Allison's Story

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.

This is the first in a series of short stories that have been related to me over the last 35+ years that I've been in contact with others that enjoy the same things that I do. Every time I've met or corresponded with someone, I've made a point to ask how they developed their interest and I've used combinations of those stories as the basis for much of what I've previously written. However that was when I had a lot more time to do so. With less time available to me, for this series I'll relate the more interesting stories as I remember them. Since I change the names anyway, what I'll do here is put them in alphabetical order rather than by chapter.

Allison's Story

as told by Amber Fountaine

My second wife, Denise, and I were both well past 40 when we met. She'd been married for nearly twenty years to her first husband and three years to her second. I'd been married once, to a woman with two kids, and we'd had none of our own. In comparing notes about our previous mates - we'd really not gone into much detail - we'd both agreed that our sex lives with our first partners had been fantastic, but other problems had developed. My first wife had been awesome in the bedroom, but had a drinking problem she wouldn't face. Denise said her first husband had been a fantastic lover and tried to prove it to every woman he met. She told me her second husband had shown more than a little fondness for her daughter Anne and that was one reason that marriage had failed. She also commented that their sex life hadn't been that hot, and she supposed he really liked younger women, something her first husband had also done. With those hints in mind, I knew being faithful and not showing any interest in her daughter would be very important in our relationship.

Being faithful was easy enough. I'd never been the kind to cheat. What had made my first marriage to Cheryl so fantastic was my ex enjoyed my fetish for wearing women's clothing, especially lingerie. Any weekend her ex had her kids, she had me dressed up as Allison from the moment the kids were out the door. She went as far as showing me off to a few of her girlfriends, and often teased me about loaning me out to them as a maid. One of her friends would tease me about taking me home to help her satisfy her husband, telling me that he was always after her to suck his cock and she was sure I could do a fantastic job. I'd never had any fantasies about doing that prior to the ladies suggestive comments, but as my ex and her friend tantalized me with tales about how big his cock was and how much cum he'd shoot in my mouth, I began to think about what it would be like to really do it. Eventually Cheryl got me to admit I'd like to try it, and for a while, I was sure she was going to make it happen. Nothing ever came of it though and by the time that we divorced, I was almost begging for the experience.

Once I was divorced I had a serious choice to make and one I thought about long and hard before I made it. I could either continue with my cross-dressing, and let that follow the course of my fantasies, or give it up altogether. I knew it had to be one or the other and decided, with the help of a new job, to purge "Allison" and my feminine wardrobe.

Then a couple of years later I met Denise and we seemed to hit it off. When our relationship became sexual, it was a far cry from what I'd experienced with Cheryl, but I wrote it off to Cheryl being exceptional and Denise to being the ordinary sort of sex that I imagined most people enjoyed. What made it work for me was that we both traveled for our jobs. I knew I'd have several nights a month when Denise would be gone and I'd dress up in some of her lingerie, maybe add some makeup, and masturbate like crazy while fantasizing about "Allison" the cum slut. We'd been married almost five years before I discovered Denise wasn't happy about our love life either.

It was right after a typical night of sex. I fondled her tits for a few minutes. She sucked my cock for a few minutes. I ate her pussy for a few minutes. We fucked for a few minutes. Thirty minutes after we'd started, we'd have been smoking a cigarette if either of us still smoked. Then she caught me off guard.

"Al, you told me one time that you thought your sex life with Cheryl was great. Do you think ours is?"

I'm no dummy. That was a question that could lead to a fight or hurt feelings that might never be healed. "You're not Cheryl. It's different with us. You never deny me and always satisfy me."

She giggled, which surprised me. "Since when did you aspire to be a politician?"

For lack of a better response, I kissed her. Then I began to wonder what had caused her to ask that question. Had I said or done something to make her think I wasn't happy? Or . . . With some trepidation, I asked, "Do I satisfy you?"

There was a moment of silence that lasted too long for me to expect any other answer. "Well . . . not really."

How do you answer something like that? I didn't know what to say. After a moment I asked, "Is there anything you'd like me to do?"

"Eat me."

I could tell she was serious and began immediately, wondering what had changed her mind about that. Back when we'd been dating, on one of our early love-making sessions, I'd licked her pussy after we fucked and her reaction had been . . . well, upset is putting it mildly. She'd told me that it was nasty and that she couldn't understand why any man would want to do that since she was full of my cum. I tried to make light of it, explaining that she'd sucked my cock and eaten my cum and how I couldn't very well expect her to do that if I wasn't willing to taste my own cum too. She'd calmed down, but had never asked me to do it again.

With Cheryl, it had been something I'd been expected to do. Any time I left cum in her pussy it was my job to clean it out. With it of course came all the teasing about 'Allison' being a cum slut. To tell the truth, it had been something I'd quickly learned to enjoy and look forward to. But where it was something that had turned Cheryl on, it had just the opposite effect on Denise.

So you can imagine my surprise when five years later, she suddenly asked me to do it. From the way she moaned and dug her fingernails in the back of my scalp, I knew she enjoyed it. Her next comment, a few minutes later, let me know how much she'd enjoyed it, and also, how pitiful our sex life had become.

"Did you know that's the first time you've given me an orgasm since before we were married?"

I was crushed. "What can I do? Tell me what you want and I'll be happy to do it. Anything," I pleaded.

She laughed. "That's taking an awfully big risk there - saying 'anything.' You have no idea what I might want."

I really didn't care. We were so compatible in every other area that I couldn't imagine not spending the rest of my life with her. If she'd suddenly said she wanted to wear high-heeled boots and lash me with a whip I'd have probably gone for it. Instead she told me, "Well, uh, we could try some of the toys I play with when you're out of town."

That was almost as big a shock as her telling me to eat her. I'd had no idea she owned any sex toys and played with them while I was gone like I played with myself when she was gone. "Sure," I told her. "I'll be happy to. Cheryl used to have some we used sometimes. I don't see anything wrong with that at all." With very little more encouragement, she got her 'toy box' out of the closet and that's when I discovered the real reason I wasn't making her happy. Everything in her toy box looked as big as my wrist and almost as long as my arm.

I looked at the dildo she'd called her favorite and marveled at its size. It was about the size of an empty paper towel roll, only bigger. It was almost a foot long and two inches across. "Can you really fit that in you?" I asked. The dildo Cheryl had used - including on me a few times - was about two-thirds that size and I'd thought it huge.

Her response was to laugh again. "Of course," she told me. "I've had two kids remember." Then she let me begin to understand her real problem with me. "Besides, Jake was that big when he got hard."

Jake was her first husband; the one she'd said had been such a good lover. My dick wasn't close to half the size of her ex. I got confirmation on my suspicion when I asked, "What about your second husband?"

"About your size," she said, "Maybe a little bigger."

Well crap! Her second husband had been the one she'd said hadn't been all that good in bed. I blurted out what I was thinking. "I'm surprised you married me."

Suddenly she realized she'd hurt me. "You have a lot going for you that neither of them ever did. Jake was a two-timing bastard and still is. And Gary was more interested in Anne than in me. You're the nicest man I've ever met."

I know she'd meant it as a compliment, but suddenly being "nice" sounded like the biggest put-down in the world. I was a "nice" guy but a lousy lover. Then something she'd said caught my attention. "What makes you say Jake is still a two-timing bastard? I thought you never heard from him - only through the kids."

"He called me a couple of weeks ago - about Anne and her boyfriend. I told you they'd broken up and Anne is pregnant. Jake's married again but that didn't stop him from offering to treat me to a weekend with 'Big Jake'. That's what he likes to call his cock. When I asked him about his wife, he told me she wasn't a selfish bitch about things like that like I'd been. Can you imagine?"

Yeah, I could. I'd met Jake once when their son graduated from college. I could easily imagine Jake with a cock the size of that dildo fucking the woman that was now my wife, that huge thing sliding in and out of her pussy, and the effect of my imagination didn't go un-noticed.

"My God! You're getting hard again just thinking about it. Well forget it. I'm not doing it."

I hadn't been about to suggest that at all. I also knew this conversation didn't just happen accidently. "But you want to don't you?"

Bulls-eye! She jumped up from the bed, grabbing her robe and told me, "I don't want to talk about it." But from the flushed look about her, I knew it wasn't the big dildo I was holding in my hand that she wanted to play with. She wanted the real thing. And she did want to talk about it. But she'd approach it each time in a round-about way, beginning a couple of nights later.

When she made it clear she was in the mood for sex, I began in the usual way, then suggested she get her toys out and show me how she'd like me to use them on her. She hesitated just long enough to make it look like she wasn't thrilled by my suggestion and then gleefully got out her toy box. There was a funny looking one that I'd never seen and I was amazed when she told me she liked to put that one in her ass. We'd never included any kind of ass play in our sex and that sure changed in a hurry. The next time we had sex, I had the dildo, which I'd started calling "Big Jake" in her pussy and she eagerly accepted the idea of taking my little cock in her ass at the same time. The orgasm she had was amazing to me. Then when I was ready to cum, I pulled out the dildo and fucked her pussy and was again amazed that she could tighten up on my much smaller prick.

The next time we built on the previous session and this time, after I'd cum in her, instead of licking her clean, which she now seemed to love, I reinserted the dildo which she loved even more. Then, for reasons I'm not sure I understood, I pulled the dildo out and began to lick the cum off it. Maybe I wanted her to know about my fantasies.

She watched in awe for a bit and then asked, "Have you ever sucked a real one?"

"No. Never," I told her hastily.

"But you want to don't you," she told me, using my words from the previous week.

I wasn't about to admit I'd thought about it for years. Instead I did the same thing she'd done, again using each other's words. "I don't want to talk about it," I told her, trying to keep a straight face.

She couldn't keep a straight face either. We wound up rolling together laughing. Then she reminded me, "You told me one time you did."

I knew immediately what she was talking about. About a week before we were married, we were talking about sex after we'd had sex and I'd mentioned that Cheryl had dressed me as a woman a few times. I didn't tell her how often or how much I'd enjoyed it. I'd been testing her reaction and she'd asked, "Why would you want to do that? Do you want to have sex with a man?"

I'd admitted that I'd thought about it, telling her that I thought most men thought about it, no matter what they might say, but that I'd never done it and her response had been something to the effect that she thought it was sick - not at all the response I'd hoped for. Then a few weeks later, while packing for our short honeymoon, she'd received two nightgowns that were almost identical as presents from her friends at work and was holding them both at the same time, as if deciding which one to take. Joking, I'd asked, "Is one of those for me?"

"Don't tell me I've married a pervert," she'd responded and I'd laughed it off. But that was then and this was now and she seemed to have a different attitude about a lot of things. It seemed like the perfect opportunity to test the water again.

"Yeah," I said, admitting that I'd had an urge to try sex with a guy. "I did. I was sure Cheryl was going to make it happen and I wanted it to happen. But that was a long time ago and under different circumstances. I don't have any desire to have man-to-man sex. But back when Cheryl dressed me as a woman, it was almost natural to think about doing things that a woman would do. I guess it had something to do with the sexy lingerie she had me wear."

Her reaction was more than I could have possibly hoped for. She thought about it for a minute or so, then jumped out of bed, pulling me with her. "Come here," she said, dragging me to her dresser. I was very familiar with her lingerie drawer and as it turned out, she'd suspected as much for a while. She pulled out a matching bra and panty set and a short nightie and in less than two minutes, had them on me with the bra stuffed with two pair of rolled up pantyhose. Then she sprayed me with a spritz of perfume and dabbed some lipstick on my lips. "What do you think?" she asked turning me toward the mirror.

I would have been overjoyed except for one thing. The outfit she'd put on me was exactly the same one I usually wore when she was out of town. It was too much of a coincidence. But that didn't keep my cock from responding.

"Never mind," she told me, running her hand over the bulge in the nightie. "I can see for myself. Now let's try it again." She led me back to the bed, and after lying on her back with her legs splayed and knees bent, she took Big Jake and eased it back inside her. After moving it in and out a few times, she pulled it out and reversed it, holding it against her mons so that it looked as if she had a huge cock. "Okay sweetie. Let's see what those pretty red lips can do now."

I hadn't had a dildo in my mouth since I'd sucked Cheryl's for her. This one was much bigger and I wasn't sure I could do it, but somehow I did - at least the end of it. I'd have choked to death if I'd tried to swallow even half of it.

"I think someone wants to try the real thing as much as I do," she commented - the first time she'd admitted in any way that she really wanted to have sex with her ex.

That evening with "Allison" was followed by several others and during them I learned that she'd suspected for over a year that I'd been wearing her lingerie. She'd been laying traps for me for months, each time folding her things a little bit different and I'd confirmed her suspicions for sure when I'd forgotten to readjust the shoulder straps of her bra when I put it back. "And you really should have rinsed the cum stain out of the lavender nightie," she told me, but she wasn't upset about it.

We played like that for about a month before she asked, "Allison, If Jake would let you suck his cock, would you do it?"

More than anything, I wanted to see a real cock that big. And yes, I really wanted to suck it if I got that close to it. But I hedged. "If you want me to."

She laughed, knowing me well enough to know I just couldn't bring myself to admit it. "The only way we can make it happen is if we let him fuck me. Are you okay with that?"

I was and I wasn't. I was taking a chance of loosing her. But at the same time I knew that what we'd been doing, playing with 'Big Jake' the dildo, wouldn't keep her satisfied for long. With or without my okay, she would eventually fuck her ex. "Yeah," I told her. "Let's do it."

I wasn't invited to their first sexual reunion. In fact, I didn't even know it was going to happen. I came home one evening and found her already in bed. "Put on your 'Allison' things," she told me. "I have a surprise for you."

Quickly I did as told and when I climbed in bed with her, she whispered, "Jake left a few minutes ago and he left something for you." Then she flipped back the sheet and one look at her wet, puffy, pussy told me she'd been fucked and good. There was a huge cum stain on the sheet where some of his cum had already leaked out, but what was left was more than I'd ever put in her. As I licked up his cream, I tried to imagine what it would be like to have that much cum shot in my mouth. It was a very exciting thought. Allison was indeed becoming a cum slut.

Jake fucked Denise two more times before he agreed to let me be present and that was all he'd agree to. As to me sucking his cock or having any contact with him, he said he'd have to wait and see how it went. He didn't have a chance. Denise had once commented that Jake was such an animal that he'd fuck anything that looked female to him and Allison looked a lot better than that. Denise found a wig somewhere and when Jake showed up for our 3-some, Allison looked so hot that he never thought of me as another man.

Over the next six months, every one of the speculations that Denise and I had made came true. I'd told her that I thought all men at least think about sucking cock, even if they never do it. After a couple of months, Jake admitted he'd like to try sucking me and told us it "wasn't bad". And Denise's opinion that Jake was a two-timing bastard also proved out. Our 3-somes were awesome good fun for all of us, but it wasn't Jake's style. He tried to get Denise to meet him behind my back and to the surprise of both Denise and myself, he tried to get me to meet him behind Denise's back.

Then fate dropped a gift from heaven in our laps. A young lady that worked with Denise mentioned one Friday evening, when the girls all went out after work for drinks, that her boyfriend liked to wear her panties but his cock was so big it was almost impossible even when he was soft. It took a few of weeks for Denise to set up a 4-some. The guy turned out to be nearly as big as 'Big Jake' and I thought we all had a great time. We did it again a few times, but when her friend from work decided it was all too kinky for her, she dropped out. If she had any opinion of her former boyfriend, who we call 'Bonnie', moving in with us, I don't know nor do I care. What I do know is that Allison is one happy cum slut, Bonnie thinks he's died and gone to heaven, and Denise smiles more than she's ever smiled in her life.

Comments appreciated: amber_fountaine@hotmail.com