Missy and Ava

This is a true story. Or mostly so.

On a small chair in my bondage room with my hands cuffed behind my back, Missy slipped a hood over my head. A classic MILF switch, Missy's primarily a pleaser and the slow, tortuous blowjob is her specialty. Tonight was no exception.

As an aside, if you want to get Missy real wet, have her start on you with her mouth. We have seen each other many times and she also likes to be tied up and pleasured, mostly with a tongue and an aggressive vibrator. And after the attachment of adjustable suction devices on her nipples, especially when in a tight hogtie on her side. She showed me a few times how do the suction things, and it's amazing just how much pressure she likes. And can take. She screams and wiggles violently against the restraints when coming, which in turn means I can't be a pussy when tying her up. When I do finally let her go, there are telltale red rope marks all over her.

Now completely blind, I could hear her shuffling around and things dropping on the floor. What a klutz. I then felt her presence in front of me and a hand wrapping above my balls and pulling hard. She giggled as I moaned at the pain and pleasure. I discovered what all the shuffling was about when I felt a thin cord being wrapped a few times around the top of my sack and then twisted. This is the kind of cord you use when you don't like somebody. It bit hard as she twisted and I wiggled to escape the pain and pleasure. But it was mostly pain and both of us know I like it. I should never have told her. Creatively, she tied off the wrap, running the cord over the edge of the wooden chair and then just below to a crossing member.

"Ow, fuck," I said. "That fucking hurts!"

Missy didn't respond, instead pulling lightly on the length of cord stretched over the chair to further increase its intensity. I jumped a little and then groaned. It was getting worse.

"Stop complaining," she ordered. Pulling a little more she then asked: "Um, should I make you feel better?"

"Yes please, dear. Will you?"

"Why should I?" she asked.

"Because I know you like to suck my cock," I replied. I knew she wanted the blow job almost as much as I did.

"Yes, but I know you want me to, so maybe I won't," she teased. I began to get hard from just talking about it.

"Oh, come on. You have to," I begged.

"No, I don't," she giggled. "OK, maybe. What exactly did you have in mind?" I could feel her hand reach around, a squeezing the base of my hardening cock. She's such a tease, I thought.

"You know, that thing you do with your tongue," I answered.

"What thing? Be specific," she ordered. I was getting harder, but my balls were really beginning to hurt.

"This is really starting to hurt," I couldn't help but say.

"I don't care, I want you to tell me," she said firmly.

"Shit, alright. When you orbit your tongue around the head." I was almost begging at this point. I didn't know what I wanted more; the orgasm or my balls unwrapped.

She pinched the head with thumb and forefinger and engulfed the length of my cock with her mouth and throat in a single motion. We were now both where we wanted to be.

"Ah, oh my God," I screamed.

I knew she now couldn't control herself. She loves a cock in her mouth. She lifted off.

"Mmm, I'm getting wet already," she advised quietly.

Going back on my cock part way down, she began what I love her to do. The tongue orbit. With an occasional deep throat, she circled my cockhead over and over with her tongue. I was getting close and I knew at the start I wouldn't last long. I hadn't seen her in well over a month and had nothing in between.

The cord pulled at my sack as I wiggled and jumped, but the nagging pain merely enhanced the mouthy pleasure. Occasionally augmenting the proceedings with her hand, Missy sucked and circled my cockhead and I soon erupted in her mouth. She then ripped my hood off and planted a hard, slimy, cum-filled kiss, pushing most of it in my mouth, which I swallowed. Still restrained, I almost had no choice, with some of it creeping down my chin. She had never done that before and I liked the surprise. She untied me and my balls, and then straddled me on the chair, with us mutually kissing and hugging each other. MILF Missy is so hot.

"Missy dear, I love your mouth," I complimented.

"And I love your cock; it's the perfect size for me. And you taste so good," she replied smiling. She was probably bullshitting me, but I took it at face value.

"Well, thank you. I never tasted my own cum before, so that was a new experience," I replied.

"I wasn't sure if you would like that, but I figured you couldn't do much about it," she laughed. "Plus, that was a lot of fucking cum, Rob."

I laughed and replied sarcastically, "Sorry, dear! It's been a while."

I continued: "I was surprised that I did like it, actually. If you asked me beforehand, I probably would have said 'no'. But I like when we push our limits."

"Maybe you should start sucking cocks," Missy observed.

"Well, I think that's going a bit too far with me. First, I'm not gay and second, I would probably suck at it."

Taking advantage of my word choice, Missy replied: "See? You're almost there! Plus, I could teach you!"

Thinking further she added: "Well, we always discuss adding a trans woman to the mix here. That might be fun. And a new experience for both of us."

Missy kind of had me on this point. We had discussed that with some frequency before and the thought of it was intriguing for the both of us. We just never acted on it. I kissed her.

"Well fuck, Missy. I don't know anyone and wouldn't know where to start," I reasoned. "Are you serious about this?"

"Yeah, come on. It would be fun. And I really want teach you how to suck a cock and watch you do it!" Missy said while grabbing my balls.

"I still have to get comfortable with this stuff and I nevertheless don't know anybody," I said.

"I do" she said.

"Well, that fucking figures. Why don't you try her out and get back to me?" I said playfully.

"Ok, well, I don't 'know' her, I know 'of' her." She added.

"Oh, well that's a big fucking difference, dear!" I blurted. But as I thought further, it kind of made sense. Missy's a sex pot. And she's been around the block more than once. She had openly disclosed during our previous meetings that she has been gang-banged, attended orgies, been tied up for photo shoots, spanked, been a dominatrix and had been foot worshipped. She looks great in heels, was my thought when I first met her, so I get the foot worship thing. And, compared to her, I'm a friggin novice.

"Ava!" Missy yelled. "Ava!"

"Ava? Who the fuck is Ava?" I asked jokingly.

"Ava is this hot little Filipino trans woman I met at one of my 'things'," Missy explained. "A while ago. She's tiny and very cute. You'd like her. Beautiful legs and a sexy accent. At the time, I knew her pretty well."

I couldn't help my interest being piqued at this point.

"You'd have to pay her, though. She a pay for play girl. An escort. Never did see her cock, however." Missy added.

"Well, that's not a show stopper. I didn't know you could go to a 'rent a trans' for this," I said.

"Now don't be disrespectful. I think we could make this work, but I have to figure out how to get hold of her." Missy said.

"Was that a double meaning, dear?" I asked sarcastically.

"If we can get her here, we will both suck her cock. She's hot!" Missy exclaimed. "And you had better do a good job!"

"Ok, well I'm not sure I want her up my ass though," I declared with a laugh.

"You will do what I tell you do to, Rob!" Missy ordered.

I think I am about to enter a new dimension, I thought to myself.

As it turned out, Ava was still escorting and, being so well connected, Missy was able to hook up with her fairly quickly. I love Missy. A series of texts followed:

"Ava would like to meet us. But there's a problem. She's on hormones and has trouble staying hard and probably can't cum. But she's a total sweetheart." Missy wrote.

I thought about how I should respond, especially with me being so unfamiliar with the whole trans world. But, "What the fuck?" I thought. "Why not?" Besides, the triple dynamic might be fun.

"Ok, if you say she's nice, let's do it. Maybe you can teach her how to suck MY cock!" I replied.

"I think it will be fun; I knew you'd go for it!" Missy responded.

"Yes, maybe you and I can tie her up in a knot!" I texted.

"Not sure she's into that, but we can ask!" Missy said. "She's in a hotel next week about an hour from you. Can you pick her up?"

"Yes, sure. The ride will be a good ice breaker," I replied. "I presume she knows we're old farts!"

"Yes, she's ok with that and she said she'll actually feel safer with us." Missy answered.

"Perfect!"

Ava, as it turned out was, in fact, a total sweetheart. Attractive, demure and delightfully engaging, I was hooked immediately. Five foot nothing with a shapely butt and beautiful legs. Take her out to dinner, and nobody would know the difference. Arriving at the hotel, I was dressed in a tie and sport coat, and I was glad I was. She was wearing a tight-fitting short one-piece dress and stylish heels. The perfect couple, ready to go out, with the possible exception of me being a bit too old for her. The quintessential gentlemen, I helped her in the car, handed her the seatbelt so she didn't have to reach, closed the door and walked around. I can't believe I'm doing this, I thought to myself as I got in. I also reasoned she had guts to meet two people she didn't really know and so I tried to keep the conversation on the way light and funny.

"I promise to bring you back in one piece, unmolested," I reassured. "Well, maybe a little molested, but the 'one-piece' thing is still good with me!"

Ava giggled. Ice getting broken. "Ha ha, I can tell you're I nice guy. We'll have fun." I adored her accent. "Yes, that's the prime directive. And Missy is a wonderful partner," I said. "We are both 'pleasers' so if you aren't having fun, neither will we."

We engaged in some small talk about how we got to where we are -- in a car, driving to my playroom -- and I continued to be amazed as to how wonderful this person next to me really was. I did, however, steer the conversation over to bondage and sex for two reasons. I wanted to know what she liked and also to find out if she was open to a bit of a different kind of fun. I was ready when she remarked that she felt bondage was all about pain and perhaps other un-fun things.

"Well, would you be open to a bit of experimentation tonight? I know you don't know me and so therefore my goal is not to scare or frighten you. And Missy will be there to save you," I added jokingly. She smiled and said "Ok, as long as there is no pain."

"Yes, no pain, only pleasure. Bondage doesn't have to be about pain. And I won't restrain you unless you ask me to. It's all up to you." Ava was my queen for the night, I would be careful to treat her as such. "Missy and I will worship you tonight. We will be there for your pleasure."

"Ohhh, that sounds like fun!" Ava quipped.

"Yes, you are my queen," I added.

I took her hand as she got out of the car and kissed it. She smiled. "We'll have a little drink and conversation before we start," I said. I hadn't seen Missy yet, but she was there when we walked in. I had told her to make herself comfortable while the two of us were on the way. As expected, Missy was already a little loose on my good bourbon and, upon Ava's entry, planted a serous kiss on her while sliding her hand up her dress. Ava didn't object, so I groped her butt while kissing her neck. I couldn't resist reaching around to her cock which, amazingly, was beginning to respond.

Grabbing a handful of Ava's hair, Missy said: "I want to see Rob sucking your cock tonight, Ava!"

"Yes, he better completely pleasure me tonight!" Ava responded in her sexy accent.

Ava's in the game! Perfect! I thought to myself.

"I would love to suck my queen's cock," I said as Missy laughed.

Ava kissed my cheek, leaned up to my ear and whispered: "And I'm going to suck yours."

Wow.

With things now getting controllably out of control, having a horny trans babe on one arm and a MILF sexpot on the other, I ushered the two to my bondage playroom which was already aglow with candles and red lighting, courtesy of my friend Missy. She's just gets it. She even brought the whiskey bottle with us. I hiked up Ava's dress as we went and slid my hand down her panties and over her perfect ass. Her panties were down to her knees when we walked through playroom door. I literally couldn't wait to remove the rest. Missy helped. Aside from the panties and shoes, the short, wrapping tie dress was all that was left, and little Ava was naked in no time, sporting a bit of a hard on. I could tell she was somewhat embarrassed.

No stranger to being naked, Missy had already dropped her skirt and blouse on the way, revealing a one-piece, open crotch fishnet body stocking. She had actually driven over to my place wearing that ensemble. With her on these stupidly tall heels, both of us towered over tiny Ava. I slid a finger in her pussy from behind as we fondled Ava, noting Missy was wet with anticipation. I worked her over with a wiggling finger fuck and her knees began to get weak and buckle. Ava noticed and responded by pinching Missy's nipples.

Missy and I did have a plan, which included administering a relaxing massage to Ava so, after pulling my clothes off, we laid her on her stomach and our four hands went to work. Ava moaned as we rubbed and fondled her, but then things began to get dirty. Missy would occasionally stroke me, stiffening me and working out some pre-cum and then directing it all to Ava's bubble butt ass crack. Sliding up and down, the feeling was exquisite and I was hard as a rock. Wasting no time, Missy got some lube and a condom, covered me up and slid me into Ava's now well-lubed asshole. It was great to have a helper while Ava, almost expecting the intruder, opened her legs as if to welcome me. I could feel her sphincter relax as I pushed and she gasped as I entered. I was careful not to be rough with her. I laid further forward on her back, supporting my weight with my arms on each side, while my cock crept further up her amazing ass. Bottoming out, I just held it there and kissed her from behind. I spied Missy fingering herself as I began to fuck Ava.

I lightly slapped the side of Ava's ass. "Squeeze me, squeeze me, dear," I ordered and Ava did just that as I slid in and out.

"Are you ok?" I asked as I did all I could to refrain from pounding her to a pulp.

"Mmm, yes, yes, you're fine. You have a nice size. Thank you for being so gentle," Ava said.

"Yes, you're my queen," I responded, kissing her. "I love my queen." I couldn't believe I was saying this but, interestingly, I meant it.

Evil Missy, however, had other ideas. While I was just about to start seriously fucking Ava's butt, she whacked mine with a leather paddle, and not very nicely.

"What was that for?" I yelled. Ava giggled.

"Get out of Ava's ass. That's not part of the plan. You're supposed to be sucking her cock and, in any case, you had better save some for me," Missy yelled. Ava giggled again.

Even Ava had turned evil at this point. "Yes," she said, "you're supposed to suck my cock tonight."

Both of them were now laughing.

I gently pulled out of Ava, but I was careful to savor the feeling of her sphincter sliding over my cockhead as I retreated. Sadly, a couple more thrusts and I would have come.

"The moment of truth, Rob!" Missy exclaimed.

"Ok, ok. Ava, you'd make a good dom I think!" I said. "Ava honey, you sit up here." I positioned her on what is essentially a sturdy, two-post chair on the wall which I had fabricated for exactly this purpose, but I was usually the one on it awaiting the blowjob. It also has provisions for restraint, in the form of leather belts that feed through a vertical post at the back.

"Ok, Ava. But I am going to bind you to the wall!", I said. "I will leave your hands free, though, OK?

Ava responded "yes" with a gorgeous smile. She was really hot.

Ava gently guided my head to her now flaccid cock and I took it in my mouth. It was a little weird for me at first, but I slowly got into it, with Missy's help.

"Circle her cock with your tongue, Rob," Missy coached. Ava was not that big -- even I was bigger -- but I kept doing as ordered. Even with her versatility issue, things began to happen. I surmised she probably couldn't come, but this was good enough. She was getting hard, but it was on again and off again. Either she was faking or my tongue and mouth work seemed to be doing a decent job since she squirmed and moaned during the process. Missy soon joined me, and Ava was now getting a double blow job, and by at least the one of us who was an expert. Thinking back to Ava's whispered offer, I was now of course planning to get on the chair myself, and I am sure Missy couldn't wait to have an armed and ready cock in her mouth. We released Ava and pulled her off the wall.

"Ok Rob, you're next!" Missy declared. She then turned to Ava: "Can you help me, Ava?"

"Oh yes! We do Rob now!" said a smiling Ava in her wonderful accent.

As I climbed aboard the padded legs, still warm from Ava's magnificent thighs and ass, I took in what was before me and what was going to happen. Here were two very hot women, one in full fishnet and heels, and the other, completely naked, olive skinned and gorgeous with a little something extra, about to mouth me to ecstasy. And Ava made good on her promise as Missy guided my cock into her mouth while pulling on my balls. Missy could tell I was getting close as both of them relentlessly licked and swirled my leaking cockhead, with Missy finally taking over for the creamy finish. I climbed off, barely able to stand up.

"Missy. Missy dear," I said. "We are just now getting to you!"

Turning to Ava, I asked: "Ava dear, what do we do with Missy?"

"I go up, you go down," Ava said laughingly.

"Perfect!" I responded. "You play with her tits while I tie her legs open."

Ava watched what I did as we both tied Missy's legs wide open with soft rope and she was soon sprawled on her back on the floor massage bedding. We left her hands free and Ava wasted no time in fondling Missy's tits and squeezing her nipples. At one point, I witnessed Ava's balls in Missy's mouth as Ava plucked and pulled. I couldn't help but think that was a dangerous place to be with me down below. Missy has a giant, easy to find clit, which probably accounts for her insatiable sex drive, and I was on it immediately with a swirling tongue. She's a "leg closer" when she comes, which I why I tied them open so I could keep up the tortuous pleasure a little longer. Nevertheless, she still managed to get her thighs mostly together while she screamed and bucked her way to a shaking orgasm. It's almost like trying to ride a bull. I left her on the floor as she came down, and pulled Ava up, mostly by her hair. I gave her a deep kiss, stuffing my tongue in her mouth as far as it would go.

"Now I'm gonna tie you up, dear," I said to Ava. "This won't hurt, I promise."

"Ok," she said sheepishly.

Taking a 25-foot length of soft cotton rope, I wound it around her, just under her "B" size tits and then back over them coming in the other way from the bight, completing the tie at her back, then over her shoulders to the front and then down and back up through the tit bra, with both ends winding up behind her. I pulled it tight, squeezing her tits. With her being so small, it was easy to see I had selected way too much rope. I stopped for a second and asked Ava if that hurt.

"No, ha, ha! That felt really nice. Very sexy," she said.

"And you look very sexy in it," I answered. "But I have all this extra rope because you're so little!"