Amy’s Adventures in Cuckqueaning Ch. 1

I had been dating my girlfriend, Amy, for about 4 months when she finally confessed, she was a sexual deviant.

But first, let me give you a little context.

Amy was a sexy little number. She had shoulder length brown hair that she had dyed black, pale green eyes, and a slender body. She was 25 years old, about 5’4” tall, and weighed 121 lbs. She had a great figure with a nice bubble but from her time spent in the gym and a 34B bust, 24” waist, and 34” hips. She was one of those preppy goth chicks who liked the aesthetic but not really the lifestyle. She embodied the cute, sexy California girl vibe dressed up as goth chic. She lived in a house that she shared with four other “female” flat mates. One was a transgender woman, not that that has anything to do with this story.

I was two years older than her, 6’1, and 185 lbs. I had previously been in the Marine Corp but had transitioned to civilian life a few years ago. We lived in a suburb of Las Vegas and met during a fitness class at our local gym.

We quickly hit it off and to say I was smitten would be an understatement. I adored Amy, she was shy initially but bubbly once she opened up. She was sexy, but could pull off that innocent look that got my pulse racing. She had a banging body and a great personality; she was the whole package.

As we got to know each other, I learned she had previously experimented with other females when she was in the middle of her hardcore goth days in college, but she denied that she was bi-sexual or gay and instead claimed it was just a phase she went through during college. While she enjoyed the female body, she was more interested in men. I was smart enough not to ask for a lot of details at first.

When we finally had sex for the first time (that may be a story for another time), it was great, at least for me. Amy enjoyed it, but I was a little big for her small frame. Girth wise, not length. I know I’m not packing some sort of giant king snake down there, but I think I’m slightly above average at about 6 and ½ inches….anyway.

Amy was vocal, which I loved, and seemed to always focus on my pleasure. She was a great lay. She had been dropping hints for a few weeks about her needs and desires, but wouldn’t come out and say it because she was afraid it would scare me off. I assumed she was going to say she liked to be spanked, choked, or was into rough sex since she was what I would describe as a semi-goth. She first admitted she liked to be dominated, which I didn’t think was too taboo. It was so cute watching her admit that she liked being dominated. She was nervous, I guess, about how I was going to react. I patiently explained to her that all men were sexual deviants and that we suppressed our desires out of fear of scaring away our partners.

“I don’t believe I’ve ever been scared off by a woman’s fantasies, but I have seen it happen the other way around numerous times,” I reassured her.

After gauging my reaction to that news, she finally shared her big secret with me. Amy said, “I’m really into cuckqueaning. The idea of it makes me so horny and I always orgasm so hard when I’m thinking about it.”

I consider myself a pretty progressive guy, but I’ll be honest, I wasn’t sure what this meant. I knew ‘cuckolding’ was when a woman fucked other men in front of her male partner, but had never heard of cuckqueaning.

She explained that cuckqueaning was when a woman’s male partner has sex with another woman, preferably in her presence. It wasn’t just about sharing me with another woman, it was about being humiliated and degraded by being consensually cheated on with another woman. I know, I know….daddy issues right? At least that’s what I was thinking at first.

She elaborated, “I like the concept of being cheated on right in front of my face. The thought of my boyfriend becoming aroused by another woman, of him being tempted, and ultimately being lured into sex with her is extremely appealing to me.”

To say I was shocked was an understatement, but I quickly recovered as I realized what this opportunity might mean for me. I reassured her I was intrigued and ok with idea conceptually, but I was afraid it might damage our relationship and honestly wasn’t sure how to start the process even if I wanted to.

As Amy explained more of her fantasy to me, I became more and more turned on by the idea. We talked through a couple different scenarios including picking up a stranger in a bar, calling an old girlfriend, and using a sex worker. Ultimately, we decided to hire a sex worker off the internet for the first time so that she could accurately assess whether she enjoyed the experiment while ensuring that we had complete control of the situation.

We spent the next few days searching through online adds and finally found someone that we both agreed would work for our first foray into cuckqueaning, Mallory. Mallory was attractive, she had a tall, lithe frame with shorter auburn hair and green eyes.

Amy contacted Mallory, explained everything to her, and made all the arrangements.

The next Saturday Amy and I checked into a nice hotel located near downtown. Once we were all settled in, Amy texted Mallory the room number.

Mallory arrived about an hour later with a light rap on the door. She was wearing a beige short sleeve top, short black skirt, black stockings, and black leather boots. She was almost as tall as I was and seemed to have legs that went on for days. She was gorgeous and probably also in mid 20s or early 30s. “Kyle, I presume” she asked walking into the hotel suite’s entry foyer.

“Yes, and I’m guessing you are Mallory,” I stated.

She nodded and asked “Where is Amy?”

“She is waiting in the bedroom. I wanted to make sure we hit on a couple of things before we started. Amy wants to be humiliated and degraded by watching someone else have sex with me so feel free to taunt her and describe what is happening and how it feels. Amy and I have discussed this in detail and we have permission to do whatever we are comfortable with. There are condoms on the bedside table with lube if you need it and I’ve taken a pill to ensure I can go a couple of rounds. We have established a safe word, just in case anyone needs things to slow down or stop. It is ‘Zebra,’ so hopefully that won’t spontaneously come out in conversation.”

Mallory acknowledged the ‘rules,’ grabbed my hand, and proceeded to pull me towards the bedroom of the suite. She was pretty in person, not the greatest body one could find on a sex worker in Las Vegas, but she good enough that I’m sure she stayed pretty busy.

As we entered the bedroom, Mallory locked eyes with Amy. “Oh, there you are. Excited about the prospect of watching me devour your boyfriend and then give him the best fucking night of his life? You’ll be lucky if he even wants you after I’m done with him, after all, I’m a professional,” Mallory stated mockingly.

“You stay right there in the corner where you can watch everything, but absolutely no touching him or me unless I give you permission. Got it,” she asked?

“Yes,” Amy replied meekly.

Mallory turned her attention back towards me. She grabbed at my belt and in mere seconds had my pants around my ankles. She turned to make sure Amy could see her hand gently squeezing my quickly rising bulge. “Oh, looks like we have a nice little package here that is in need of unwrapping,” she said as she fished my rapidly hardening cock out of my boxer briefs. Her hands were slightly chilly, eliciting a little tremor from my body at the contact. “Don’t worry, I’ll warm you up in just a second,” she cooed.

Mallory dropped to her knees and pulled my boxer briefs down to join my jeans, which I quickly kicked both to the side and pulled of my t-shirt. I looked down as she wrapped her slender fingers, with their bright blue nail polish, around my cock and gave it a slight tug. Before I could say anything, she enveloped my cock in her pretty little mouth until her nose was pressed into my abdomen. “Uggggghhhh,” I moaned as I looked at her ruby red lipstick ringing the base of my now rock-hard cock as it fully expanded inside her warm, sucking mouth.

I looked over to see Amy watching intently as Mallory began to bob up and down on my shaft while cupping my balls and rolling them in her palm. Mallory was doing great and was easily taking my 6 and ½ inch schlong down her throat, though it reminded me of a snake trying to swallow a gerbil the way her gullet was contracting against my shaft.

“I can see your cock bulging in her throat,” Amy stated which only increased my arousal. She was gently squeezing her breasts as she watched Mallory and me from the corner of the room with a rapt smile on her face.

Mallory eagerly slurped up and down, thoroughly coating my cock with her saliva. I reached down and grabbed two handfuls of her hair to hold onto more than to guide her as she was doing a fantastic job. “Yeah, fucking suck that cock! You’re doing it so good. This is the best head I’ve ever had,” I stated watching her mouth continuously swallow the base of my cock while peaking up to make sure my girlfriend approved.

I looked over and could see Amy rubbing her breasts on top of her shirt, and I guessed her nipples were probably rock hard as she watched me throat fuck this slender prostitute with my hands full of her auburn hair.

With her left hand still massaging my balls and my cock assaulting her esophagus, she used her right hand to snake between my legs and found my sphincter. I could feel her bright blue nail tapping against my puckered O-ring. I had never really had a girl play with my ass before and the sensation kind of took me by surprise as little shockwaves tingled across my grundle into the base of my cock.

“Oh fuck,” I mumbled, which Mallory must have taken as encouragement because the next thing I knew, she pressed her slobbery digit into the depths of my soul which were previously unknown. She gently worked it in and out a few times before finding my prostate and began gently milking it. “Oh shit,” I moaned.

I couldn’t have stopped it even if I had wanted to, and I almost immediately started spewing my thick load down her gullet. Like the true professional she was, Mallory swallowed every drop without missing a beat. “Oh, yeah swallow it down! Such a good girl, fuck!” I exclaimed.

Mallory pulled off of my cock and inspected the lipstick ring she had left at the base. “Well, there is a little something to remember me by,” she said as she began to get to her feet. She looked over at Amy standing in the corner of the room now rubbing the front of her shorts where her gnash was no doubt dripping with nectar.

“Your boyfriend has a beautiful cock, a tight little ass, and tastes delicious too. He must have eaten a ton of pineapple just for me. I love that he was so considerate in getting ready for me,” Mallory said tauntingly. “I can’t wait to feel his tool buried in my fuck tunnel as I ride the nut out of him. Look, he’s still hard just thinking about stuffing that monster up my love chute.”

Mallory pushed me back onto the bed and then peeled off her top revealing a bright red lacy brassiere holding up her breasts. She unzipped her boots and kicked them off then slowly removed her skirt to reveal a matching red high-waisted thong. She had a nice flat stomach and her belly button was pierced with a little piece of dangly jewelry. Her black stockings turned out to be thigh highs and provided a gorgeous contrast between the red undergarments.

Reaching back to unhook her bra, she stated “I’m going to have Kyle suck on my breasts and play with my nipples. It makes my pussy get absolutely sodden.” As she removed the bra and let her breasts free, her smallish tits flopped down her chest like two fried eggs. They were not what I was expecting, but looked like breasts that had been feed a baby for an extended period of time but were no longer in use. While her tits may have been saggy, they were perhaps a B-cup but drawn down and pressed flat. She had two long, erect nipples protruding from some very large areolas, they were massive.

“You like these, Kyle? I bet you can’t wait to suck on them,” she stated pushing them back up with her hands and climbing on the bed next to me.

“Oh yeah baby, I can’t wait to play with your udders,” I replied.

I could tell she probably used to have some nice perky tits, but by the looks of them and the few stretch marks I was able to see, she must have had at least one or two kids, not that she had any baby weight remaining. Her teats had obviously been suckled by at least a few kids and possibly some clients as well. The thought instantly engorged my member and made it pulse with anticipation. I grabbed her saggy, deflated tits and began to play with them. Gently squeezing and pulling on them to watch them stretch away from her body. There was something very erotic in the way they squished in my hands as I pulled them in various directions playing with her empty milk sacks.

As I squished and mauled her chest, I began tweaking the nipples and lavishing her mammaries with kisses and small gentle bites. I moved my hands to the base of each drooping jug and squeezed forcing the blood into her already erect nipples.

“Mmmmm,” Mallory moaned in pleasure. “Work those bags baby, show mamma how much you love her dirty pillows.”

I took turns popping her nipples into my mouth, sucking on them, nibbling on the long, pointy nubs. Chewing on each breast in a biting and sucking manner.

“Shit Amy, does he play with your breasts like this? He seems to really enjoy mine and it is making me so horny. In fact, I think I’m going to have him put that mouth to work eating my soaking wet pussy! Or maybe I’ll just move straight to the main event and force that fuck pole up my tight twat and until I squirt all over the place,” Mallory mused. “I mean, look at that gorgeous cock!