came once she fucked me - we both loved it. She’s the same height as me but heavier and she really liked the dominance fucking me in the ass gave her. The strap on had a small “hook” that rubbed her clit just right so she came multiple times. And most of all she liked how my small penis shrank even more under her assault. Me? Perhaps I’m just not as masculine as I’d previously thought!

AnonymousAnonymousover 3 years ago
Yeah, maybe

The previous comments got me to thinking, about us guys doing a ton of irrational sh..tuff just to please our womenfolk. At that age, I could definitely relate to his "male requirements" influencing his decisions. Yeah glue on breasts might be pushing the concept, but hey, what guy hasn't put up with their mate, styling their hair, plucking their eyebrow, or drowning your dry elbow in girly smelling goop? Or the ultimate horror: Spitting in a lace handkerchief (in public) to remove a bit of leftover lunch on one's cheek. O.M.G!! Ok, there's some seriously ugly looking cross dressers out there. Also ones who appear to be cross dressers but aren't, so I figure if Tommie has the looks to pull it off, and a girlfriend to bankroll his wardrobe, more power to him. If nothing else he gets a first class education how 50% of the population lives and thinks. As for the story, I think jackie_em spun a pretty good yarn.

LisaBrooksLisaBrooksalmost 4 years ago
Enjoyable

I must say she was pricey! Tommi paid the price and found out it was enjoyable to a point always with apprehension! It was a good thing that Tommi passed as a girl otherwise all would see he was a boy in drag!

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