Male Chastity Servant Part 2

Continued from Male Chastity Servant Part 1

The next day, we enjoyed cuddling late into the day, enjoying coffee in bed, holding each other, touching each other’s bodies, and kissing. Karen enjoyed the sensuality and the connection as she was already quite satisfied sexually from the previous night. On the other hand, I was so horny that it felt like my cock might break the stainless steel of my chastity cage. I could tell that Karen loved this. She always told me how much she loved making me horny and frustrated and she always tried to push the boundaries of how much I could tolerate. Secretly, I loved it too. 

After a light brunch and later, a light dinner, it was time to get ready. I set out candles around the apartment, did some cleaning, and set out some nice wine while Karen prepared a cheese and charcuterie plate for her girlfriends. Around 7pm, we both showered.

In the shower, I hand washed her body. She loved when I used my hands to get to every little curve of her body. She then did the same to me, running her soapy fingers between my butt cheeks, even inserting her fingers into my asshole to thoroughly clean my anus. I loved when she did this, and it got me even hornier and more frustrated. She then used her fingers to thoroughly clean my chastity cage. I used her razor to shave any excess pubic hair around the area, and we were then ready to get rinsed off and dried.

Back in the bedroom, Karen got dressed into a sexy pair of shiny leggings and a tight turtleneck which highlighted her beautiful breasts. I selected another thong to wear for the evening, my Cover Male Malka Micro Thong, and modeled it for Karen to approve. A slap on my behind let me know she liked it. All that was left to do was wait for her girlfriends to arrive.

It got to be 8pm and by now, it was dark outside. The apartment was lit by candlelight and Karen had put on some new age music in the background when the doorbell rang.

“Go answer the door” she said, and I walked to the front door of the apartment to answer, clad only in my thong.

I opened the door and saw that Amber, Rachel, and Sarah had all arrived together. I pulled the door all the way open and let them in.

I suddenly found myself surrounded by three slightly older, but beautiful and sexy women all admiring my nearly naked body. I heard chuckles, whistles, and exclamations like “Sexy!”, “So hot!”, and “WOW!”. 

I welcomed each of them with a gentle kiss on the cheek, and they took turns touching my muscles and fondling my bare ass. I was really aroused, and I knew I would enjoy the evening immensely. I led them into the living room where Karen was and offered them each a glass of wine. As I poured wine for each of them, they took turns pulling out their smartphones to take photos of me. I was a bit self conscious, but I loved the attention. I even posed for the photos a bit.

“Who wants to go first?” asked Karen. At that, Amber stood up and walked over to me. We both stood in front of the group as Amber eyed my body. We smiled at each other and she ran her fingers over my chest. I then took her hand and led her away. We exited the living room, walked through the foyer, through the kitchen, and into Karen’s meditation room. I invited Amber to sit on the plush couch against the wall. 

Karen loved to do yoga, pilates, and mediation. Her meditation room was a soundproof room in what would have been the “servant’s quarters” when the building was constructed nearly 100 years ago. But now, it was a room where Karen could channel her inner zen. 

I stood before Amber as she relaxed on the couch and she admired my body. I had been particularly diligent with my strength training over the past few months, and I felt confident showing off my physique to her. She smiled and motioned for me to turn around, and I obliged. I turned around to let her view my thong-clad ass, and I walked around the room a bit, and then I walked over and took a seat next to her.

“Amber, what is your fantasy this evening?” I asked.

“I want you to eat my pussy until I cum” she answered. She continued “I haven’t had a man eat my pussy since my husband and I split, and I need to cum really badly. Take your time and give me a good orgasm.”

“I’d love to do that” I answered, and then got down to the business at hand.

I straddled her legs on the couch, leaning over her, holding her head gently in my hands, and showering her face with gentle kisses. Eventually, we were making out, and I could feel her tongue pressed against mine. Her hands were feeling my body, working their way around my ass, my chest, and my abs. When she worked her hands down toward my cock and felt the chastity cage locked around it, she didn’t miss a beat, only to continue to caress my balls and whatever else she could manage to touch. 

Karen had let her girlfriends know that I would be locked in a chastity cage and unable to get an erection, let alone orgasm. All three of them loved the idea of me being unable to cum so that I could only focus on their pleasure.

I was cupping Amber’s breasts and she was moaning in pleasure. I then slid down to the floor and began to kiss her thighs through her black tights, making my way closer and closer to her pussy. When I initially kissed her pussy through her tights and panties, she let out another moan. I could tell how much she was enjoying this, and it brought me immense pleasure. I looked up and saw that she had unbuttoned her shirt and removed it, along with her bra. 

I reached up and gently started pulling her tights and panties down under her miniskirt. She helped me to get them all the way off, revealing her wet pussy. I gave it a gentle kiss and she let out a tiny whimper. It smelled intoxicating, and I knew this would be an absolute pleasure.

I reached behind her to pull her hips toward me and my lips made contact with her pussy as I began to lick her clitoris. I grew aroused as she let her arousal be known through her hip gyrations and her moans. As she grew more and more aroused, I also reached up and pinched her nipples, at which she began breathing and moaning more loudly. 

Her head was tilted back and her eyes were closed. I licked with more passion and she moaned more. When I inserted my finger into her pussy, this really set her off. Her moans grew even louder and more high pitched, and from the contractions inside her pussy I could tell she was about to cum. This inspired me to tune into her with even more focus. I applied a bit of pressure to the top of the inside of her vagina with one hand, pinched a nipple with the other, and licked her clit with all the passion I could muster. Within about a minute, she was leaning back, letting out a full on scream of passion as I could feel her vaginal muscles contract tightly around my finger. I held on tight to her nipple and pressed my tongue against her clit through her climax, applying just a touch more pressure as her body commanded me to do so. As she began to recover from her orgasm, breathing heavily, I began to caress her body all over, kissing her all over, first starting with her inner thighs, the area around her pussy, and eventually back to her neck, her forehead, and her lips.

I held her in my arms for several minutes before either of us spoke a word. She was nearly in tears when she spoke. “That was amazing. I don’t think I’ve ever experienced an orgasm like that before. Thank you so much!”

We both lay down as I spooned her on the couch. I stroked her hair and kissed the back of her neck as she caught her breath. I was hornier than ever, though it gave me such deep pleasure to have brought Amber to such a deep orgasmic state that I didn’t even mind my sexual frustration. 

We lay like that for several more minutes until she got up abruptly. “I need to get back to my girlfriends. I shouldn’t monopolize you; I need to share you with the others, though I wouldn’t mind keeping you for myself. Karen is a lucky girl!”

With that, she got up and left, leaving me all alone. I tidied up enough to get the room ready for the next guest.

When I arrived back in the living room, all the girls were smiling, and Amber was just glowing so much that she stood out noticeably. I was pleased with how much she enjoyed the experience, and the thought brought me a huge amount of pleasure.

“Who is next?” I asked.

Sarah stood up. Sarah was in her mid-30’s and worked for one of the bid law firms in the city. She was on the partner track, but was still working 100 hour weeks and had no time to date or have any meaningful fun. Karen confided in me that more than anything, she craved affection. I kept this in mind as I took her hand and led her to the meditation room. I closed the door behind us and she settled in on the couch.

“You look so beautiful and sexy tonight” I told her. She blushed and smiled. I could see her admiring my body, so I walked around the room a bit and enjoyed her gaze. Then I walked over to the couch and sat next to her. We locked eyes and immediately began kissing. I could feel her hands on me, and I reached over and felt her breast, which elicited a gasp.

We collapsed together on the couch, her laying on her back, and me on my side leaning over her. I held her in my arms as I continued to kiss her on the lips, the cheek, the neck, and back to her lips. I held her close and ran my fingers through her hair as we continued kissing like horny teenagers. I let her set the pace and I took my cue from her. We continued kissing passionately for another ten minutes or so until I heard her voice. “Just lay here and hold me” she said.

I leaned over her as I lay next to her, holding her close to me. I would sometimes caress her face or feel her hair as lovers often do, but as long as I could see her enjoying the moment, I wouldn’t push her, no matter how horny I was. We were here to indulge her fantasy and pleasure. I told her how beautiful and sexy she was, and gave specifics. She seemed to love hearing about how sexy her curly hair was, how intoxicating her eyes were, and how much I loved the curve of her hips. We lay there for what seemed like quite some time until she thanked me sincerely and suggested we head back out to the living room. I could tell she was satisfied. She just needed to feel beautiful and sexy and to feel the touch of a man without any pressure to perform for him. These few minutes seemed to give her exactly what she needed, and I was grateful for the opportunity to please her. With one final kiss on the lips, I took her hand and led her out of the room and back to the living room with the girls.

Sarah took a glass of wine and quietly sat on one of the chairs in the living room, quiet and in her own world. The other girls could see that something was different as she looked as if she had just emerged from an intense massage.

It was now Rachel’s turn. I had thoroughly enjoyed the first two and was looking forward to spending time with Rachel, though I had no idea what she could want. 

Rachel was a bit more wild. She even dressed the part as part goth, part rock ‘n roller, and a hint of dominatrix all mixed together. She had sexy curves and looked breathtaking in her shiny latex pants. Just the sight of her was almost enough to make my knees buckle. 

When I went to take her by the hand and lead her to the meditation room, she pulled her hand away and smiled. 

“We’re not going anywhere. My fantasy happens right here” she said. 

She reached into her handbag and pulled out a harness and a strap-on dildo and began to attach the harness to her torso. “This will be fun. I’ve been admiring your ass in that thong all night. Karen assures me that with your chastity cage on, you can’t cum, even from being pegged. But if you feel like you might be close, you must let me know. We can’t have you cumming before we’re ready. Do you understand?” she asked. I nodded yes, and all the girls giggled.

I was led to the sofa and made to sit on it on all fours, my ass sticking out in the air facing the room. I felt a hand remove my thong, and another begin to massage my asshole with lube…a lot of lube. All of the girls were gathered around watching me, some smiling, others giggling. They seemed to be enjoying this, and although I was quite self conscious and embarrassed, I was enjoying it too. 

The hand applying the lube began to ease a finger into my asshole. I gasped aloud and all the girls chuckled. The finger moved around and I could feel my asshole loosen up, becoming more receptive to the dildo strapped to Rachel’s torso. The finger exited my anus and I felt another pressure against it.

Rachel was pressing the strap-on dildo against my anus. I reached back and spread my ass cheeks as I applied some pressure on the dildo by moving my ass back onto it. The first inch entered my asshole. Then another inch, then another, until I took the entire plastic cock inside of me.

“I love the sense of power this gives me” said Rachel as she began to slowly guide the strap-on in and out of my ass. The other girls were transfixed. They seemed absolutely fascinated by the sight of me being pegged in front of them, and Rachel was clearly loving every second.

As she began to fuck my ass, she began thrusting deeper and harder. I moaned aloud again as she slapped my ass. The girls laughed, and I only grew more turned out. I was moaning aloud to the rhythm of the thrusting, and begging Rachel to fuck me harder, and the girls were cheering her on.

Rachel was now fucking my ass hard, deep, and dominating. I could feel her power as she fucked my asshole in front of the others. I loved the complete and total submission, and I really wanted to cum.

“Please fuck me harder!” I called out to her.

“Are you gonna cum?” she asked.

“I want to cum so bad. Please…harder!” I practically yelled.

“Are you getting close to cumming” she asked again.

“Oh yes; I’m gonna cum really soon! I’m almost there!” I yelled.

With that, she immediately pulled out, leaving me to collapse on the sofa in front of everyone. All of them were laughing uncontrollably.

“I told you that you weren’t going to cum. Why in the world would you expect I’d make an exception for your little pegging episode with Rachel?” asked Karen rhetorically. All the girls laughed again.

“Now get up and fix us some drinks” she ordered. I got up and took drink orders, serving them all in nothing by my chastity cage, my thong laying on the floor.

Karen stepped out of the room for a minute and returned with a thick butt plug with a ponytail attached to it. “Lube this up and insert it” she ordered.

In front of all four of them, I knelt on the ground, covered my asshole with more lube, covered the butt plug with lube, and began to insert it into my butt. It was much larger than I had expected, and I had to insert it quite slowly, even after my ass was stretched out from the pegging. 

“Turn around so we can see your asshole” Karen ordered. I obliged.

I was now kneeling on the rug in the middle of the room, attempting to insert the largest butt plug I’ve ever inserted into my asshole. The girls loved it, and began recounting stories of ex-boyfriends trying to stick their cocks into their assholes. This was like some sort of payback for them.

I did eventually get the whole thing in my ass, though it took a minute or two to adjust. When I stood up, the ponytail tickled against my thighs. I felt ridiculous as I walked around the room with the ponytail hanging from my asshole, but the girls loved it. They ordered me to shake my ass to make it move around, and they enjoyed playing with it when I walked by. I was so turned on that my cock was pressing against the inside of my chastity cage, putting pressure on the ring. There was no hiding how turned on I was, and the girls commented on every little aspect of it. 

For the next hour or so, I continued to pour them drinks, listen to their mockery, and felt their hands all over my body and tugging at the ponytail hanging out of my asshole.

As the clock turned midnight, they collectively decided it was time to leave. I led them to the door and once again felt their hands on my body. I kissed each of them good night, and they each thanked me for the great time.

When I arrived back in the living room, Karen was sitting on the sofa with her legs spread. I knew what that meant. I knelt down and tasted her wet pussy. I had no idea she was this turned on. I never would have expected it after last night’s orgasm. The evening’s events must have gotten her turned on again.

I eagerly tasted her pussy again, and took it all in. I thoroughly enjoyed the taste and the scent, and Karen could tell. She loved that I loved her pussy. She came almost as soon as I began pinching her nipples, and I kept my tongue on her clit until her orgasm was over.

After holding her in my arms for a few minutes, she announced that she wanted to go to sleep, and got up from the sofa to head to the bedroom. I cleaned up with the ponytail still dangling from my asshole. I then went to the bathroom to take a shower, remove the ponytail butt plug, and to clean up my asshole. Once thoroughly clean, I put on a fresh thong and joined Karen in bed. She was asleep by now. I gave her a kiss on the cheek and settled in beside her. I was still incredibly horny, but my state of arousal also served as a wonderful memory of a truly fun evening. I eventually drifted off to sleep, grateful for Karen’s willingness to share me with her girlfriends.

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