HOLIDAY, TIME TO PLAY

Author’s note:

What started as a short story ended up rather long and probably needs a part two, hopefully I can get around to it. I appreciate constructive feedback or ideas where you think the story should go.

We love getting away interstate, where nobody knows us. No kids to worry about, just some significant downtime, a little fishing, a little drinking but most importantly, a chance to let our kinkier side play.

We have been married for twenty-five years, a couple of kids, both still at home. We enjoy a good sex life in the norm, but in the past few years, we have been opening our horizons and exploring new options in the bedroom, and being away helps us expand it a little more.

I suppose Sue has always been the controller in our relationship. Over the past few years, she has become more dominant, which suites my submissive nature. I confessed to her a few years ago, my desire to be more submissive to her needs even if that meant she needed to be firmer with me.

When I had been researching the net on ways to spice up our love life, in no way was our love life terrible, but it was becoming a little mundane. I had come across a few sites about FLR, Female Led Relationships. Many of the articles seemed a bit extreme; however, the basic principle of the woman in charge appealed to me; I broached the subject with Sue, showed her a few of the sites I had been viewing. In the beginning, she was very reluctant, although she agreed to do her research on it with an open mind.

Some of the benefits appealed to her, some didn’t, pointing out some obvious flaws in the articles which I agreed with. I didn’t want her to sleep with others, I didn’t want to give her full control of the finances, and I didn’t want to become her sissy husband. My how things have changed since then! But that is a story that can be told later.

Fast forward five years. I was standing in the bathroom of the motel room that Sue had booked and paid for, applying red lipstick to my lips before donning and brushing out the shoulder-length wig to complete my outfit for the evening. I wore a simple floral sleeveless dress that finished just above the knees, underneath a matching G-string and bra set along with breast forms that accentuated my cleavage and finished with a pair of strap shoes with a little two-inch heel.

We had been out for dinner and had returned to the motel to sit outside, enjoy the fresh air, have a few drinks, and watch the sunset over the lake. We had discussed the possibility of me going out to dinner dressed as Roxy, my female persona, but I still wasn’t comfortable being seen in public. Sue wasn’t ecstatic about my reluctance, as she liked to push my boundaries, and we had discussed before the trip her desire for me to go out in public as a challenge, one that I would be well rewarded.

One final look in the mirror, and I was ready to join Sue outside. As I walked towards the courtyard, I could hear voices. Sue was talking to someone, and from the sounds of it, Grant and Ann, the couple from next door. They were about the same age as us, and we had met them earlier, shortly after they had arrived. They seemed nice enough, and Sue had promised them a catch-up, seams they took up her offer.

I quickly grabbed my phone and texted Sue: “Are they going to be here long. Make an excuse, and I’ll quickly get changed.”

Five seconds later, her reply: “don’t bother changing. Come out here, Roxy.”

Before I could reply, my phone pinged again: “NOW…. you sissy slut”

My stomach knotted. I sensed from her text’s tone that I didn’t have a choice, so with a deep breath, I nervously walked out.

As I stepped over the threshold, both Ann and Grants’ jaws dropped as they stared in disbelief. If I weren’t so scared, I would have laughed.

Sue broke the awkward silence by saying, “guys, you met Rob earlier.” ” Now I’d like you to meet Roxy” “Roxy, this is Ann and Grant, say hello.”

I turned to Ann and gave a little curtsey, “Hi Ann,” she offered her hand out, and I gently shook it as she gave a little giggle. Grant had started to stand as I turned towards him, a stunned look on his face as he offered his hand, I reached for it “Hi Grant, I’m Roxy” he replied, “Hi Roxy, nice to meet you” and still in a daze, instinctively leaned in and kissed my cheek, before jumping back shocked at what he had just done “Shit, I’m sorry” he stammered.

Now it was my turned to be stunned for a second. Both girls burst out laughing at the situation, and Ann said, “Better watch out, Roxy, looks like you have an admirer” The girls laughed again as both Grant and myself turned bright red, Grant from the faux par he had just executed and on my part because I enjoyed the compliment. Ann told Grant to sit, which he did, and proceeded to finish off his drink. Grant looked at Ann, and they smiled at each other, and she said, “You can be such an idiot sometimes, Grant, but I still love you” they both laughed when Grant replied, “But I was just trying to be polite.”

Sue and I joined in on the laughter. Before I sat down, Sue asked me to get a fresh round of drinks for everyone. Grant picked up a six-pack of Bourbon and Coke, placed them on the table, and said that he and Ann were ok. “Nonsense,” said Sue. “Roxy, please put these in the fridge and bring out some glasses and ice” “I’ll have another wine, and your drinks are also in the fridge.”

Dutifully I gathered the cans, found some glasses and a serving tray, put some ice into the bucket, cans into the fridge and grabbed Sue’s Bottle of red and my Vodka cruiser, and walked back out, placing the tray on the table. I proceeded to make a fresh round for all, handing them out, finally sitting down opposite Grant, making sure to flatten my dress before I sat, back straight with my legs folded underneath me, trying to catch up with the conversation I had missed.

Sue explained to Ann and Grant how our relationship’s dynamics worked, how it started as an extension to our relationship, to spice things up, but finished up being a significant part of our lives. What had started as a bit of fun now and then had evolved into a power struggle.

Over time Sue had come to embrace the power exchange and was increasingly unwilling to share it or, worse, give it back. She liked it when she came home from work, and I had done the housework or the meals prepared, a glass of wine waiting for her and afterward a relaxing massage, only to be disappointed when the role play ended, and things went back to normal. She felt defeated at these moments and decided to do some more research.

Both Grant and Ann were fascinated with Sue’s story, asking questions, or looking at me for confirmation. I also noticed that Grant seemed, at times, distracted. I could feel him staring at me, his gaze lingering on my shaved, smooth legs or trying to get a sneaky look at my cleavage. I was surprised at myself for being so relaxed. Nobody, other than Sue, had seen me dressed. Comfortable with my surroundings, I allowed my mind to wander into “What if” territory. I decided that if the opportunity arose, I would flirt with Grant.

I had never considered being with a man until recently. Sue had introduced a strap on to our lovemaking a little while back. Pretending to be her lover’s cock and that I should suck it before he fucks her with it. She would then make me wear it and fuck her while she explained to me how much bigger he was, how good it felt, how I would never know what it’s like to be fucked.

After she orgasmed, I would either be denied release or told to stand facing the corner and pull myself to climax as she didn’t want to see my pathetic cock. She would even do a count down, and if I didn’t cum within the allotted time, I would be denied the orgasm. Subsequently, I would hunch in the corner, humiliating myself by feverously jerking away until I spurted my seed into my hand with Sue laughing in the background. For some reason, I loved it.

It wasn’t long after that Sue said to me, while I was trying to deep throat her plastic cock, that it looked like I was enjoying it and that maybe it was time to fuck me with it. “would you like that?” “would you like me to fuck that slutty arse of yours and truly make you my property?” I replied by forcing myself down on her plastic phallus and gagging. Since that night, I have been subjected to regular pegging and crave that plastic cock in my arse.

I was snapped back to the present conversation when I heard Sue say. “But the real turning point came when I realized that, while we pretended to exchange power, it was only when Rob wanted it to be that way did it happen.” That’s when I came across an article titled “Whoever has the pussy, has the power” “That article changed my life, and I have adopted that mantra ever since.”

There was a pause in the conversation as both Ann and Grant sat back and let that sink in. I took the opportunity to refill the glasses with fresh drinks quickly. I was even able to throw some crackers and dip together and brought them out for all to share.

I was doing my best impression of a Stepford wife, handing out the drinks and returning with the plater of dips serving each one at a time. I made a point of standing straight and bending from the hips when I served the ladies, and I could feel Grant’s eyes burning into my backside as he tried to see what I was wearing underneath and the same when I served Grant, I made sure he could get a good view down the front of my dress.

Ann quipped, “Well, it sounds like it’s been a journey, but you seem to have Roxy well trained now,” both women laughed. “So tell me, Sue” “How did the cross-dressing start?” “Was she always into it?”

When I sat back down, I deliberately let my dress ride up, with my legs slightly apart. Grant had a full view of my panty covered cock for a few seconds before I adjusted myself. I giggled to myself as his eyes bugged out, and he nearly choked on his cracker. He looked at me and smiled with a slight approving nod of his head.

“No, he wasn’t, Ann,” Sue replied, “In fact, he was adamant that he never would wear panties!”

Sue explained how, once she realised that she didn’t have the control or the power over me, she thought she had. She set out to rectify it permanently. Sue started initiating the roleplay games more frequently, each time pushing the boundaries further, repeatedly denying my orgasms with petty excuses, eventually introducing a chastity cage to the fun. I was reluctant to play along, but with her constant teasing and denial, my cock started thinking for me, and I relented.

She played it perfectly. At first, I would only wear it short term, maybe overnight, then the whole weekend. She had the key, but a spare was available in case of emergency in our safe. Then, at the end of one weekend, she suggested a week next time before she unlocked me. I was that desperate to be released, I agreed. Besides, I was getting used to wearing it by then, and I always had the spare if it got too much.

Halfway through the first week, I was horny as fuck; I grabbed the emergency key while she was out shopping, released myself and jerked off to a massive orgasm, locked myself up, and put the key back, all before she got home. Sue walked in from shopping and knew precisely what had happened, and she could tell by my attitude and my demure that I had empty balls. She stood over me, rage boiling in her eyes, staring me down as I tried to stammer out a lie that I didn’t do it. Eventually, I confessed, told her I was sorry but added that a man has needs; besides, I wear the pants in this house.

Sue stormed off into the bedroom, calmly saying over her shoulder, that’s it, game over, and I had better put the shopping away before she got back.

I finished off the show I was watching and wandered out into the kitchen; just as I was putting the last of the shopping away, Sue walked in completely naked, the key to my cage on a chain around her neck. As she walked towards me, she spoke calmly and seductively, with a hint of authority in her voice. “Listen here, buster, a man might have needs but so does a woman” “I haven’t had pleasure either since you’ve been locked up” “Strip for me, NOW!”

I was in shock. I thought I’d at least get the cold shoulder for a day or two; instead, I was getting this stupid cage off and going balls deep into my sexy wife. I was naked in a flash, standing there, my cock already starting to harden in anticipation, despite the confinement of the cage. Sue walked to me, put her arms around my neck, and kissed me passionately.

We broke from the kiss, her arms still around my shoulders. I told her I was sorry. She told me that she was as well, but it’s for your own good. I looked at her puzzled as her expression changed. She gripped the back of my neck and smashed her knee into my exposed balls.

My balls’ pain squashed between her knee, and the ring of the steel cage was excruciating. I dropped to the floor with a thud, my hands cupped my ball sack, and my knees came up into the fetal position, my mouth wide open, but I could only manage a guttural sound.

Sue stood over me, one foot on either side of my head; she squatted down, grabbed a handful of my hair, and made me look at her. She told me she loved me, but it was my idea to start this game, but she was sick of playing it by my rules. The initial shock from the blow to my balls had subsided slightly, but I was having trouble concentrating. She shook my head to get my attention.

See this pussy, she squatted and lifted my head a little. I could see nothing but her shaved pussy, slightly agape from squatting over my face, her lips and entrance glistened with her juices, her clit hard and popping out from under its hood. “See this pussy” she repeated. “If you ever want to get your cock back in there, you will play this game the way I want it, not your way” “you will do as I say, when I say it” “We will see who wears the pants in this house” “Starting now.”

With that, she put my head to the floor and squatted directly over my mouth, “Eat my pussy, bitch.” It took less than 10 seconds of me licking before she erupted in one of the more powerful orgasms I had witnessed from her; her body shook from head to toes, flooding my mouth with juices. I struggled to swallow and breathe at the same time, and it was like I was drowning.

Eventually, she fell to the side spent and laid there for a few seconds before getting up and announcing that things would change around here, and I had better get used to it. She walked away, telling me she was having a shower and to make sure this mess was cleaned up before the kids got home.

I sat up on the floor, one hand still cupping and supporting my crushed balls; the pain was now down to a numbness along with the pain associated with trying to get an erection inside the cage. I couldn’t believe that I was so aroused after receiving such a traumatic blow, my face covered in Sue’s juices; even the floor showed evidence of her massive orgasm.

Sue hadn’t gone into quite as much detail when she related the story to Ann and Grant, and although Grant had cringed when Sue explained how she felt the balls squash up and flatten against the ring of the cage, he sat intently listing to her continue.

Sue explained how the empowerment she felt at that moment was exhilarating, and when she commanded me to lick her. I did so without complaint, and she said it was like a switch had been flicked on as waves of pleasure shot through her body released through that powerful orgasm. She knew then what she wanted; she suspected, by my compliance, that it was what I also wanted, A permanent female Led relationship, complete ownership of her submissive husband.

By the time Sue exited the bathroom, I had cleaned up and hobbled to the bedroom and was sitting on the bed, still cradling my swollen balls. Still naked from her shower, her goddess body seemed more alluring than ever. She looked down on me, hands on her hips, and simply said, “Well!”

I told her it was fucking awesome, my balls were sore as hell, but I loved it. Sue smiled and said, “Good, there is going to be some drastic changes around here, and you had better conform, or you can leave.” “I’m not going back; this is the new me from now on.”

I asked about taking the cage off to ease some pressure on my balls, and she replied, “NO” “You cheated; you need to earn the right to have it removed.” “I’ll show you who wears the pants in this house.”

Grant let out a “Fuck me” as he sat back in his chair. Ann let out a little moan as she clasped her thighs together and shook, just a little bit. Composing herself a little, she simply said, “that’s so hot!”

“So anyway, Ann, to answer your question regarding the crossdressing,” Sue continued, “For Rob, to get the cage off, had to admit that I wore the pants in our house.” Grant pipped in with, “that’s a simple enough request” Sue smiled “yes, Grant it is” “But the conclusion to that was” “If he didn’t wear the pants, then he didn’t deserve the right to wear men’s underwear.”

“It took two weeks of wearing the cage, with his purple bruised balls, before he relented.” “We went shopping that day, for a variety of women’s panties, came home and had a commitment ceremony of sorts where he burnt all his men’s underwear” “He hasn’t worn anything but since!” “From there, it didn’t take too long for Rob to embrace his feminine side and accept Roxy as his alter ego.” “It’s still evolving, hard with the kids at home, and they have no idea that daddy is a submissive sissy hubby, which is why we take regular trips away.”

Both Ann and Grant looked at me and laughed. Ann turned to Grant and said, “I wouldn’t laugh too loud, GRETTA, I think there may be a few changes in our house as well” “This sounds like fun” Ann had emphasized the word fun as she turned back to Sue and gave her a wink. The three of us laughed as Grant sat in stunned silence for the second time that night.

It was starting to get late, and although we were still chatting, it was time to finish up. We decided, well, the girls did, to catch up the next day, and we said our goodbyes. Ann came to me, gave me a hug and a peck on the cheek and turning to Sue, did the same, but added that she was so glad to have met us both and was looking forward to chatting again. She leaned in and kissed her cheek once more and whispered, I might need some more tips, and laughed.

Grant lent over to Sue and kissed her on the cheek as well and said, “Thank you for a fantastic night.” He awkwardly raised his hand to shake mine when Ann pipped in with, “Don’t be shy now, give Roxy a proper goodbye.

” We all giggled a bit, and Grant wrapped his arms around me, lifting me off the floor, swung me around, put me back down, and kissed my cheek; he held the embrace for a second or two longer than necessary and with my groin pressed into his I could feel his hard cock pressing into me. I smiled, leaned in, kissed his cheek, and stepped back and told them both that it was our pleasure to host, and thanked them for not being judgemental.

After they left, Sue came up behind me, wrapped her arms around me, gave me a big hug, and kissed my neck. “I am so proud of you,” she whispered in my ear, “finish cleaning up and come to bed; I think you deserve a treat.”

I cleaned up as quickly as I could; by the time I got back inside, Sue was already in bed, my pink lace nighty was laid across the end of the bed. I grabbed the nighty and went to the bathroom to change; however, Sue said for me to leave the makeup and wig on then come back.

The see-through nighty left nothing to the imagination, hanging down to mid-thigh. It modestly covered my shaved cock and balls, I had removed the bra and breast forms, and my nipples hardened under the lacy material, a quick touch up of my makeup and a brush of the wig, and I returned to the bedroom.
Sue had removed the covers and was now lying naked on the bed, her naked form, beautiful in the dim light. My gaze was quickly drawn down from her face, past her heaving breasts to the rubber strap on that she wore, all 7″ of it hard and inviting.

I lay down beside her as she embraced me and drew me in for a kiss, deep and passionate. Instinctively my hand cupped her breast, my thumb brushing over her nipple, her back arched as she moaned into the kiss before breaking it.

“Fuck I’m horny,” she huskily whispered, “The whole night has been exhilarating” “How do you feel?”

I told her I felt liberated; the adrenalin rush had made my whole body tingle. At first, I was reluctant to expose Roxy like that, but that I was glad she had forced me to push my boundaries and that tonight had been, I hoped, a new chapter in our lives.

Sue agreed and told me how wet she had got, talking to them, trying to shock them, and when Grant had lifted me and kissed my cheek that she had nearly orgasmed. She commented on how she loved watching Roxy flirt with Grant and felt Ann had taken to our story. We both laughed when I said, “Poor Grant, he has no idea what he is in for.”

We kissed again before I moved my mouth to cover her nipple and started to suck gently on the firm bud; my hand wandered down to her plastic cock. The strap-on, while 7″ long, was circumcised; it also had a reverse nub of about 4″ inserted into Sue’s vagina and was held snuggly into place by leather straps. As I gripped it, Sue moaned, “Roxy, imagine that this is Grants’ cock, you have in your hand” “Show me how Roxy would pleasure Grant.”

I moaned as she said that my hand gripped it. I pushed it forward, between her legs, and started with long slow strokes; at the end of each stroke, my thumb would brush over the knob of the cock. Sue, the nub inside her, could feel each stroke would pump her in rhythm, and the base would stimulate her clit. I increased my pace slightly while still sucking on Sue’s nipple, and she started to writhe about moaning; her hips began to roll, thrusting to meet my strokes.

Her orgasm hit her in a rush, legs clamping together as she rolled to the side, her chest heaved and fell as she moaned out long and loud, before falling back on the bed. I stopped and looked at her, glowing in her orgasmic bliss. She smiled at me. “That’s one,” she said. With that, she pushed my head down between her legs. “I’m sure Roxy can do better; why don’t you show Grant how good a sissy cocksucker you are.”

I didn’t need any encouragement, and I quickly set about doing just that. I scooted down the bed a bit and positioned my mouth over the plastic cock, imagining that it was real and attached to Grant. My left hand at the base, my tongue darted out and licked the head and shaft, coating it in saliva, before opening my mouth and engulfing the mushroom knob; my tongue danced around the head as I sucked it deeper into my mouth.

My right hand grabbed my rock-hard cock, and I started to jerk myself, imagining I was sucking a real cock for the first time, Grants cock. Sue brushed my hair away from my face so that she could see before grabbing my head, pushing it further down on her plastic cock. “Don’t you cum yet, you sissy slut” “Grant wants to fuck Roxy’s sissy arse before you are allowed to cum” Sue pushed harder, forcing me to gag on Grant’s cock. I edged myself to the point of nearly cumming, before stopping, my cock rock hard and primed to explode.

Sue released the pressure on my head, allowing me to stop sucking for a second, the plastic cock coated in my saliva. Still, with her hand on my head, Sue grabbed the cock and slapped the side of my face with it. “Does Roxy want to be fucked by Grant’s cock” I stared at the cock before me and simply nodded yes. “Tell me,” Sue demanded as she slapped the side of my face again with her fake cock.

I looked up at her. “Yes, please fuck my slutty sissy arse with Grant’s cock”

Sue smiled and pushed me off her, telling me to get on my back, legs up slut. Sue stood and grabbed the lube coating her cock before reaching between my butt cheeks and applying more. Her fingers were rough as they probed my hole; she seemed in a hurry. She had me scoot over to the side of the bed, so my butt was dangling on the edge. She lifted my legs to her shoulders and positioned the strap-on between my cheeks. “spread them,” she commanded, and as I parted my butt cheeks, I felt the tip of her cock rest at the entrance of my rosebud.

Sue looked down at me from her elevated position, smiled an evil grin, and said, “Is Roxy ready to take Grant’s cock for the first time?” I moaned and replied, “Yes, Please.” With that, Sue pushed the knob of her cock into the opening of my slutty arse. The involuntary pain hit as the head of the cock passed into me; I grimaced; Sue stopped to let me adjust before withdrawing slightly and pushing in again. The cock slid in a few inches, stretching me, again I moaned, about halfway in, Sue found resistance again. she backed off a little and held still.

My breathing took over, and with each outward breath, I rocked my pelvis until I managed to move the blockage to the side and was rewarded with the rest of the plastic cock sliding effortlessly into me until I felt Sues crotch resting against my butt cheeks. I let out a long low moan as Sue just stopped balls deep inside me, allowing me to accommodate this intruder.

“I think Roxy likes Grant’s cock in her sissy hole,” Sue said as she smiled down on me. “Fuck yeah,” I replied. I started to hump back on the plastic cock, and I looked at Sue; I grinned and said, “Fuck me, Grant, fuck my sissy slut hole, make me your bitch”

That was all it took; Sue started pounding my arse with her pretend cock, long strokes, increasing her speed. Telling me how Grant was going to destroy my fuck hole, how he was going to spill his seed deep inside me. How much of a sissy slut I was, how I deserved to fucked hard and fast.

I grabbed my cock and started pumping, fuck I was close to cumming. Sue slapped my hand away. “not yet slut” “I will tell you when.” She replaced my hand with hers and started teasing my shaft as she increased the pace once more, pounding away at me. She could feel each stroke reciprocated through her end of the strap on, building her orgasm. She slowed down her pumping slightly but increased the speed of her jerking my cock; I couldn’t take it any longer; my back arched as Sue gave one final pound into me.

My cum started to spurt from my cock seconds before Sue’s orgasm rocked her body; she let go of my cock and grabbed my legs for support as her knees gave out as her body shook. Another spurt of my cum exploded from me, and I quickly grabbed my cock and continued to jerk, each spasm causing my rectal muscles to grip around the strap on until we were both done. Sue withdrew the strap on from my well fucked hole before collapsing on top of me.

We rested like that for a few minutes before looking at each other and laughing our heads off. We both agreed it was a fitting end to the night and at the same time wondered what tomorrow would bring.

Also read: Sissy Wedding Stories