Helping Charley

By Amber Fountaine

Published on Apr 24, 2010

Transgender

Controls

Amber Fountaine stories contain sexually explicit descriptions of consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include gay and bisexual activity as well as any combination of piss play, diapers, cross-dressing and other fetishes and perversions that may please the author's whims. The characters in these stories are fictional, but are mostly based on the author's true experiences, as well as the experiences of others he has met. Every attempt to conceal these identities has been made. These stories are placed in Nifty for the enjoyment of its readers and are not to be copied and/or distributed without the approval of the author.

Helping Charley

by Amber Fountaine

"I haven't had any pussy in three months," Charley complained as he finished his beer.

I smiled and offered him another, not exactly excited or sympathetic hearing him complain about his sex life. Compared to mine, his was still better, yet I couldn't tell him that. I'd been divorced a year and it had been at least a month prior to our separation when I'd last fucked my ex. Since then ol' Rosie Palm had been my best girl. So I tried to change the subject. "Maybe we could get tickets to the game tomorrow. Didn't you say you knew someone that could get us tickets?"

"Yeah, but shit Jim . . . it's forecast to rain beginning tonight and for most of the weekend. I didn't go to a dozen games the whole time I was in college. Why drive over a hundred miles to get there and back so we can sit in the freezing fucking rain to watch a game I could give a shit about?"

I was trying to find some way to cheer up Charley and it seemed like to me that he was even more determined to feel sorry for himself. "Well fuck it," I said, giving up. "I was just trying to find some way to cheer up your mopey ass."

"The only thing that's gonna cheer up my ass is to get some ass. I've seen all the hotties running around here. Surely you know someone that will help a guy out."

I had to laugh. He was right about the fact that there were a slew of women, most of them college age, younger than us, and I was sure if I'd taken the time to get to know any of them, that there were probably several that would gladly give Charley just what he needed. But my ex had done a number on my head before we separated. I'd never been that much of a hand with the ladies to begin with and by the time Gwen got done with me, I'd become convinced attempting to have a relationship with a woman was a waste of my time. But I couldn't tell Charley that I'd never so much as tried to bed any of the available women around the apartment complex. Instead, I sort of wheedled out of it.

"There are a lot of women around here, but they're not as easy as you think. If they were, I'd have one over here right now instead of your grumpy ass."

"Fuck you Jim. I'm not grumpy. I just need my dick drained."

"The bathroom is right in there," I told him pointing at the bathroom door. "If you need to pee, I'd appreciate it if you used the toilet."

"Piss on you. That's not what I meant and you know it. But it's a good idea."

"Pissing on me? No thank you."

"Ass hole. I meant using the bathroom. Besides, you liked it the last time I pissed on you."

I'd screwed up giving him a chance to mention that. He'd made the remark as he'd turned and walked to the bathroom so he didn't see me blush. He had pissed on me years back and I had enjoyed it. We'd been fifteen at the time and had gotten drunk drinking beer in his backyard while his parents were out of town and his sister was staying with a friend. There were several things that had happened that weekend. However neither of us had talked about that weekend in the near fifteen years since it had happened.

But I'd thought about it - a lot. Actually, I suppose it would be more accurate to say I'd fantasized about it - a lot. I'd discovered a few things about myself that weekend that I was still in denial about fifteen years later. I'd even tried some of it with my ex. But since Charley had never mentioned it, and I certainly wasn't going to bring it up, I'd hoped that Charley had been just as eager to forget it all. Yet it seemed that apparently he still remembered it too.

"Some buddy you are," he told me, walking back in the room, still zipping his pants and drawing my attention to the problem he was having with his fly. "I was sure if I came over here for a couple of days you could help me out."

"Yeah, sure. Like Barbara is really going to appreciate me getting you a strange piece of ass just because she's pregnant with your kid."

He gave me a grin that let me know he'd probably had more than just the three beers he'd drank since he got to my apartment. "What makes you so sure she's carrying my child?"

I didn't see Charley and Barbara all that often since I'd gotten divorced but I had no reason to think Barb had been cheating on him. But maybe she had and that's why he felt justified in cheating on her - with my help. For lack of a better response, I asked him, "Well if it's not yours, whose would it be?"

He opened his mouth as if to answer, then stopped, looked me in the eye, and then shrugged. "Lot you don't know," he muttered, looking away.

I was astounded. "You mean that? Barbara was running around on you?"

"Oh shit no dumb ass. Remember that party I tried to get you and Gwen to go to with us? Well we went anyway - and to a bunch more like it."

I remembered all right. Gwen wouldn't let me forget. It had been a couple of years back and Charley had let me know that the party was for swingers or wife swappers or whatever they were called. He'd told me that if Gwen was up for it, he'd get us an invitation and the four of us could go. He and Barb had discussed it and they'd concluded that they'd like for someone they knew to go with them the first time they tried it. Like a dumbass, I'd tried to talk Gwen into it, as she'd been receptive to me trying a few other things, but that had been the proverbial straw that broke the camel's back. From that night forward, she'd started calling me a pervert, telling me I was sick, and those were the nicer things she'd said.

Then, without any prompting on my part, Charley began staring at the only picture on any of my apartment walls, as if he was really intrigued by it, yet he wasn't looking at it at all. I'd have worried if he had. It was a piece of crap picture the furniture rental company had thrown in for free. His mind was on something else entirely.

He started explaining how Barbara had wanted to get pregnant and how after trying unsuccessfully for years he'd gone to the doctor and found out some illness from his childhood, prior to when we'd become friends, had given him a low sperm count. Rather than just pick a donor, they'd decided to let fate take a hand. "But now that she's pregnant, she's decided we shouldn't have sex for the last trimester. And she doesn't want me going to any of those parties without her. She should be having that kid any day now and no telling how long it will be after that."

"Well you were always bragging about what great head she gave you. Doesn't that help?"

"Yeah it would if she still did it. But she cut that out even before we quit fuckin'. I think I miss that more than anything. Even worse, if I jack off, she thinks that's being selfish and that I'm thinking only of my own needs. Shit yes I'm thinking of my own needs. Maybe if women had a hard dick and blue balls they'd know what we go through."

I had to laugh. That sounded so very much like the things that Gwen used to tell me about men not understanding women. Eventually I'd used one of those remarks to my advantage.

Somehow I got Charley off the subject of his sex life long enough to determine he was serious about spending the rest of the weekend. Barbara's mom and sister had both driven in because of Barbara expecting the baby any day. Charley couldn't stand his mother in law and she felt exactly the same about Charley. He described his sister-in-law as being exactly like her mom except four inches shorter and four foot bigger around. "She's never met a donut she didn't like," Charley once told me, "And she's got the old bitches attitude to boot." I'd met them only once when they'd had some sort of party after Charley and Barbara had run off to get married. Barbara's mom was certain that Charley had talked Barbara into doing that just so she couldn't have a big wedding for her daughter - the only one with a chance of getting married.

"I don't expect you to put me up forever," Charley slurred, opening another beer, "Just until the old bitch leaves town."

"No problem. I've got an extra set of sheets and you can sleep on the couch."

"Good idea." Then he went back to teasing me about that weekend in our teens. "Too bad I didn't think to bring one of Barb's nighties and some of her other sexy stuff. I could dress you up like that weekend you wore Adele's things . . . and maybe get you to finish what you started."

I didn't know if he was serious or testing me or what. We'd never spoken about that weekend. Now here we were, for the second time, fifteen years later, bringing it up. "That was a long time ago," I told him. "We were kids then and pretty damn drunk too."

"Yeah we were," he said, grinning and nodding his head. "Have another beer!"

"Shit head. I'm not taking any chances passing out the way you're acting. I could wake up with a sore asshole."

He grinned at me lasciviously. "Yeah. You might. But I'd rather fuck that pretty face of yours. You don't know how many times I've thought about how close you came to doing that and wishing that you had."

He wasn't the only one. In fact I'd have bet I'd thought about it ten times more often and every time I'd wished I'd tried it too. I'd had his cock in my hand and no more than an inch from my mouth and at the very last second, had backed out, making Charley jack himself off instead. To this day I couldn't tell you how I had managed to stop after getting that close to doing something I'd really wanted to try. But all I told Charley in response was, "Yeah. I've thought about it too." Then Charley told me something that surprised me even more than the news that he and Barbara had been swingers.

"Then maybe you should have come to some of those parties with Barbara and me. A lot of those guys are bi."

Suddenly I knew what I might have unconsciously suspected. Charley was horny and hoping there was a chance I'd be interested in helping him out - and not with one of the little cuties around the apartment complex. Charley was hoping I'd help him out myself. The fifteen year interim was meaningless. He wanted me to finish what I'd started. There was something else I understood too. Charley was making the assumption that my interest had increased over the years based on the fact that his had. He'd had an opportunity to experiment with other bi guys, had liked the experience, and since I'd been the one with the more avid interest in bi sex back then, he was assuming that I had to be more interested still. As much as I hated to admit it, even to myself, he was right. While I had yet to suck my first cock, there wasn't one anywhere in the world I'd rather start with than Charley's.

But first I wanted to learn a little more about what Charley had been up to. "So tell me. How many of those bi guys did you try out?"

He looked at me, his face twisting through a few looks, and finally in a sheepish manner, he told me, "Two. And one of them said he liked to do some of that pee stuff that you used to like. But we couldn't do it at the party and right after that Barbara discovered she was pregnant, and we never went to any more parties."

The "pee stuff" he was referring to was something I'd gotten into probably before I could remember. I've heard my mom and aunts say several times that they'd never seen or heard of a baby that enjoyed his wet diapers as much as I did; that after my diapers were wet that I'd try to hide it from them so they wouldn't change me and that as I got older, it had taken them years to figure out I wasn't a bedwetter and didn't need diapers. That was true. I always wet them as soon as my mom put one on me and slept in it. Of course it was soaked by the time I got up the next morning and my folks assumed I was a bedwetter. I remember my mom was really pissed when she found out I'd had her fooled all that time, but for some reason my dad thought it was funny and because he thought my playing a joke on them was so funny, I think he caught more flak for the whole thing than I did.

I was probably around nine or ten when my folks took my diapers away and I quit wetting the bed at night. But a few years later, when puberty began, I was already finding new and different ways to wet myself. Eventually, when Charley, my neighbor and best friend, and I began experimenting with masturbation and searching for new and exciting ways to beat our meat, I let Charley in on my piss play secrets. He'd known me from back when I was often still in diapers when he came over to play in the morning, and the fact that he'd never teased me about it was what had sparked our friendship. Nor was he surprised that I continued to have a fascination with piss into our teens. Charley wasn't nearly as excited by pissing games as I was, but he'd been happy to shower me with his piss and that, plus my attire and the beer we'd had to drink, had led to me almost sucking his cock. However, after that weekend, we'd both played it pretty straight. Charley had no idea that I'd continued to enjoy wetting myself or some of the other piss tricks I enjoyed over the last fifteen year. It was a guess on his part - and a good one. Pee play was one of those things that Gwen had enjoyed with me when we dated and during our first few years of marriage, but later threw in my face when she began calling me perverted.

I wasn't about to go into all that at the moment. My ex-wife wasn't nearly as important to the current situation as Charley's wife. "Charley," I began, "think about this for a minute while you still can. If Barbara didn't want you going to any of those parties you talked about to get laid without her, what makes you think she'd going to approve of you coming over here for me to fix you up with one of these gals that run around here?"

By then he'd had enough to drink - not that I was any too sober - that he finally laid it on the line, confirming my growing suspicion. He leered at me, dropped one hand in his lap to rub his crotch, and told me, "She probably wouldn't like that at all. But she said wouldn't mind if my old buddy Jim were to set me up with Wendy."

I wished I could have seen my face in a mirror. I had no idea if I was ashen faced or blushing bright red. But I felt flushed and my ears were buzzing. "Barbara knows about Wendy?" I finally managed to ask.

That lascivious grin grew bigger. "Has for years," he told me. "I told her all about that back before we got married. When her mom began coming up with these god-awful plans for a wedding, we joked about having Wendy as one of the bridesmaids."

Now I was really feeling flushed. "And . . . the other stuff?"

He nodded. "I didn't keep any secrets from her - and neither did Gwen. Right after y'all split up Gwen came by our place to return a dress she'd borrowed and she and Barbara got to talking and Gwen told her everything. She began by saying that if she'd left the dress with you, that you'd have been wearing it. When Barb didn't seem surprised, Gwen went into details. I'd sort of guessed you'd enjoyed being Wendy way too much to quit, but I was surprised to find out you still did all the other stuff too."

I thought about all the conversations I'd had with Charley over the last year and realized that in almost every one of them, he'd given me some sort of hint or opening that I could have told him about what I was doing with all my free time. But how do you tell another man, even if he is your best friend, that you love being a sissy and that you fantasize about sucking his cock? However I had told Gwen, and Gwen had told Barbara, and Barbara - unless Charley was lying - was okay with Charley spending some time with Wendy. It was scary as hell and a dream come true, all at the same time.

My heart was pounding in my chest. I was having a hard time getting my breath. And I had no idea what to say or do next. Fortunately, although he was definitely the drunker of the two of us, Charley did. "Why don't you get dressed?" he suggested.

After a second or so for me to realize what he meant, I nodded and moved slowly toward the bedroom, glad to have a chance to get away for a moment and think. I was almost out of Charley's sight when he hollered, "If you want to wear a diaper, that's okay too. Barbara said I might as well get used to changing them."

I had to sit on the edge of my bed and think. If Charley knew I still liked to wear diapers, then Gwen really must have told them everything. My first thought as I looked at myself in the dresser mirror was, how ironic. When Charley had called to say his mother-in-law was coming in and he wanted to visit for a couple of days, I'd thought it might be good to take a break and not dress as a sissy again that weekend, like I had for every weekend since the divorce. I'd made a point to hide all the things that might have given away that side of me and then it turns out that Charley had come here with the goal of spending time with me not as his buddy Jim, but as sissy Wendy and wanting me to "finish what I'd started."

Maybe I should tell you more about how that started before I tell you how we finished.

Charley has a sister that's a year younger than Charley and me. Back when we were fifteen, Adele was fourteen and just beginning to develop and of course we took notice. I'm not sure what started the conversation about Adele's new interest in wearing sexier lingerie, and it doesn't really matter. What's important is that we both concluded that if girls wore sexy under-things, that it had to mean they were interested in sex. Then a few weeks before that weekend we got drunk together, we were horsing around and Charley dared me to put on some of Adele's things that she'd left in the bathroom. For reasons I can't explain, I was already wishing there was some way I could try on the clothes before Charley made the dare and with that as my excuse, I gladly dressed up in her clothes. We joked around with me dressed like that for an hour or so and by the time I put my clothes back on, I was hard as a rock. I'd gotten a huge amount of sexual excitement dressing in girl's clothes and pretending to be some hot young slut that had just moved into the neighborhood that was trying to get Charley's attention. I'd been successful because Charley's prick had been as hard as mine.

I'd always liked wearing my hair long and it's a reddish-blond color. Not long after that incident, Charley and I had stopped to eat burgers and he'd pointed at the sign in the store, telling me that the next time I dressed in Adele's clothes, I should fix my hair like the girl in the picture and we could call me, "Wendy."

That same night I'd gone home and tried doing my hair that way just to see, and I can remember wishing that I had lingerie to wear. I'd also begun to wonder what it would be like to have sex with another guy. Like every other boy, I'd checked out the other guy's pricks in gym class. Now all of a sudden I was wondering how big they got when they were hard. Charley and I had jacked off together so I knew that there was a difference. Charley's prick was bigger than mine but barely doubled in size when it got hard. Mine was much smaller soft, but grew to three times that size when hard. So suddenly I'm looking at all those gym class cocks again and thinking about fondling each of them to make them hard.

The opportunity to actually hold another cock besides my own didn't occur until that weekend when Charley and I got his college age neighbor to buy us a case of beer to drink while Charley's mom and dad were out of town and Adele was gone over to a friend's house. By the time we'd finished our second beer, we were both buzzed. We were sitting outside on Charley's patio and when Charley got up to piss off the edge into the bushes, I'd cut loose in my shorts, deciding it was a good time to let Charley know how much fun pee play could be. Then later, when we decided it was time to move the party indoors, Charley insisted I should clean up and since I didn't have a change of clothes with me, I should wear Adele's things. By then we were pretty wasted and it had sounded like a good idea. I'd gone to her room, dressed in her clothes, and fixed my hair like `Wendy' and that was how I stayed dressed for two days, going through several changes of Adele's things, wearing dresses or blouses and skirts during the day and nightgowns at night. It was the morning of the second day when we'd come so close to that event that Charley now wanted me to finish.

Previously, I'd demonstrated to Charley how I could lay in the bottom of the bathtub and piss all over myself. Charley had offered to pee on me too, and while I really had wanted him too, I'd declined. When we woke up that second morning, we were both still drunk from finishing the last of the beer around 3 am. We both needed to pee and Charley dared me to wet the panties and nightgown I had on. So I did. I pissed in the panties and then took my prick out and wet the front of the nightie. Again Charley offered to add his piss to my wetness and this time I accepted, expecting him to wet the front of the gown and the panties I had on. However the first blast of piss hit me in the cheek.

I told him I didn't want him to do it any more and he complained that he'd barely started pissing and promised he wouldn't pee in my face again. When I told him I didn't trust him, he took his hand off his prick, pushed it out at me, and told me, "Then you aim it."

The only way I could do that was to take it in my hand and for some reason, since all I was doing was aiming his piss for him, that didn't seem wrong to me. But once I had hold of his cock and it began to swell, I realized what I was doing was much more than letting a buddy relieve his bladder. When Charley was fully hard, I began to slowly stroke his dick much like I would my own. I was still on my knees in front of him and as he edged closer, I held my position, until his cock was inches from my mouth. I might very well have slid it between my lips as I was moving on some sort of hypnotic trance, mesmerized by the turgid prick in my hand. Then Charley, sure I was about to suck it for him, broke the spell by telling me, "Yeah, Wendy, suck that big prick."

That was all it took for me to realize what I was about to do and stop myself. I continued to dress as Wendy for most of the day and a few times Charley teased me about how I could be the perfect boyfriend and girlfriend all rolled into one if I would like to try it, but it didn't happen. After that weekend, we never mentioned it again, I never wore Adele's things again when I visited Charley, and Charley never asked me to. We continued to spend the night at each other's houses until after we graduated from high school and never once did I suggest we try any sort of pee play together. While I'm sure we both masturbated as often as any other teens, we didn't do it again in front of each other. Now, fifteen years later, with both of us grown, we were bringing it all up again. We'd both been having the same sexual fantasy for all these years . . . .

From the boxes and bags that were hidden in the bedroom closet, bathroom, and under my bed, I gathered the things I needed and put them back in the places where they were normally kept - like the wig and wig-head that normally sat on my dresser next to my makeup tray. I refilled the top drawer of my dresser with diapers - both cloth and disposable - and the booster pads I wore with the disposables, and the plastic panties I wore with the cloth diapers. All my lingerie was returned to its rightful places, and the skirts, blouses, and dresses that I'd hidden in suitcases were re-hung in my closet. I spent a good twenty minutes or so getting everything back where it belonged before I began to pick out and put on the lingerie I knew Charley would expect me to wear for what would happen next.

I thought about trying to recreate the exact look that he probably remembered from when I'd used Adele's things, including the Wendy' style hairdo. However I'd learned a lot in the intervening fifteen years and it hadn't all been from teachers or professors. Surprisingly, Gwen had been a big help in teaching Wendy' much of the things a girl should know about appearance. When I'd first told her about that side of me, she'd been hesitant but then had become eagerly involved, taking my feminization on as a personal project. She'd refused to let me come to bed that way, but had enjoyed having `Wendy' as a girlfriend, taking me with her on shopping trips and one vacation that I will never forget.

A story in itself, we took a whole month touring in a rented RV and Gwen made me stay dressed as Wendy for the entire time, even allowing me to come to bed that way. In addition, the first week on the road, when I commented about the bathroom, and how it was nice to have one along so you didn't have to wait, but that you still had to pull over if you were driving, Gwen came up with a solution.

"You like everything else about being a sissy. I'm surprised you haven't thought about wearing diapers again. They might make some of your `Wendy' things fit better."

I'd been surprised too. What had made me mention the bathroom had been the need to pee and seeing a sign about a rest area coming up in five miles. We'd gotten into some pee play the first night out and had needed to drive with the vents open the next day to air out the urine smell because we'd gotten a little carried away, soaking one mattress and an area of the floor rug. So we'd refrained from doing anything like that again. But her mentioning diapers had gotten me thinking about how much I had enjoyed them at one time. "It would probably feel great to have on a diaper and wet it while we drove," I'd told her. "You wouldn't mind if I tried it?"

"It'd make a whole lot more sense than some of the other things I've seen you wet," she answered and we'd continued to discuss it off and on for the rest of the day. As luck would have it, when we'd pulled off the interstate at the town where we planned to spend a couple of days, there'd been a drugstore on the corner of the first traffic light we hit. "Pull in there if you really want to try it," she'd suggested and I'd known exactly what she'd meant.

For the last three weeks of our vacation, `Wendy' was diapered 24/7, as they like to say today, and Gwen tried it several times too. To my way of thinking, that vacation was more like a honeymoon than any honeymoon I've ever heard or read about. When we got home, we kept much of it going. With friends and neighbors and relatives in and about, we couldn't have me dressed as Wendy all the time as we had on vacation, or wearing diapers very often either, yet we still managed to enjoy it with some degree of regularity. As I've said, except for that vacation, Gwen wouldn't let me come to bed in lingerie, except on rare occasions, and I couldn't make love to her dressed that way, but she didn't mind if I wore a diaper and feminine t-shirt like a little girl. According to the marriage counselor that we tried - obviously unsuccessfully - a lot of it had to do with Gwen's desire to have children.

Since I'm being so honest about that part of my life, let me tell you that Charley and I both had that problem in common - wives that wanted children and we couldn't help. In Charley's case, they found an anonymous sperm donor. In my case, Gwen decided to find another man - and not just for the night.

From the first time we'd made love, Gwen had made fun of my widdle wee-wee' and had always done it in a joking way, followed by assuring me it was plenty big enough to make her happy and how the way I used my tongue more than made up for any shortages elsewhere. But years later, when we'd been married a while and she wanted to have kids and we weren't having any luck, and unlike Charley, my sperm count was normal, Gwen decided the problem was that my dick was too short to get the sperm in place. Then she concluded that my little guys' were probably all sissies like me and afraid to swim. "That's why there's always so much for you to lick up," she'd told me one night as I licked her pussy after sex. "You don't get it up there very far to begin with and then those little sissy sperm cells just go with the flow instead of swimming upstream like they're supposed to."

I hadn't been able to argue that at all. I'd suggested we try artificial insemination. She'd suggested a divorce and finding a real' man. I wasn't thinking about getting her pregnant, as Charley and Barbara had been when they invited us to a swing party. My thought was that it would be a way for her to enjoy a real' man occasionally and still maintain our marriage. Instead, the suggestion had been taken the wrong way. Immediately she'd concluded that it was an excuse for me to act like a sissy with other men, an allegation she'd made a few times and hinted at often. I'd admitted that I'd fantasized about Charley's cock but had always sworn that it was only a fantasy and not something I ever intended to make happen. But now, as I dressed in sexy lingerie for Charley, I wondered if maybe she'd known me better than I knew myself.

I debated briefly about the diapers. Charley had said it was okay. That was Charley. He'd said exactly the same thing when we'd been in elementary school and he discovered I wore diapers to bed at night. He'd also hinted that he might like to learn to change them while he was here. That could be a lot of fun. But to begin with, I wanted to be as much like the Wendy' he remembered from our teens. Then it hit me, in a humorous way, that at least once a week for fifteen years, I'd thought about the morning when I'd come so close to sucking Charley. Yet when I went to pick out a nightie to wear, I couldn't remember what color Adele's nightgown had been. All those details might have been recallable in the first few years, but lately they'd all been distilled down to images of Charley's cock, standing proudly in my face, and what an ignorant asshole I'd been for not taking it in my mouth like we'd both wanted. The more I thought about how close I was to correcting that mistake, the harder my widdle wee-wee' got in my panties.

I half expected Charley to be naked when I walked back in the living room. He was still fully dressed and still sitting at the pass-thru bar nursing another beer. I wasn't sure if his stunned reaction when he saw me was good or bad.

Finally, after gawking for several seconds that seemed much longer to me, he half whispered, more like he was thinking aloud than talking to me, "You look like a woman."

I had to laugh. "Well isn't that what you expected?" He'd made it plain that the real purpose of his visit was to see `Wendy' and that he had Barbara's approval for anything that happened.

He stammered, "Uh . . . yeah . . . sort of . . . but . . . you look . . . I don't remember you looking so good."

I found his confusion humorous. I thought I knew what he meant - that I looked a lot better than he remembered - but I had to tease him. "If you remember me looking bad, I don't understand why you'd want to see me again that way?"

"I remember you looking like a guy in my sister's clothes," he explained. "Now you look like a sexy woman. A real woman. If I didn't know you, I wouldn't know you."

I figured that was about as close to the compliment that I was looking for as I was going to get. "Thank you. I'm glad you approve." Then I took a deep breath and confessed, "I've wanted to dress like this for you many times."

"That's kind of what Gwen told us. I was surprised but Barbara said she'd always suspected you still had a crush on me."

I smiled at his choice of words. I hadn't heard anyone speak of a `crush' since we'd been in school together. "Looks like she was right," I told him in as seductive a voice as possible. "I always considered it a fantasy that would never happen. I know a lot of men go through their whole lives with fantasies they never act out. I thought of you as one of them." Then I batted my eyes coyly. "Until now."

Charley didn't know what to do next and I had less experience than he had. But when he told me how hot I looked and how it was making him hard, I replied, "You'll have to show me."

That put it on the line. It was time for action. Charley slid off the barstool and reached for his belt. Then he stopped and smiled at me. "The last time we did this, you were trying to act like a slut and you undressed me so I could pee."

I can be slow, but not that slow. I knew he wanted me to undress him and I was more than happy to, moving to take off his shirt first. When I had him bare to the waist, I dropped to me knees, helping him off with his shoes, `accidently' letting my cheek or forehead brush the front of his jeans a few times, and then in a slow, tantalizing manner, began with his belt buckle and the fly of his jeans. I was amazed when I discovered he had on panties.

"Barbara's idea," he told me. "She thought of me as being a present to you so she decided to gift-wrap it in her panties. She said if you do a good job, I should let you keep them as a souvenir of our doing it."

At the same time that I helped him step out of his jeans, I rubbed my face in the front of the panties, nibbling on the bulge much like I was eating an ear of corn, one kernel at a time. Then, at long last, I freed that cock I'd thought about so often, admired it once again from inches away, and then made it disappear, fighting the urge to gag as it slid past the opening to my throat. Much slower, I let it all slide back out, and then began kissing and licking and sucking and making every wish come true for both of us. It would seem that Charley hadn't been exaggerating about a long sexual dry spell. I didn't try to fool myself into thinking it was my cock sucking talent that made Charley fill my mouth with hot jism so quickly.

But I didn't stop. I continued sucking as his cock spasmed, wanting every creamy drop of cum that I'd longed to taste. When my siphoning on his overly sensitive spent prick became too much for him, Charley had to push me away or I'd have stayed where I was, on my knees between his legs, with his cock in my mouth, savoring the unique taste of his cum, until . . . well there's no way of telling. One thing for sure, I wasn't going to stop until he stopped me. Then, just to be sure he knew I had no intention of letting this be a one time thing, I looked up at him, almost pleading, swallowed most of his jism, and asked, "Can you cum again?"

Charley grinned, pulled me to my feet, and held me tight against him. For a moment, I thought he was going to kiss me and I wasn't sure how I'd feel about that. For some reason, my sucking his cock had seemed like the most natural thing in the world for me to do - like some people have a way with kids and others with animals. Charley's cock in my mouth had been a natural talent that I'd used. But two guys kissing - that seemed - queer . . . Go figure.

But I'd never pulled the panties off him, merely pushed the waist down to expose his cock and the moment it was freed, I'd engulfed it. Before pulling me to my feet, Charley had pulled the panties back over his prick, probably to keep it away from my ravenous mouth. Now his panty covered cock was rubbing on my panty covered cock and it felt wonderful. One of my unfulfilled fantasies with Gwen had been for us to do things like that all the time; cuddle together in lingerie, letting the sensual material stimulate our bodies. Combined with the arousal I'd gotten from sucking Charley's cock and finally being able to swallow his load, feeling his panty covered prick against mine was too much. I began shooting uncontrollably in my panties and I'm sure it was enough to soak through and moisten Charley's too.

I was embarrassed to lose control like that, but it didn't bother Charley at all. "You're one hot little bitch," he told me. "I was hoping to help you with that."

"You mean . . ."

He nodded. "Yeah. I've thought about it for years. I was hoping that if you and Gwen went to one of those parties with us, I'd get a chance to try some of this stuff with you. But when you didn't go, and I had a chance, I did it. I love Barbara and wouldn't want to ever give her up, but sex with a guy can be fun too."

I put my head on Charley's shoulder, wondering if it was wrong to hope that the baby didn't come any time soon and that after it did, that Barbara's mom would want to hang around for a while. If I'd known what Charley had wanted, and that I was going to get divorced anyway, I'd have gladly gone to one of those parties by myself, it that was allowed. It was music to my ears to hear and know that Charley had wanted me to suck him for as long as I'd wanted to do it. Better yet, Barbara, for whatever reasons she might have, approved of it. That meant the next fifteen years wouldn't be the waste of time that the last fifteen had been. I licked my lips, tasting the remnants of his cock and cum and the lipstick that made it all the more sensual and thought it couldn't get any better than this. But it could.

"I need to pee again," Charley whispered in my ear. "Any chance you might want to help me with that?"

There was no chance at all. To me it was a 100% sure thing and I told him so, adding, "And I don't just want to help. I want every damn drop!"

Hand in hand, we walked into my bedroom and Charley was surprised when I pulled him toward my bed instead of the bathroom. "My mattress is protected," I whispered, then laid in the middle of the bed for him to shower me. It was his turn to surprise me when he lay down beside me.

"In that case, we can both get wet," he said pulling out his prick and aiming it up in the air. Soon he had a strong stream going, arching up to splatter back on both of us. After the front of my nightie was soaked, and before the sheets got too wet, I moved down to take his cock in my mouth and gratefully swallowed what was left of his precious piss. Long after he was done pissing, his cock was still in my mouth and I was finding out for myself the answer to the question, "Can you cum again?" It took longer this time, which was fine by me. As much as I loved his cum, it meant I'd have to quit sucking for a while and I loved having that prick in my mouth more than anything. I paused a few times when I knew he was close, prolonging his pleasure as well as mine, and then at last, when he announced again that he was going to cum, I nodded without taking my mouth off him and increased the suction. His balls all but disappeared and I wondered if it had anything to do with the vacuum I was applying to his dick. Then that beautiful piece of man meat was erupting again, and all my thoughts were on how absolutely awesome it was to orally service a man. Never in my life had I felt anything as exciting as Charley's cock in my hand, the taste of it on my lips and tongue, and the satisfaction I felt when he flooded my mouth with his cum.

Charley felt much the same and he was anxious to show me. He pulled up the hem of my soggy nightie and pushed down the front of my panties, the same way that I'd done his, and after fondling my piss soaked prick for a minute, slid down to take it in his mouth. Then he gave me a demonstration of the skills he'd acquired at those parties, showing me that he knew his way around a stiff prick and how to get those cum laden balls of mine to let go the jism he longed to taste.

After resting a bit, we had a decision to make. "Unless you want to sleep in a wet bed," I told him. "We need to clean up and change the sheets."

"Wet bed's fine with me," he answered. "I'd planned to wet it myself if nothing else worked."

That confused me so he explained that he and Barb had discussed different ways that Charley could get me to admit my fantasies. Plan `A' had been to have a few beers and get me talking about when we'd been teens and as it had turned out, that plan had worked like a charm. However, if it hadn't, Charley had intended to let me discover he'd been wearing panties, and if that hadn't worked, or if I had passed out or something, he'd planned to crawl in bed with me and wet the bed and let me wake up to discover him sleeping with me in panties and the bed soaked with piss. "And if that hadn't worked," he concluded, "I was going to throw you down, suck your cock, and you could go to hell if you didn't like it."

I had to laugh. "You have no idea how many times I thought about doing the same thing to you. I'll bet over the years I've thought up a hundred different scenarios where I'd find some way to trick you into letting me suck you off or talk you into it or we'd get drunk together and you'd pass out and I'd suck you while you were out or something."

"Well I haven't always been honest with you, especially back when we were teens. When you told me about wetting your diapers as a kid for fun, I tried making diapers out of bath towels and wetting them and wetting the bed like you did and all that stuff but I never told you about it. And the reason I wanted you to dress in Adele's underwear was because I'd been doing it, but I never admitted that. And believe me, I wanted to suck your cock as much or more than you wanted to suck mine, but I never admitted that either. Then when we got a little older and started dating and stuff, I still thought about it, but I never tried any of it again until we started going to those parties."

"So you really started wearing panties and pissing again at those parties?"

He shook his head. "No. But it got me thinking about it again - a lot. I was determined that if I ever did any of that sort of thing, I was going to do it with you. Then when Gwen told Barb you were still doing all that - and more - I damn near drove over here that same night. But Barb said to settle down and think it through and do it right or I might scare you so much we'd never get together."

I smiled up at him and slowly began to caress his cock through the wet material of his panties. "Remind me to tell that wonderful wife of yours how much I owe her and I mean big time. She's been a big help and any time you need help, you know where to cum." Then I opened my mouth in a perfect circle, about the diameter of his dick so that he knew exactly what I meant.

My last waking thought, as I drifted off to sleep that night, my head on Charley's thigh, and his pretty prick in my mouth, was wondering how many other guys like Charley there might be that needed `Wendy's' help.

I was so happy I even thought about writing Gwen a thank you note. I'm sure she hadn't had my pleasure in mind, but leaving me and then giving away my secrets, had made all my dreams come true.

Comments appreciated: amber_fountaine@hotmail.com

Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate