A Proposal

Chapter 4: A Proposal

This is the continuation of a true story of my wife, Jan, and my relationship and how we got caught-up in a sexual role play situation. We started out with Jan playing the part of a hooker and me playing the part of a john. She was however picked up by one of the management personnel at her place of employment and this led to her becoming his escort and having sex with him for money. She finally ended up spending the night in bed with him and this is where we stopped the last installment due to its length and the turning point that this was in our sex lives.

Jan and I were laying in bed, she was clad in only a lacy blue bra, which she had unclasped and was laying opened at the sides of her pert breasts, and a matching lacy blue g-string, that was soaking wet with the results of her coupling with Mr. Chuck Hassek, a vice president of the company she worked for as a secretary. The g-string had been pulled off to the side of her pussy by me and I was busy kissing and licking her puffy, and used, pink-lipped pussy. Jan was lying with her tanned thighs spread apart on our bed and was relating to me the events of the evening in her new role as escort. I had listened patiently for her to tell her story but my lust and jealousy had grown and I was now urging her to tell me more about the hot sex she had just had with her john.

“Chuck and I were cuddling in bed, face-to-face, looking into each others eyes, and he was softly kissing my neck and stroking my hair and my breasts. He would pinch and tease my nipples a bit and then run his finger slowly around the pebbly tip. I was starting to feel myself becoming aroused again from his touch. I had my fingernails lightly scratching his chest and his man-nipples, which were erect from my touches. He and I were talking softly and I was feeling warm and relaxed.

“So Jan, have you thought about making this real?” Chuck asked in a low deep voice as he ran a finger up my neck, his eyes locked onto mine.

“Making what real Chuck?” I replied with a question. I wondered where this conversation was going. Chuck’s finger now slid around my chin and under my bottom lip.

“Becoming an escort. Being a real prostitute. You would be very good and Justin would like it, I know.” I was surprised by his words and I waited a few seconds before I responded. My fingers had stopped their movements on Chuck’s chest.

“And just how would I do this?” I asked in a teasing manner as I wondered if this was a form of verbal foreplay for Chuck.

“There are two ways I have in mind. I know a woman who operates a small exclusive escort service and I know she would love to hire you. It would be a lot safer than playing as a street whore and I’m sure Justin would approve.” He spoke these words with sincerity and it shocked me.

“I don’t know Chuck. This is fun with you only you. You mentioned another way?” I was intrigued by his line of thought and was feeling a little more stimulated by his suggestion and thought, why not play along.

“You could work for me. I know some men who would pay top dollar for a roll in the sack with you. I would set it up and you could make 5 or 6 hundred a night. Real high-class action only.” He replied his fingers now pinching my nipples gently.

“That sounds really exciting Chuck and I think I should be flattered but I don’t want to be an escort. I only want you for a client and that alone turns Justin and me on.” I answered thinking that it might be fun to try it sometime.

“Really Jan, this could be a great opportunity to sleep with some powerful men. You could try it a few times and see what you think.” Chuck was now pinching and turning my nipples and I was becoming more playful due to his touches.

“No Chuck, I don’t want to sleep with some powerful men. Justin and you are just fine for me. Umm… that sure feels nice when you do that.” I turned down that offer but was thinking that his fingers were making an offer of a different nature.

“I am glad you like this. Why don’t you clean me up right now?” Chuck asked as he sort of glanced downward towards his groin area.

“I had that in mind too; let me go get a warm washcloth.” I responded as I attempted to pull away.

“No, with your mouth.” He ordered as he locked a stare right into my soul.

I slowly uncoupled from him and slid downward on the bed until I was directly examining his penis. It appeared to be slumbering against his thigh, softly drawn-up into itself. It appeared to be sugar-glazed as it was coated with whitish mixture of his sperm and my juices. They had dried all over his cock and his balls. I hesitated for just an instant and then I opened my mouth and let my tongue slip from it.

I began by licking the head of his deflated manhood with my tongue. He tasted musky. The texture was rough at first from the dried coating but the saliva from my tongue softened the coating and I tasted the results of our coupling. I licked the head all around and then opened my mouth to take his still flaccid shaft into it. I sucked and licked his cock. My mouth watered from the taste and the nature of this act. I was not only playing the part of a whore, I felt like one too. Lapping up my juices and cleaning the spent cock of my customer.

“Jan that is so nice, your mouth is so warm and soft.” Chuck mumbled as I felt his hands stroking my hair in a gesture of closeness.

I nestled down into his pubic hair, his entire cock in my mouth, my tongue licking and flicking the sleeping serpent. I pulled his cock from my mouth and licked downward to his balls. They appeared to have almost a ring of crusted matter on them. It felt lumpy and crusty as my tongue softened it and then licked it up.

“I was hoping that you would accept my offer to be an escort. I thought that you would want to play the role of escort for a while. I just figured that if you asked Justin that he would encourage you to try it. He would really be excited about you doing this with other men.” Chuck spoke as I cleaned his cock.

“I’ll bet that Justin will want to get down and lick your slutty pussy when you get home won’t he? Eat all of my cum from your nasty hole.” Chuck’s cock began to stir as he spoke and I could feel little movements against my face as I tongued his balls.

“I know he sniffs and licks your panties after you date other men doesn’t he? Have you ever caught him sniffing your soiled panties?” Chuck’s voice became huskier as he spoke these words or so it appeared from my vantage point under his balls.

“Jan, lick all the way to my asshole.” Chuck ordered as he spread his legs and I moved to area below his balls but not to his ass. The hair that was between his legs was matted with the dried mixture of our two bodies. I licked at it and sucked some of it into my mouth. I was feeling very nasty and dirty as I continued to lick and clean him. I was feeling demeaned and I wanted to get up and shower. I wanted to wash the filth from my face and hair. I slowly continued my oral ministrations on my first john. I was thinking about how this must look to Chuck. He was really getting his money’s worth from me now. I licked lower but avoided any contact with his anal pore. Chuck seemed to notice this because he called it to my attention.

“Jan, clean-up my asshole too. Lick it all clean.” Chuck commanded his whore.

I tentatively licked at the brown, hair fringed anal opening. I was disgusted and I pulled myself up and slipped my mouth over Chuck’s cock which appeared to have gotten firmer over the last few minutes. I began to blow Chuck’s cock.

“Um…that is so nice my whore. You seemed to have missed tossing my salad, but I don’t mind, this time.” He chuckled as I felt him grow harder against my tongue.

Chuck reached down under my arms with his two hands and pulled me upwards until I was again facing him and we were looking into one another’s eyes. He appeared to enjoy the look of smeared lipstick and submission that I knew was all over my face. He kissed my lips gently and I knew he tasted us in my mouth.

“Jan, I have another proposal for you that I feel is one you might accept but first, I want you to know that I am glad that you turned down my offer to work as an escort. It would have been nice and it would have worked out very well for all of us but because you turned it down, it makes this offer possible.” I had no idea what Chuck had in mind and I reached down and began stroking his cock.

“Jan, as I said before, I know that Justin is a boy that appreciates the scent of your soiled panties. I’ll bet he has jacked-off with many pairs of them. I also know how great your pussy smells so I don’t blame him.”

“I don’t think so Chuck. Justin has never sniffed my undies.” I answered as his cock twitched and grew in my hand.

“How do you know that Jan? Have you ever asked him? I’ll bet you that if you try you can watch him sniff and lick the crotch of your panties.” Chuck boasted as he began to palm my breasts. I was again feeling horny and I felt my already wet pussy moisten further.

“No I have never asked him. That is disgusting. Justin can sniff and lick the real thing anytime he wants to.” I replied anger rising in my voice.

“I seemed to have touched a nerve, Jan. Now here is my proposition for you.” Chuck smiled and looked deeply into my eyes again. His hand movements had increased to a milking motion on my boobs. I looked deeply into his eyes and sighed heavily from the electric feelings cursing through my breasts every time he pulled them towards him. He appeared to be not just milking them but kneading them like bread dough.

“I no longer want you to be my whore, my escort. I want you to agree to be my mistress. Now before you say anything, just hear me out.” Chuck’s words almost slapped me due to the nature of the discussion.

“Chuck, I am happily married to Justin and I love him very much. I could never even consider leaving him.” I explained as I felt my nipples bulge outward as Chuck kept milking my boobs.

“No Jan. I know you are happily married and I know that you love Justin very much. That is why I made this offer. I don’t want you to leave him and I don’t want you to love me. This is another business relationship between the two of us and I am absolutely sure Justin will jump at the chance for you to be my mistress.” Chuck was still looking deeply into my eyes and he was continuing to stimulate me. I was panting as he spoke to me.

“Here is the arrangement. You and I will get together just like we did this Wednesday night but we will also get together every other weekend, and also at least a couple of vacations a year. You will be my companion and mistress on a part-time basis. I will pay you 500 dollars a week and buy you nice clothes and gifts. I will take you on my boat and trips to exciting places.”

“But Chuck…” I interrupted and I also was starting to pump his now fully erect cock.

“Please Jan, let me finish. You and I will no longer be whore and customer but mistress and boyfriend. We will be in an entirely different relationship. I will treat you like a queen and you will travel with me, go places on my arm and of course we will continue to fuck and suck as much as possible.” Chuck finished his proposal and smiled at me. I didn’t know what to think initially so I quietly played with his manhood. “Chuck, that sounds great, I mean I am flattered but I would have to ask Justin. I am not sure. I need to think it over.” I answered. Chuck smiled a broad smile and then said.

“Jan here is a little wager. I’ll bet you that Justin will want to eat your pussy when he hears that it is filled with my spunk. But here is the wager. If Justin sniffs and licks the crotch of your little g-string there, then you have to spend this weekend with me on my boat at Saugatuck starting Friday evening, if not then you guys just plain sit down and make your decision.” Chuck now had my attention; he also had both of my nipples in his finger tips and was pinching them and twisting them harder than he had before. I liked the way it caused my nipples to burn and ache.

“Okay, Chuck, I’ll take your wager.” I grinned back at him and ran my fingers of my right hand over the head of his cock which was now lubricated by his pre-cum that had oozed from the little slit on the top of it.

Chuck continued to pinch and twist my nipples and this eventually caused me to cry out from the pain. He smirked and backed off a little from the pressure level that had hurt me. I tried to pull back but he held by my nipples. Chuck then told me that he wanted to fuck me doggie style and he had me kneel at the top of the bed with my hands on the top of the headboard of the bed. I complied and he came around behind me to begin his coupling.

“This is how the stud dog mounts the bitch in heat. Are you my little bitch in heat Jan?” Chuck asked as his cock nuzzled at the entrance to my pussy. I felt his cock prodding at the lips of my cunt and I spread my kneeling thighs further apart to accept his big cock.

“Mount this bitch. I am your bitch in heat, my stud dog. Fuck your bitch hard!” I exclaimed as his cock found its target.

Chuck’s hard cock slipped easily into my very wet and very ready pussy. It slid almost entirely into me on his first stroke. I held on tightly to the headboard and wiggled my ass backwards to assist Chuck’s complete entry into my pussy. He thrust his hips hard and his thighs slapped against my buns, he was in me completely.

“Oh my big dog, fuck me hard. God that feels so great!” I exclaimed as he began humping me.

Chuck began a hard pumping motion while his hands gripped my hips roughly. He stuffed his cock into me with hard strokes. He would pull his cock out of me until only the tip remained inside of my pussy lips then he would grab on to me quite roughly and slam his cock all the way back inside. It felt wonderful and I was falling into his rhythm. I squeezed my pussy down onto his cock with every stroke. I moaned and sighed; calling Chuck’s name every time I felt the beginnings of my orgasm. Chuck stopped stroking and withdrew almost the entire length of his cock from my love tunnel.

“Okay bitch, you do the work now.” He ordered. Chuck held his cock at the entrance to my pussy and made me push myself back onto his hardness. I would slide him completely into me then I would pull myself back off from him. I was doing all the work of stroking his cock with my pussy. On every stroke I would squeeze and milk his cock for him. He was grunting and huffing from my efforts and I knew he couldn’t last much longer. I also knew that I only needed a few more of his strokes and I would be enjoying my pleasure.

Chuck leaned over on to my back with his body on my next backwards stroke. His arms reached around until his hands found my breasts. His fingers found their target; my nipples, and he started pinching and rolling them. He began humping very deliberately into my quivering pussy. I was wide open to his cock and I could feel the ridge along the top of it. It felt so wonderful and so filling. I started to cum; he heard my squeals and pinched both of my nipples harder. I arched my back and with one final thrust he buried his cock in me and held on tightly as I thrashed about underneath him.

He was unmerciful with his pinches and I opened my mouth and loudly wailed as my orgasm washed completely over me. I squealed, I screamed and I came completely. Chuck’s cock was spasming into me as he came and spewed his seed deep into my belly. I wanted this feeling to continue on and on as I had a series of small orgasm from his cock. Finally, we collapsed onto the bed. Chuck holding tightly onto my nipples with his fingers, his teeth buried in the nape of my neck, and his cock lolling around in the wetness that we had created. My pussy felt like a swamp as we jerked and sighed together.

We must have drifted off into a post-coital slumber because we both awoke with a start as the clock radio beside the bed began playing music. I glanced at the illuminated numbers on its face, 1:30. Chuck stirred and snuggled closer to me. He was behind me, holding me in a spoon position, his spent manhood lying in slumber between my buns. It felt wonderful and I was wishing that the moment wouldn’t end.

“Clean me up Jan and then we should head on home.” Chuck suggested as he unwrapped his arms from my body. I began to slide down his body to take his used and sticky member into my mouth when he stopped me.

“No honey, how about a warm washcloth this time, and bring two, so I can wash you too.” He corrected me with a tenderness I had not expected from him.

I got out of the big king-sized bed and went into the bathroom. The vision in the wall- size mirror scared me. I looked a sight. My hair was tangled and tossed; I looked like I had been through a storm. My makeup especially around my eyes was smeared and messy. I looked horrible. I sat on the toilet and felt the spent remains of Chuck’s cum drip from my contented pussy. I spread my self wide so that as much as possible could run from inside of me. I knew there would be plenty there for Justin’s creampie that he would be home waiting for me to bring to him. My body appeared well worn and bruised from our animal-like sexual activities.

I brushed my hair, washed my face and reapplied a bit of makeup. A quick spray of cologne and I walked out to Chuck’s slumbering body lying underneath the covers of the bed. I gently touched his shoulder and quietly whispered to him; so as not to startle my sleeping lover.

“Chuck, Chuck sweetie. Here let me wash you up.” I called as I slipped into bed beside him.

Chuck stirred awake and I began gentle cleaning his totally spent cock and balls that were coated in a drying film testifying to our recent actions. The cock that had once pleasured me looked again like a slumbering serpent as I finished cleaning and examining it. I lay back so that Chuck could cleanse my pussy that he was now closely examining.

“No, Jan, it would be best if you left your slut cunt filled with my cum so that Justin can clean you properly with his tongue.” Chuck said as he began to search for my panties.

“You should probably put these on soon so that Justin won’t lose any of the creamy treat that I left inside you.” He recommended as he twirled my g-string on his fingers with a sly smile.

We both slowly dressed between kisses and hugs. Chuck seemed to take great pleasure in watching me dress and putting myself into order. He also liked to play his fingers over my thighs and buns as I stood arranging my clothing into a presentable state. I helped him pull his boxers on and kissed the tip of his cock just before I hid it with his underwear. After we were finished dressing we stood in a tight embrace at the entry to the hotel room. We kissed and our tongues entwined once again. Chuck could not keep his hands off from my butt and I feared that we would soon be tugging our clothes off from one another again.

“Here Jan is another hundred dollars. You were great and I thoroughly enjoyed myself with you my whore.” Chuck said with as he handed me the money. I immediately felt cheap and trashy. He never failed to make me feel like a slut. I took the money and put it with the rest of the cash he had given me into my purse.

“Thanks Chuck, the pleasure was all mine.” I replied trying to manage as genuine of a smile as I could through my humiliation.

“About my offer, think about it seriously. It will be entirely different with us, trust me.” Chuck directed as he attempted to make me feel better about myself, at least I thought so.

“Why don’t you leave your soiled panties lying around where Justin can find them and you can watch him fondle and smell them, you will see that I am right?” He teased as he opened the door to the room and we walked into the softly lit hallway. We walked arm and arm to the elevator. Chuck kept his arm firmly around my waist and held me close to him. In the elevator he kissed me and caressed my butt underneath my dress. Chuck appeared to enjoy feeling my body with his fingers. Just before the door opened he cupped my mound through my panties and squeezed. I could feel myself becoming aroused again.