Since my divorce a few years ago, I’ve continued to play the role of a submissive sissy, finally admitting that the things my Wife had once “ordered” me to do, were my own idea and sometimes even a surprise to her. She reminded me of this as she moved out, “You wear panties and shave your Ass even when you know I won’t be home, so don’t pretend I made you do any of it.” She was right and now she’s gone, living with her bull.

I had recently decided that shaving would be easier if I did it at the gym. The Shower stalls are large, feature a bench and have curtains. I wouldn’t get hair in my drain, but I had to be discrete. I generally go to the gym MFW mid to late morning and the place is generally nearly empty.

One week, because of business commitments, I missed my Friday workout. Fridays were usually my shaving day, so I was a little stubble conscious when I woke up late on Saturday morning. After breakfast, I decided I would make up my missed workout today. I packed my gym bag, including my shave gel and razors.

I was a little surprised by the crowd at the gym. I had taken a few hits of some good weed on the way, so I had a nice buzz. This may have also led to my guard being down a little and contributed to how my day went very differently than I expected.

The crowds weren’t so bad that I couldn’t get on the weight machines I like to use. I tend to prefer the machines with cables and a pin to select your weight level to lift, but most of the weight work in this gym was being done by people using Free weights and lifting bars. I enjoyed looking around at some great bodies — both male and female — between my sets.

After my workout and stretch, I got a hydro massage table for 10 minutes before heading to the locker room. The locker room was more crowded than I’d seen it before and there were lots of dudes in underwear. I grabbed my stuff for the Shower and headed to the Shower area. I usually go for the last stall to minimize traffic past my Shower, but today the only open stall was the first one. I started showering and lost myself in the warm water and leaned into the buzz. I was shaving the back of my thigh and up across my butt cheeks when I realized a part of the Shower curtain was folded open. A guy I’d noticed lifting weights earlier had been walking by and stopped suddenly. Our eyes locked for a second and he moved past. I fixed the curtain and continued shaving. I was nearly done and crouching down to get the last few hairs around the taint, and I thought I heard someone make a sound, like an approving hmmm from the other side of the curtain.

Mortified that I’d been watched, I took a long time finishing in the Shower hoping he’d be gone before I had to go back into the locker room space. I was trying to dress quickly and inconspicuously. But there he was, at the next locker with a friendly smile. He stuck his hand out and introduced himself. “Hi, I’m Shea. Want to get a cup of coffee?”

He was so friendly; I didn’t take it as a threat, and I quickly agreed. We chatted for a while about jobs and marriage at the coffee shop before he asked if I’d be willing to listen to a proposition. “No pressure. I’ll lay it out and you decide. Maybe I misread you and if so, I’ll leave. My intention is to be 100% respectful towards you.”

I was nervous, curious, and slightly aroused. The buzz had settled into a pretty good feeling overall. I encouraged him to continue.

“When I first met my Wife” he started, “she was married to a different guy. He was submissive and she cuckolded him. With me. He knew about it and participated occasionally. Eventually their relationship fell apart as she developed feelings for me and she grew less tolerant of his tendency to be passive even outside the bedroom.”

Wow. I don’t think I’ve ever heard anyone be this direct this soon after meeting them. But it felt authentic and kind in the moment.

“Have I scared you off yet?” He asked, taking a sip of coffee to allow me room to answer.

“No,” I hesitated. “You haven’t scared me off. It feels like you’ve read my browser history.”

“Awesome.” He smiled. “I don’t think I did misread you.”

“No. I was actually just like the first husband in your story, but with different characters.”

“Well, my Wife Kacy still gets turned on by the Cuckold scene. She just doesn’t want all the drama afterward. So we had a crazy idea. Here’s where the proposition comes.”

I was struggling to contain my mini erection, keeping one hand in my lap as I encouraged him to continue.

“What we are looking for is a third to join us, but not as the bull, as the cuck. It’s all role play anyway, so you’d pretend to be her husband for a night. I’d pretend to be the bull and we could have the whole scene we all crave and none of the risk inherent in starting a Cuckold relationship.”

“Wow. That’s actually brilliant. You must have a bunch of guys lining up for the chance.”

“No really,” he frowned. “We haven’t had any luck at all finding someone.”

“Are you asking me to volunteer for the job?”

“Would you like to meet Kacy?” He asked, waving her over.

She had been watching us from across the coffee shop. I’d noticed her earlier, but only briefly. She was gorgeous, long black hair, tight yoga pants hugging great curves and a smile to die for. Her eyes were mesmerizing, and I was hooked. After a little conversation we decided that tonight I would show up at their house as if I lived there, playing the dutiful husband coming home from a business trip, and Kacy and Shea would be fucking and I was to walk in on them and play the role of the tortured Cuckold.

That night I arrived at dusk. The front door was unlocked so I walked right in. I set my suitcase on the floor and walked into the kitchen and grabbed a beer. I was sipping the beer and walking absent mindedly upstairs, enjoying their nice house, removing my tie and loosening my dress shirt collar. I heard noises coming from behind the partially open door to the master suite. I crept closer. There were clothes on the floor in the hallway, leaving the trail of a flying clothes frenzy. Kacy was moaning as Shea was pounding her with an impressive cock. I stood in the doorway with my mouth agape.

I made a sound, something like a stifled sob of surprise, a mixture of sad, surprised and maybe a little turned on.

“Oh honey, I’m glad you are here. Come and stand next to me.”

I walked over and stood next to the four-poster bed that had been “our marital bed” as she casually introduced Shea. “This is Shea. He’s going to be fucking me from now on.”

“But,” I stammered, “But we are married. This is our bed”

“Oh baby” she cooed as Shea slowed his pace. “I found your Porn stash and I know this turns you on. Besides it isn’t really up to you who I fuck, is it?” She started sweet and ended firmly in control.

With that Shea resumed his earlier pace and I stood dumbfounded as they both exploded into Orgasm.

As they came down from their moment of bliss, Kacy looked up at me and told me to undo my belt and take off my pants. She chuckled as she saw my pink panties, garter, and stocking. “Look Shea, I told you he’s a sissy.”

I removed my shirt and revealed the pink bra I was wearing.

“Nice. A matching set,” He offered.

Kacy tilted her head as she looked at me and then looked down at her dripping Pussy. “Clean up time, sissy bitch.”

I knelt on the bed and lowered my face to her messy cum filled Pussy, but she gently used her foot to push my head toward Shea as she whispered, “Him first.”

I knelt and licked the combined juices that were all over his half hard cock and I gently tongued his sensitive balls. I was grateful that his balls were hair Free although he had a manly bush above his cock that tickled my nose as I enveloped his soft cock. I felt him grow as I cleaned him and once I realized he was hardening, I hesitated, but Kacy’s hand on the back of my head kept me going. He achieved a full erection after a short while, though his pubes no longer tickled my nose because I wasn’t getting enough of him down my throat to get close to them. He fucked my face a while and then Kacy told me it was time for me to clean her.

I knelt in homage to her fabulous Pussy, my Ass in the air and began cleaning her with gentle swipes of my tongue up and down her outer lips. As I began snaking my tongue inside her folds, I was aware of Shea tugging at my panties. I realized I’d made the cardinal sissy sin of putting the panties on before the garter belt. Every good sissy knows you put the panties on last so they can come off first and leave you in just stockings and the garter belt.

Shea noticed my mistake and chided me. “That’s too bad you dressed wrong because these look like nice panties. It’s a shame to ruin them.” I felt him grab each leg hole and tear my panties in half. As much as I lamented the loss of my favorite pink pair, I was more concerned that the cock that didn’t fit my mouth was about to try my Ass. I redoubled my focus on Kacy’s Pussy to distract myself as Shea spanked me a few times.

I had my tongue as far into Kacy’s Pussy as I could reach when I felt the first push of Shea’s cock into my own boi Pussy. I moaned from the pain as it entered me and Kacy’s hands stroked my head as if encouraging me to relax and accept it. I took a deep breath and he plunged in. He filled my boi Pussy, as I, with a face full of Pussy and creampie felt my cock was as hard as it has ever been.

Kacy came hard on my face and a few seconds later Shea filled me with his blast. I lay there recovering between them, breathing hard, cum dripping from both ends of mand still hard as ever. Kacy reached over and stroked my small cock gently. My cock twitched with every touch. I was dying to cum. Shea had gotten up and when he came back, he brought a cold wet washcloth that he wrapped around my cock and balls until they softened and shrank.

Kacy then slipped a chastity device on me and locked it. She held my face in her hands and kissed me sweetly. “I get to keep the key. That way we know you’ll be back. If you do a good job next time, we’ll let you cum any way and anywhere you want”

The next few weeks were agony as I didn’t hear from them. I’d been instructed not to call, that they would call me when they needed me. I respected their wishes, but this chastity device was bumming me out.

Finally, Shea called and asked if I was up for a whole day with them. One touch of my still locked cock and I agreed without pressing for details.

“Good. I’ll email you the details.” He said and hung up.

I showed up the following Saturday morning as requested in the email. I was wearing the French maid outfit they’d ordered for me and had to scamper from the driveway to the house in broad daylight (and heels, amiright gurls?) Once inside I found further instruction. I was to spend the day cleaning their house. It wasn’t a mess or anything but needed to be vacuumed, dusted, etc. I set about my chores. Several deliveries were made as I worked, and I had to answer the door in full maid attire for each one. I got curious looks from all the delivery guys and a few pats on the Ass. I was quite obviously a guy in drag and not passable.

After a few hours, Kacy arrived home and told me of further duties needed. She had me change into a different maid out fit that was less petticoat and more functioning maid. The sleeves weren’t so poufy and the skirt was slightly longer.

I spent the afternoon basically giving her a spa day at home. Manicure, pedicure, I waxed her legs and shaved her Pussy. I gave her a facial and a massage. Afterward, I helped her get dressed in a sexy high-cut sheer panty, scandalously short miniskirt, and sheer blouse with no bra.

She sent me into the spare bedroom suite and told me to Shower and put on the clothes I found on the bed. I showered, checked for stray stubble, and dried off. There were several lotions and creams that gave me a feminine smell and I used them all.

My outfit was a black lace dress that would do little to hide the white bra and panties underneath. I wore a white garter belt, remembering this time to put it and my stockings (sheer white) on before the panties.

I walked downstairs with all the confidence I could muster only to find a party going on.

Kacy grabbed me and led me to the kitchen. She handed me a serving tray and told me to circulate with the hors d’oeuvres. I can’t recall ever having so many hands grab my butt as I did that evening, circulating through the crowd and back to the kitchen for more drinks and food. I tried to get into the role, sashaying around the party and laughing off the inappropriate comments and touches. Many of the women were dressed like Kacy, so there were a lot of nipples on display.

Many of the women asked Kacy how she was able to get such obedience out of her “husband.”

She would laugh and say things like, “oh she’s a great husband,” or “once you get them in panties, the rest is easy.” Several times throughout the night, she would make me lift my skirt and show off my chastity device.

“She’s hoping for relief tonight,” she would tease. “How do we think our gurl is doing tonight? Does she deserve to cum?”

Most often the women said no. I hadn’t done enough.

Eventually, they started playing a game. It was pretty complicated, and I didn’t get it, but they all seemed to have played before and knew how it worked. There were several opportunities for bets and forfeits. The forfeits always involved removing a piece of clothing or performing a Sex act on someone else. The party was getting much more naked as the night wore on. People were kissing, fondling one another, and occasionally giving head after losing a forfeit.

One of the guests was refusing to pay of their forfeit and I realized he’d misunderstood a bet and now was being asked to give head to a man.

“No way,” he said calmly but firmly. “I won’t.”

I was circulating near him, taking drink orders so asked if there was anything I could get him. He said he’d give me $100 if I sucked off the other guest for him. I stuffed the bill in my bra and dropped to my knees. It may not have been the best blow job he ever received, but he came hard down my throat and I swallowed every drop. After that, anyone who wanted out of a forfeit could have me perform it for them for another $100 bill. I ate a ton of Pussy that night and sucked quite a few dicks. There was one woman there who seemed to like sucking a cock so much that she effectively cock blocked me on a couple of them and she didn’t even take the money. Now, that’s one girl I’d like to party with again some time.

The party began breaking up and Kacy came over and gave me a hug. “You did such a nice job tonight. You earned your reward.” She reached under my skirt and pulled my panties off. She took the key from a chain around her neck and unlocked me. Then, she led me over to the girl who had cock blocked me earlier. We embraced and she slid down taking my now hard cock in her mouth.

She looked up at me with her hand on my cock and said, “this is the smallest one tonight. I bet it’s also the fastest.”

The remaining guests giggled at my expense but I didn’t care. I just wanted to release weeks of cum. She slowly licked me before standing up and leading me to a room off the family room. It was a home gym where I had given Kacy her massage. She unzipped my dress and let it fall to the floor. She had me lie on a bench and she inverted it so my feet were above my head. She then began licking me and stroking me, teasingly asking where I wanted to cum.

I told her I wanted to cum in her Pussy.

“No, I don’t think so.” She said in a singsong fashion. “Tell me and I’ll make you cum.”

“In your mouth?” I offered more as a question than a wish.

“Hmm, you’re getting closer but I don’t think it’s my mouth. Now tell me. Where do you want your cum?” The last part was more demanding. We both knew where I wanted it, but would I say it out loud? In front of all the remaining party guests?

Finally, I was desperate, pleading to cum and I blurted out, “on my face. I want to come on my own face and in my own mouth. I want you to make me come on my own face.”

She snaked a finger into my loose Ass and stroked me faster. I had a moment of regret as I crossed the point of no return but there was no preventing the torrent of cum that splashed onto my face, some in my mouth, some dripping off my nose. As I recovered, Shea took pictures of my cum covered face and what was left of my outfit.

Kacy knelt down and whispered in my ear as she fed me strands of cum from my face and chest. “The chastity device made sure you’d be back one more time. These pics will make sure you come back every time.” She kissed my cum filled mouth and inverted the bench so I could put my dress on and drive home. I grabbed some food at a drive thru on the way home, not even caring about my attire or the dried cum on my face. I’m sure the workers had a laugh at my expense.

I fell asleep that night wondering if maybe we’ve found the perfect Cuckold relationship.