Serving as My Wife's Sissy Pt. 05

Story Info
First Evening at the BDSM Resort.
3.2k words
4.44
9.3k
8

Part 5 of the 5 part series

Updated 07/12/2023
Created 04/28/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Cindy finished going over the basic rules of the resort and got us checked in, including taking our health certificates. While she had been doing this Julie had pulled a couple of things out of her purse.

"Thank you," replied Julia and then she turned to me and said, "Loose the panties."

I took off the panties and put them with the rest of my clothes. Julie took her nail clippers and clipped the cable tie that was linking the two rings on by penis and scrotum. She then picked up the padlock and a small bell on a four-inch chain. She locked the rings back together while attaching the bell to the padlock with the chain. Now with every step I took the bell would ring. I noticed Cindy smiling at me as she watched Julie locking my clitty to my balls.

Cindy said, "Let me get one of our hostesses to show you to your cabin. Jena get in here."

With that this person appeared from around a corner. She was female in presentation, but the large clitty/cock said she was definitely male. She was wearing high-heeled sandals and pink stocking. Her blonde hair was shoulder length and her c-cup breasts were caped with large pierced nipples. Her make-up was definitely feminine, if a little excessive.

She looked and Cindy and said, "Yes, Madame, how can I help?"

"Jena, will you show Mistress Julie and sissy Nora to cabin 15. Julie it is after 5:30 you may want to get unpacked and ready for dinner, your dining room reservation is 7:00 this evening. One other thing Jena please take them by the clinic so we can get the samples for our health test. Julie we always run our own tests for STD and will have the results in the morning here at the front desk. Please refrain from extra couple sex until we get the results."

Julie responded, "Thank you Cindy."

With that Jena started by leading, us out the right-side door and along a path. As we walked along Jena pointed out things such as the dining room, pool, dungeon, path to the beach, etc. After stopping at the clinic, we walked a short distance and started to walk by the cabins which were separated from one another to give each one some privacy.

A couple was coming down the path from the opposite direction. The lady, who appeared to be in her fifties, but was very sexy was wearing sandals and black bikini bottom. In her left hand she had a leash that was attached to a collar on the man who was on his hand and knees following along behind her. He had a head cover on that gave him dog ears and a butt plug in his anus with dog tail hanging out behind him. As we got close, she stopped and the man got off the path by a tree and lifted his leg and pissed. Julie said hello to the lady as we passed and asked, "May I pet your dog?"

"You most certainly may. His name is Butch."

Julie reached down and petted Butch saying, "Thank you. Would you like to join us for dinner this evening?"

The lady replied, "We would love to join you. My name is Barb. What time is your reservation?"

"Thank you, Barb, I am Julie and this is sissy Nora. Our reservation is for 7:00 and we will see you then."

"Great, we will see you then."

With that Jena lead us the rest of the way to our cabin and showed us the important things around the cabin. After she left Julie said, "Let's unpack and get cleaned up for dinner."

"That will work, why don't you ger a shower as it will take you longer and I will start unpacking," I suggested.

Julie undressed and headed for the shower while I unpacked our suit cases putting things away. When Julie came out of the shower she said, "That felt good. You need to go jump in and make sure you shave and lotion when you are done. I will finish putting things away."

"Thanks, and please pick out what I am to wear tonight," I replied as I headed for the shower.

By the time I came out of the bathroom after I had showered shaved and putting on lotion, Julie was dressed. She had on a black mini dress with a sheer top that left areoles and her erected nipples clearly visible. She was also wearing a pair of black-ankle-strap sandals and she looked stunning.

She had my clothes laid out on the bed. The wasn't much there; a pair of pink high-heeled sandals, pink nylon anklets with a ruffled crop-top and short lace trimmed mini skirt with narrow lace suspenders. Julie sat me down and did my make-up and combed my short hair in a unisex style, commenting, "You will need to learn to do your own make up and I can't wait until your hair grows out and we can get it styled."

I got up and got dressed putting the socks on first then the dress. Julie helped with the suspenders as she threaded them through my nipple rings before adding a bell to each ring. I stepped into the sandals and Julie locked the ankle straps around my ankle. The skirt was just long enough that it covered my clitty if I was careful. Then I slipped the top over the suspenders and as I suspected it barely covered my nipples let alone my breasts.

Julie said, "Nora bend over the bed, raise your skirt and reach back and spread your ass checks." I did as she requested as she slipped a latex glove on her right hand. She grabbed a butt plug and a bottle of lube and proceed to insert the plug in my ass. She used the attached pump to blow up the plug. After this she detached the pump leaving the plug enlarged and had me stand up. It took a little bit to get use to the plug and I walked a little bit funny with it inserted. I also noticed that there was a short wire hanging out the end of the plug.

Julie grabbed a leash and attached to the ring on my collar and we started off for the dining room. As we were walking the butt plug started to vibrate a little. Then the vibrations increased and changed rhythm of the vibrations. Julie turned to me and said, "How do you like your little toy, Love?"

I replied, "It is interesting and a little distracting."

On the way there we stopped by the front desk and Julie made an appointment for the two of us at the beauty salon for 9:00 in the morning.

When we arrived at the dining room, Barb and Butch were waiting for us. Barb was dressed in a black halter-top mini dress and black high heels and looked amazing. Butch had on a black jock strap with his tail plug inserted and he had mitts on his hand miking it impossible for him to grip anything. Butch was kneeling beside Barb's chair like a good dog. I noticed that he had to be one of the hairiest men I had ever seen. He had hair covering nearly all of his body and it was thick, almost like a werewolf. The masked had been removed and I noticed the end of his nose had been tattooed black and his ears had been modified to points like a Doberman pincer.

Julie walked around to where Barb had stood-up and gave her a light kiss that was returned. The three us sat down while Butch laid down beside Barb. Julie and Barb talked about the resort and we found out that this was Barb and Butch's sixth trip to the resort and Barb offered to show us around tomorrow afternoon. Julie told Barb about herself, our recent marriage and plans. Just as she was finishing a waitress came to our table and took a drink order for the three of us. After she left Barb said, "Butch is not allowed alcohol but gets a special treat. Butch, give me your drink bowl."

Butch picked up his plastic drink bowl with his mouth and handed it to Barb who said, "Normally I would fill it here, but because of the dining room restrictions we better go to the restroom. Julie, would you like to accompany me?"

"That would be a pleasure. Nora, you stay here and keep Butch out of trouble," and the two women headed off to the restroom with Butch's water bowl in hand. They returned a short time later with the bowl full of liquid and set it on the floor by Butch. Julie would tell me later that Barb had explained that the only liquids Butch was allowed was urine and a bottle of water first thing in the morning and at night. When they got to the restroom, Barb asked Julie if she would like to fill the bowl, which she did, so butch was getting a treat. Butch started to drink his drink as the waitress brought our drinks.

We started to nurse our drinks and Julie, turned to me and said, "Nora while we are here at dinner during the honeymoon you can feel free to join into the conversations. When you do, make sure you address and dominate properly.

"Thank you, Mistress."

With that Barb started to tell us about herself and Butch. We learned that Barb was fifty-one and Butch about two years older. They were both bisexual, although Barb more so than Butch. She had caught him cheating on her about five years ago and she gave him a choice of leaving the marriage penniless or become her pet bitch. He would spend his days naked on his hand and knees. The hand mitts would be on all day and removed only at night when his hands were secured to prevent him from pleasuring himself. The tail butt plug would be inserted at all times except when defecating or involved in anal sex. She said he agreed, and it started out as weekends only but over the first eighteen month he turned into a fulltime pet.

Through our kinky activities I met a doctor who helped develop a drug regimen that resulted in extra body hair growth that you see. It works well and had only one drawback, it also enlarged his cock, which has been modified, and made him continually aroused. There were pluses to this, but also drawback. If I did not control his actions, he would be trying to get relief right now, even if it was only by humping your leg.

"Wow, that unbelievable," responded Julie, "How do you control him?"

"Butch sit up," said Barb and the dog sat up on his haunches with his front paws up, like a dog begging. Barb reached down and pulled his jock strap down long enough for us to get a quick look. It was the first chance Julie, and I got a chance to get a good look at Butch's cock. His cock was soft, and completely withdrawn into its skin case. but even that was at least eight inches long. He had not been trimmed and part of the length of his penal skin had been surgically attached to his belly, like a dog. His cock when soft was fully encased in the skin tube. Barb explained that his cock had also been modified so that when erect it was nearly fifteen inches long, but rather slender and the head pointed similar to a dog. When it gets fully erect a bulb forms about 6 inches back from his cock head, just like the knot on a dog's cock. There was a band around his balls, that had an elliptical orb attached to the back of the band. Barb let the jock strap slip back in place, just as our waitress arrived to get us a refill on our drinks and take or dinner order. The three of us order sea food dinners and Barb ordered a doggy bowl for Butch.

After the waitress brought us our drinks, Barb continued talking about Butch. The small orb is the control package for the sheath. It has rechargeable battery, micro compressor and other electronics. The battery lasts about 18 hours on a charge. There are contacts in the band that allowed Barb to shock Butch's balls if he got out of control. She also explained that they modified the head of his cock so he can fuck for hours before he gets enough stimulation to ejaculate. You might want to consider trying Butch sometime?"

I could tell Julie was getting turned on listening to this as she said, "That sounds great and I might take you up on the offer."

Our meals arrived and Butch ate on the floor out of his bowl and the conversation turned to other things. All through drinks and dinner, Julie had been teasing me with the butt plug, turning it on and off, up and down, vibrating, thrusting or both. She was keeping me well aroused, for what I did not know. After we finished our meal, we moved to the bar to have a drink before heading to our cabin. Since it was now after 8:00, Barb removed Butch's jock strap and took him for a short walk on the way to the bar so he could relieve himself if he needed.

In the bar the three of us got a table and Butch settled down next to Barb on the floor. A waitress approached our table to take our order. She was about 5' 10" tall in her high heels and wearing dark pantyhose, a short black mini skirt and a sheer white blouse through which her areoles and nipples were clearly visible. She took our order and then walked away from the table. Julie couldn't keep her eyes off the waitress' sex ass, which both Barb and I picked up on.

"Julie, did you like what you just saw?" asked Barb.

"Yes, she is very cute."

"Are you aware that some of the staff is open to playing with the guest, when not on duty?"

"No, I was not aware of that. How does it work?"

"The staff for the most part stays in staff housing here at the resort, but they are not allowed to take guests to their quarters. If a guest and a staff member want to get together it has to be in the resort area or the guest cabin."

"But how do you know if the staff member is open to playing?"

"When our waitress returns look at her name tag. If there is a green star in the upper right corner the staff member is open to playing. A star or stars in the lower right corner indicated other information: blue indicates straight, red indicates gay/lesbian, purple indicates transgender, pink indicates submissive, grey a switch and black dominate."

"Thanks, Barb."

Barb just finished her explanation as Anna, our waitress returned. All eyes we on her name tag which supported a green and red star. We explained to Anna that we were calling it an evening and Julie signed the check charging the drinks to our room. Julie stood up to return the check to Anna and whisper something in her ear; to which Anna nodded affirmatively.

We then said our good nights to Barb and Butch and headed for our cabin, with Julie leading me by my leash. All during the ten-minute plus walk to the cabin Julie kept me aroused playing with the controls of the butt plug, more vibrations, thrusts, pulsing vibrations, etc.

We got to the cabin where we both removed all of our clothes and I stood there waiting for Julie to tell me what to do, when she asked, "Would you like to cum tonight?"

"Yes, Mistress I would enjoy that very much."

"That is a good answer sissy, but it will cost you some training first."

"That is OK, Mistress, what would you like me to do?"

"Go into the shower and turn it on the water and get it all warmed up and I will join you in a minute." I went and turned the shower on and noted the size of the shower, it had two heads and would easily accommodate four people. Julie joined me a few minutes later and said to turn the water to warm at a low flow rate. She then instructed me to lay down on the shower floor.

"Sissy, you know urine straight from the human body is sterile, unless the person has an infection. That being said one of the greatest signs of servitude and respect a sissy can show his Mistress is to accept her golden nectar. Are you ready to receive Mistress' gift?"

"Yes, Mistress."

Julie stood over me with a leg on each side and squatted down as I looked up at her beautiful body. She reached down and spread her pussy lips and let a stream of hot piss escape striking me first on my clitty and then she aimed it up my body finally hitting me in the face.

"Open your mouth sissy and taste my gift."

I opened my mouth and got my first taste of her golden nectar. I was slightly acidic and bitter, but overall, not bad. When she finished, she turned the water up and removed butt plug which had been vibrating and pulsing during the golden shower. Then we washed each other before drying and returning to the bedroom in the cabin. Julie put cuffs on my wrists and connected them with a thirty-inch chain behind my back before having me lay down on the bed.

The first thing she did was check all of my piercings and add some first aid cream to each. Then Julie said, "Time for your reward!" With that she unlocked my clitty and covered it and her hand with some lube. She slowly started teasing my clitty eventually stroking it. Over the next hour she brought me to the edge numerous times without letting me orgasm. Finally, she brought me to an orgasm but immediately stop stroking ruining the orgasm, as I madly thrust my clitty in the air. After I had finished shooting my cum all over my stomach, Julie grabbed my clitty again securely holding the shaft she started rubbing the super sensitive head of my clitty with her other hand. I started thrashing around trying to get away from the intense pain/pleasure of the post-orgasm torture.

Once I had calmed down and caught my breath, Julie locked my clitty to the ring in my scrotum. She then climbed up on the bed and lowered her wet pussy down on my face saying, "Now it is my turn, sissy. You better give me a good orgasm." Knowing what she enjoyed I started slowly and gently kissing and licking her pussy. Slowly I increased the pace and pressure until Julie exploded in orgasm, soaking my face in her sweet juices. Julie moved off my face laying down beside me and giving me a kiss saying, "Good night my sissy slut."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Sissyboi44Sissyboi445 months ago

Can’t wait for the next chapter!

4Leather4Leather9 months ago

Love the kinky resort. Not totally into few of the things you have going on. Love to see chapter sex to see what you have planed.

AnonymousAnonymous10 months ago

I am loving this series so so much I cant wait for chapter 6 ,I do wonder if the resort is looking for new staff, I would love to work there as a sissy maid/waitress. Write again soon x sissy Lucy

AnonymousAnonymous10 months ago

not a fan of the dog and urine stuff but still an interesting premise of being at a resort

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Marrying into Femdom Culture She brings him home, shows him how women like her love men.in Sci-Fi & Fantasy
The Bet A sucker bet turns husband into a suckee.in Transgender & Crossdressers
Comforting Pete Consoling friend reluctantly agrees to help in other ways.in Transgender & Crossdressers
How a Wife deals with a sissy An intense short story of Cuckoldry.in Transgender & Crossdressers
Caught A married couple experiment with femdom, with a little help.in BDSM
More Stories