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First Time
21/06/2018
How many times have you set something into motion that you knew you might regret? This was one of those times. i finally sat down with my wife and told her of my desire to experiment with cuckolding. She knew that i sometimes liked to lock my cock into a chastity cage. Now i was about to tell her that i wanted to invite another man over to fuck her while i watched and maybe joined in. And that is what i did.


i told her that we were going to go out tonight for dinner, some drinks, and maybe some dancing. i also let her know that we would spend the night in the Crown Plaza in case we drank too much. i asked her to dress sexy.


She came out of the bathroom looking very sexy. She had chosen a black dress with a low neckline and black 4" high heels with black nylons. i just loved her makeup. It was exotic with a lot of attention to her eyes. Lots of mascara, eyeliner, and eye shadow. To top it all off she had applied a deep red lipstick to her lips.


"You look fabulous!" i told my wife. "We should not have a problem finding a man to fuck you silly. And i hope to be able to watch and help."


"Yeah, let's talk about that. How much interaction and contact do you want to have?" my wife asked me. "I know that you are submissive. Do you want me to play the role of your Mistress tonight?"


"That would be great, Mistress." i replied. "As to interaction and contact, i leave that up to my Mistress. All i desire of this evening is that you are sexually pleased. i will do whatever you ask of me to reach this goal. i do want to be able to watch or hear you and your partner."


"What if i want you to get his cock hard for me?" you inquired.


"You are my Mistress and i will do whatever you ask. If you ask something that i have no problem doing with then my response will be simply 'Yes Mistress'. If you want an act that i have a little aversion to i will say 'If it pleases you, Mistress.' If it is something that i absolutely do not want i will say 'Please don't make me do that, Mistress.'"


"All right. That sounds like it will work. Now go and lock your cock up in a chastity and bring me the key." She responded.


i quickly went and did as Mistress requested. When i came back into the room, i handed her the key. She put it on a necklace and fastened it around her neck. "This is so you will remember that I am in control. Show me your cock."


i lowered my pants so she could see that my cock was secure. "Put your hands behind your back." you ordered. i quickly complied as you stroked my penis. i had chosen my lock that used my PA piercing. The head of my cock and half of the shaft was encircled by the cage. i could get hard but could not come. It was the most secure and the most comfortable chastity that i had. You played with me until i did get an erection. "I think that i would prefer you in a cage that would prevent you getting hard, but I will allow this tonight. Just remember that your orgasm is not your goal."


"Yes, Mistress." i answered.


"What is your goal tonight?" you asked. "And what should i call you?"


"My goal is your pleasure with or without me, Mistress. And please call me cuckold." was my answer.


"That is correct, cucky. Now, let's go to the hotel and check in."


We left and drove over to The Crown. i checked us in and we went up to our room. It was after 7:00 and we were both hungry. "Would Mistress want to go down to the restaurant for something to eat?" i asked.


"Yes, cucky, i do want to go to dinner. But before we do that there is something that i want you to eat. Kneel here in front of me and eat me to orgasm. Hopefully not my only one tonight." you ordered.


i knelt and you raised your dress to show that you had a garter belt holding up your stockings and did not have any panties on. "It has been quite a long time since i had had the pleasure of this. Thank you Mistress." i went right to work. After about 5 minutes you came loudly and wetly. God, i loved drinking your juices.


We left our room and went down to the restaurant where we had dinner. Mistress turned some heads around as we entered the room. She looked very lovely and she was showing a lot of leg and boob. We had a very nice and leisurely meal. Mistress had a mixed drink with the meal while i was restricted to water. After the meal we went to the bar for an after dinner drink for her.


We sat at the bar next to a gentleman who looked to be there alone. Mistress said hello to him and introduced herself. He looked over at me and asked "And who is this?" Mistress looked at me and said "Tell him."


i looked past Mistress to him and said "i am her cuckold, Sir. We came out tonight in hopes that i could find a man to make love to her. Would you be interested?"


"Of course I would. She is very lovely and oh so sexy. You are a lucky cuckold to have one this beautiful." Then he turned to Mistress and said, "My name is James. What is your name?"


"Please call me Jasmine for tonight. Are you here by yourself?" She inquired of James. He was about 6'0" and maybe 200 lbs in his late forties with gray in his hair at the temples.


"Yes I am alone. I am in town on business and am here just for the night. I would consider myself blessed if I could be the one to make love to you this evening." said James now ignoring my presence.


"You are the first man that I have seen tonight that I have interest in. That is why I sat next to you." i watched as you rested your hand on his knee and ran it up the inside of his thigh. You stroked his thigh multiple times as you talked of the possibilities of the evening.


"You are having an effect on me." said James as he reached down and laid his hand over yours and pulled it up to his crotch. He then leaned in for his first kiss of the night. Mistress accepted his kiss and returned it. i saw that her hand was fondling James' cock through his pants. His hand snaked its' way up Mistress's leg and when it reached her bare pussy he broke their kiss and said "Oh my. This is wonderful."


They kissed and played below the bar for about 5 minutes until James said "I have to have you. Do you have a room here?"


"Yes, I do. Cucky, go to the room, turn down the bed, get naked, and get on your knees. We will be up after we finish our drinks." Mistress stated to me. i left the bar.


"'Cucky'. I like that. And what will Cucky's role be during our encounter?" asked James.


"Any thing that I want it to be. At the very least he will have to watch you make love to me. If you don't mind, I would like to have him place your cock at my hole." She said as she squeezed his slacks covered cock.


"This hole?" inquired James as he slipped a finger deep inside Mistress.


"Oh God yes. That is the one." And James added a second finger. "That feels so good. Don't stop James." James placed his thumb on Mistress's clit and pistoned his two fingers in and out of her pussy. "You've got me hot now. I want your cock, James. Cucky should be ready for us as our room is on this floor. Let's go." James removed his very wet fingers and left money enough for both of their drinks on the bar.


They were at the room in no time at all. Mistress opened the door and as soon as they were in the room the door was closed and locked. The bed covers were turned down and i was nude and on my knees at the foot of the bed.


"It looks like Cucky follows your orders well. Will he follow mine too?" asked James.


Mistress looked my way and said, "Do whatever James asks. And you may refer to him as 'Sir'"


"Yes Mistress. Sir, is there something i can do for you?" was my response.


James walked over to me and stuck his two fingers under my nose. i could smell my Mistress on them. "Open your mouth and clean these for me." i opened my mouth and sucked them clean. "Now take my clothes off." i untied his shoes and slipped them off then i stood and unbuttoned his shirt and removed it. "Who told you to stand. Back on your knees, Cucky." i quickly knelt in front of him again and reached out and unbuckled his belt and then i unzipped his pants. i slid his pants and underwear down his legs. His half hard cock came into view. It looked fairly impressive.


"Cucky, finish undressing James and bring that cock over here. But not until it is completely hard." i looked over and saw that Mistress was out of her dress and laying on the bed in hose, heels, and garter belt. She looked luscious. i started stroking James in an effort to harden his dick but my hand just was not doing the job. "Cucky, I want that cock now. Suck him and he will be ready."


"Yes Mistress." was my answer. i opened my mouth and sucked James into my mouth. In no time at all he was rock hard. James took his erection from my mouth and crawled across the bed to Mistress. He straddled her body on hands and knees with the head of his 7" cock pointed at her opening.


James then said, "Cucky you have one more job to do. Guide my cock into Jasmine's pussy." i got onto the bed and grasped James thick cock. i lined it up with Mistress's ready opening and rubbed the head across her lower lips and then placed it where all James had to do was push.


"There you are Sir." i informed James.


He easily slid his entire length in my Mistress making her moan out loud. "Oh, does that ever feel good. Cucky you can make me feel this good if you just add another inch or two to your cock. Fuck me good, James. Show my cuckold how it is done." And i watched from just a couple of feet away as they fucked.


"James, stop for a minute. I want you to fuck me doggy style." James got up off of Mistress and she also stood up. "Cucky, lay on your back on the bed." Mistress then got on her hands and knees with her pussy directly over my head. "Now put your cock back in my pussy James." i watched as she took James's cock again. His cock pistoned back and forth in Mistress as she moaned and moaned. After many minutes Mistress moaned that she was close to coming and commanded me, "Cucky, lick and suck my clit until i come." i quickly fastened my lips onto her clit and rolled it in my mouth. She screamed and gushed as her orgasm hit her. i opened my mouth and drank her fluids down.


James waited for my Mistress to come back to earth but did not remove his cock. i reached out with my tongue and lazily licked some of Mistress's come from his balls. "Mmmm, that feels good Cucky."


"What is he doing James?" Mistress asked.


"He is giving my balls a tongue cleaning and i really like it." James told Mistress. "You are the first woman I have ever had who is a squirter. I liked that too."


"Would you like to have him suck your cock a little while i rest?" asked Mistress.


"That would be great Jasmine." replied James.


"Cucky, open your mouth and pleasure James for a while."


James removed his cock from Mistress. It was dripping with her moisture. i fastened my lips over the head of his hard cock. i sucked on the head and then took a couple of inches into my mouth. i worked on this and then took a few inches more. It was wonderful. i finally took his cock until the head hit my gag reflex. i then swallowed the rest until my nose bumped into his belly. James had a perfect cock for me. Just the right length to test my limits.


All this while Mistress was on all fours with me under her. It felt like James was getting close to coming and that is what he told Mistress. "Stop sucking him. I want his come in me. You stay right there, Cucky. James, I am ready for your cock again." James removed his erection from my lips and plunged into Mistress's hole just above my face. It did not take long for James to get there. i watched as his balls tightened and his cock pulsed jet after jet of come into my wife. She screamed and came again. My face was drenched with her ejaculate again.


After a short amount of time, James pulled his softening cock from Mistress. His cock head was laid on my lips along with his request of "Clean this for me cuckold." i opened up and took him into my mouth one last time. i cleaned their combined juices while Mistress dripped more onto my face. James, who had removed his cock, said "Now you had better clean your Mistress." Mistress lowered her gaping pussy to my waiting lips. i reached out with my tongue and scooped James's seed into my mouth. While i was cleaning up the mess, Mistress came one more time and deposited their combined fluids that i could not reach.


Mistress rolled off of me and we both could see that James had gotten dressed. He came over and gave Jasmine a deep kiss and thanked her for a great fuck. He then let himself out the door.


"Wow! Was that a great fuck or what." exclaimed Mistress. "Did you enjoy yourself Cucky? It does not really matter if you did or didn't because I sure did. Did you bring your bondage toys?"


"Yes, i did Mistress. They are in the blue duffel bag." i answered. You got up off the bed and opened the bag. You tossed the wrist cuffs and blindfold to me and told me to put them on. i buckled the cuffs on and slipped the blindfold over my eyes and laid on the bed in darkness. i heard you get dressed and the sound of a chair being moved.


"Come sit on the edge of the bed Cucky." you ordered. i sat up and moved to the edge of the bed. You grabbed my arm and pulled me up. You then led me over to the chair and told me to sit. You then fastened my cuffs together behind the chair and secured my ankles. Mistress then stated, "I wasn't sure if I was going to like your idea of being the cuckold but i certainly did. Now I am going to go back to the bar and see if I can find another man to cuckold you. See you later, Cucky."


END OF PART 1


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