Jim

Gerry and I had been dating for nearly a year now. I was staying over at his house during the weeknights, and he came to mine on the weekends. The sex was still quite good but was starting to get a little bland. We'd begun trying some different things, such as hitting the clubs once or twice a month, but neither of us were really into all the excessive noise or the rudeness of some of the people. We scoured the nearby sex stores, and that kept us interested for a while, but we needed more.

It was Gerry who finally said aloud what we were both considering. "I think that we need to add a third to our play every now and again. Not making it a regular thing, but something to look forward to once a month or so. What do you think?"

"Okay, but how do we decide? Male, female, or maybe another crossdresser?"

"You seem to enjoy anal as much as me, so let's consider another male that could fuck us both, or the two of you could make me airtight?" Gerry suggested with an evil little laugh and grin.

"Okay, I'm in, but where do we find someone like that?"

"Let's start with people we know that we're pretty sure would be interested. What about your pool cleaning guy? He's definitely gay!" Gerry offered.

"Oh, he's gay, alright, but also in his mid-twenties. What would a young guy like that want with a couple of old asses like ours?"

"True, true. Okay, so we need someone in our age range who we think is gay and would like to play every now and again. Hmmm?" Gerry emitted as he pondered his own statement.

"What we really need is to join a swapping group for gay men, whether they dress or not. Most of the folks that swap are at least in their late thirties or early forties, so it stands to reason that they'd also be some our age."

"Is there such a thing in this town?" Gerry asked.

"I have no idea. Let's look," I hinted as I grabbed my phone to search.

Gerry grabbed his phone as we snuggled up together and began our search. We saw more than a few for straight couples, but nothing really like what we were looking for. I did run across one that had a wider pool of LGBTQ'ers. They had a website that explained their process, so we completed the online application and waited to see what would come of it. The whole process of looking had us recharged, and we fucked like bunnies for days.

We'd mostly forgotten about signing up when I got an email a few days later. It was a 'Welcome' email, so I printed it, but held off reading it until later that evening when Gerry and I could together.

Gerry

We were just chilling on my couch as Jim fondled my breasts under my nightgown when he remembered the letter in his shirt pocket.

"I almost forgot about this. Here, you read it, Sexy," Jim said as he passed it to me.

He'd untied the lacy top, exposing my tits to his suckling mouth while I attempted to read it aloud.

"It says that there is an initiation process that basically consists of coming to their next party and meeting the other members. At the end of the meeting, there is an anonymous ballot vote to see if you seem to fit in our group. Most couples do, so don't worry." 

I paused for a moment because Jim was sucking my nips so wonderfully, but I really wanted him to pay attention to this. 

"Ahem!" I uttered loud enough to break him free before continuing.

"The next scheduled meet-up is this coming Saturday from four p.m. until whenever. It actually says whenever. Sounds like the rules are rather slack. What do you think, Honey?" I asked as his face dropped to my groin and began nibbling on my pantyhose-clad girl-cock. He really knew how to get me going. "This...This really isn't fair!" I shrieked like an overstimulated girl.

"Not fair, you say? How about this for fair!" Jim asserted and tore a hole in my hose. While I was still in shock, he sucked me deep into his mouth while plying open my waiting hole with a couple of digits. The sudden rush of adrenaline, especially after having my tits sucked so wonderfully, sent me over the edge far too quickly. I spurt repeatedly into Jim's mouth as his fingers continued to open my boy-puss.

Jim

Once Gerry quit ejaculating in my mouth, I pushed his legs back to his chest and released his cum into his opening pucker. I was going to use it as lube to pound his tight little canal into rapturous submission. With what seemed like enough to keep him slick, I pushed down my pants and underwear before plunging wholeheartedly into him. It had been a while since I'd taken him so aggressively, even though I knew that he loved it. We'd fallen into that love trap, where you care so deeply that you're afraid to treat each other like the sluts that you truly are, but not tonight. I was going to fuck him the way that we both craved.

With that first hard and deep penetration, Gerry knew where it was gonna go.

"That's it! Fuck me good and hard! Remind me that this ass is yours!" Gerry wailed as I commenced using him like a two-dollar whore.

My eyes were closed as I remembered that first time when I fucked him hard on top of his table saw. I wasn't one hundred percent sure that it was him, but secretly hoped that it was. I was pumping that firm, plump ass for all I was worth as he ejaculated onto the sawdust-covered floor. I wasn't far behind as I ejected my seed deep into his bowels.

Stirred back into reality by Gerry's orgasmic wail, I found myself fucking him for all I was worth as his spunk spayed across his own belly and chest. I was very close to cumming myself as I continued to plow between his spread thighs.

"God, yesss! Give me your seed, you sexy bastard! I'm yours to impregnate with your loving spunk," Gerry trailed off as I felt the stirrings in my loins and his colon clench through our shared orgasms. In the sunset of our sexual fun, we snuggled close as my hard-on slowly diminished.  

"I can't wait to share you with another and see the look on your face as they pound that firm little ass into oblivion as I just did. Then to fill your throat with my jizz as they fill your ass with theirs. We're going to have so much fun giving you everything that your little slut heart desires," I offered while kissing his neck and ears.

Gerry

Lying there with Jim's receding cock still half inside my leaking puss as he continued to kiss on me, I reveled in the feeling of being his woman. I'd gotten everything I ever dreamed of when I began dressing all those years ago, but still, I wanted more. What was wrong with what we had together? We'd already admitted our love for each other. Why wasn't it enough for me?

That's when Jim said what he did about sharing me with another. It seemed that he got off on it as much as I did, so why not? Besides, if it didn't work out, we could just try something or someone else. Either way, we had each other, and that's what really mattered.

Saturday came, and I was a mess. I spent all morning trying to find some alluring but not too slutty. Jim was of little help as I showed off for him. All he wanted to do was feel me up like a horny teenage boy that I had to fight off numerous times. I guess that I should have been flattered by all the attention, but honestly, what is with guys sometimes?

It all struck me so suddenly. Here I was, complaining about a man who wanted me so badly that he couldn't keep his hands off my body. This was all I'd dreamed about for so many years. A man that would accept me as his woman and want me as such. Disappearing back into my walk-in closet, I opted for something so sheer and tiny that he wouldn't be able to stop himself. I added a garter belt and my sheerest stockings, leaving myself ready for a long bit of wanton sex.

Jim

I knew that Gerry wanted my opinion on what to wear, but all the talk about looking good to be shared had me hard as steel. I really was trying to be good and helpful, but each time Gerry showed me another dress or skirt, I just wanted to take them off of him and have my way with that perfectly plump ass. This last time, he again vanished into his closet for another costume change. Only this time seemed much longer than the last.

I called out from the kitchen while making us lunch, "Hey, Honey. Have you decided on something, or are you getting tired of me groping your splendid body?"

"No, I've got one more that I'd like you to check out," Gerry whispered sexily as he rounded the corner in basically a sheer negligee.

"Oh, fuck!" I yelped.

"Yeah, that's what I was hoping for, "Gerry responded before lying spread-eagle on the couch.

I dropped the lunchmeat and simply stared. There Gerry lie like an insatiable trollop, plying his boy-puss and tickling his clitty. The soft coos emanating from his plump red lips were like a snake charmer's pungi calling to the serpent in my pants. Although it had been at half-mast most of the day due to the sexy clothing that he paraded around in front of me, it rapidly rose to full tumescence within moments.

I moved quickly to the couch, unbuttoning my pants along the way. They wiggled their way down my legs as I shuffled over frantically. Nearly there, I kicked my pants away while aiming my stiffy at his opening pucker. However, it seemed that Gerry had other plans as I neared his open backdoor.

Gerry

I had teased Jim all day while showing off the multitude of outfits that I was considering for the evening's events. Finally, deciding on something simple and nearly see-through, I fell onto my back on the sofa and spread my legs like a common whore. I stroked just the tip of my shrunken clitty and drilled my eager cum pocket as it awaited Jim's prick. Finally, after what seemed like minutes but was only seconds, he began dropping his drawers and shuffling my way. When he was almost to me, I slid down and off the couch to suck his bobbing hard-on into my mouth.

I guess it was a combination of a couple of things that caused my reaction, but mainly because I really wanted to taste his cum. The fact that I didn't want to have to take another shower may have played a part, also. I can be a bit of a Princess sometimes. All that aside, I always love getting on my knees for a hard cock full of spunk, and that especially applied to the only one I've been sucking for the last year.

Jim seemed a bit surprised by my move but didn't hesitate to take ahold of the back of my head as I pumped his excited prick. I knew that he loved me, but even with him, I sometimes felt a little cheap as I knelt down to suck him off. But, to be honest, the need to be his cumdump turned me on much more than I cared to say. I guess that's how we ended up where we were that afternoon as we prepped to go and pick out a stranger or two to share me with. As Jim neared his peak, I was imagining being spit-roast with a stranger in my ass when it was actually two of my fingers plying my hole.  

Jim

As I pumped my seed into Gerry's gullet, I felt the need to taste his cum as well. With the last bit dribbled across his caressing tongue, I pulled him up and pushed him back on the sofa. Pressing his legs apart, I sucked his girly appendage into my mouth for some good old hard sucking. Gerry loved a fevered oral draft as much as anyone. I also knew that he only blew me to keep from having to take another shower. With oral, it was a quick and easy cleanup and left us both temporarily sated.

I really tried to stay focused on his growing clit, but his smooth and inviting pucker was irresistible. Lapping across his frenulum and slowly downward, I sucked his jewels into my mouth and rolled them around to his moaning delight. Continuing my trek further south, I began to rim and tickle his anus lightly. Gerry's ankles found the back of my head and pressed me in much closer.  

As my tongue naturally dug heartily into his crevice, I heard, "Oh, you amazingly dirty bastard! Please marry me and do this every day," he huffed with his orgasm approaching rapidly. Knowing that he was nearly there, I traced my tongue upward across his rolling sack, just in time to take the first of his jettisons into my hungry mouth. I sucked and swallowed until he was empty and soft before finding his pucker for another minute or so. I loved licking his sensitive girly puss after he'd cum just to keep him squirming a little longer.

Gerry

It was moments like this as Jim lapped at my little star after that wonderful blowjob that made me wonder why I was even considering our upcoming adventure this afternoon. This man was nothing short of wonderful in every way, and here I was, desiring another for our sexual play. If it weren't for the fact that he was as wanting of this as I was, I would never even consider bringing another into our sex life. It wasn't for a lack of caring but more for keeping things fun sexually. We were at that age that we could let go of jealousies and just enjoy the sexual contact that was shared with another.

As Jim released my splayed thighs and gave me a quick peck on the lips, I yearned to feel his cock deep inside me. But instead, he pulled me to my feet, swatted my ass, and led me to the bathroom, where we both cleaned up and redressed for the party. I obviously took a little longer, having to reapply my makeup, but stayed panty-free per Jim's appeal. By the time I was finished getting dolled up and redressed, we hopped in the car and were on our way.

"Are you nervous?" Jim inquired as his free hand stroked my stocking-clad thigh while he drove.

"Yes, a little. But mostly about whether this will cause us a problem," I replied honestly.

"All of that has been running through my head for months now. And although I have felt minor pangs of jealousy, the thought of sharing you and giving even more pleasure while getting some of my own has been overpowering," Jim offered as he caressed my bare inner thigh above my stockings.

To be continued...