Beyond Sissy's Spa Day Ch. 07

Story Info
Sissy faces decision of a lifetime.
6.3k words
4.63
30.8k
18

Part 7 of the 7 part series

Updated 06/09/2023
Created 02/03/2019
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
danni5858
danni5858
144 Followers

This is the seventh and likely final installment in the "Beyond Sissy's Spa Day" series. The stories make much more sense when read in order.

*****

It is 100 percent safe to say that I had never experienced a Saturday night like this.

While I had always known that weekend nights were the most popular times for people who actually fucked to do the big nasty, I had rarely been involved in anything like that. And when I say rarely, I mean as in practically never. Able to count the number of times my little dick has been inside a pussy on one hand, and well into middle age, I had evolved into a sissy because it had been my only means to any kind of sexual gratification at all.

Buying and wearing panties, watching multitudes of porn, fantasizing and masturbating all but non-stop - that had pretty much been my sex life for years. But over the course of little more than a week, so much had happened that I couldn't even comprehend it.

First, I had basically been blackmailed and all but sexually assaulted by my boss, Katherine, and her sexy young niece, Monica. And then my hot, married neighbor, Misty, and her equally if not even hotter sorority sister, Megan, had given me a day and night I will never forget.

The most eventful day of my life had begun early this morning when Misty and Megan showed up unannounced at my door. To get things started, they had encouraged and allowed me to masturbate and cum on Megan's tits, as well as lick my jizz off her gorgeous globes. And then, after Megan had left to go get fucked by another man, she had returned to feed me her cream pie. And to top it all off, Misty and her incredibly well-endowed husband, Tony, soon arrived and allowed me to watch them fuck on my couch!

Of course, before that occurred, I had licked Tony's gargantuan cock and balls, "to get him ready for Misty." And while he had pounded her, I had jerked off, shot my load on the floor and licked it up, at Megan's direction. Finally, I had "cleaned up" both Tony and Misty, licking his cock yet again before eating her unbelievable bald pussy - and his cum with it!

And now, they were gone, leaving me in a crumpled heap in my living room. Megan, quite possibly the sexiest woman I had ever met, had offered to marry me - only as her way of establishing permanent residency in the United States. A Canadian citizen, Megan had made it clear that because of my "ridiculously small penis," she and I would never fuck. Rather, she would get all the cock she wanted elsewhere, and I would be her cuckold bitch - servicing her, and her male friends, whenever she and they wanted.

The benefits for me would include being able to quit my job and get away from my domineering boss, Katherine, and her threats to fire me if I didn't basically serve as her sex slave - and not in a good way! Katherine had kept me locked in chastity for the better part of a week and humiliated me to no end in front of nearly a dozen other women.

Remaining employed would mean being imprisoned in a cock cage nearly all the time, I was certain, and rarely being permitted to masturbate. If I married Megan, she said, she would take care of me financially as long as I served as her little "housewife," as well as her cuckold, jerk me off on occasion and maybe once in a great while, even give me a blowjob!

But now, Megan had gone off to "spend the night with Jamaal," the man who had fucked her earlier today, and whose cum I had eaten from her neatly trimmed, brown-haired pussy. Jamaal? I wracked my brain trying to figure out if I had ever known, or known of, a Jamaal who was not black. For the life of me, I couldn't think of a single one. Almost certainly, at this very moment, Megan was again enjoying a big, black cock, either sucking it or taking it deep up her cunt. And I had almost certainly swallowed a black man's cum earlier today.

As I crawled into bed, I knew that if I were to take Megan up on her offer, it was only a matter of time before I would be on my knees before Jamaal's, or another black man's, big cock. Rather than turning me off in any way, shape or form, the prospect excited the hell out of me. I had watched plenty of BBC porn, and I was well aware of all the stereotypes. Plus, there was no way any black man, or any man period, could have a cock bigger than Tony's. That was just not physically possible.

Lying in bed, naked, my little sissy clit began to harden. Even though I had cum this morning and again tonight, as well as the previous night in front of Katherine and her collection of power-crazed female friends, I was horny once again. Playing with myself, and utilizing the lotion that I always kept within reach on my side table, all I could think about was Megan and big, black cock.

Was I really prepared to make this incredible lifestyle change, to give up a job that I had been damn good at for more than 20 years and spend my time placating Megan and her assortment of stallions? God, she was so fucking sexy. Her tits were absolutely to die for, and it wasn't like I had any hope of getting sex, any kind of sex, anywhere else - except for whatever humiliation that Katherine and her niece, Monica, would dish out.

Continuing to stroke myself as visions of Megan - her face, her tits, her pussy and her ass - flooded my consciousness, I was extremely close to making my little clitty explode. Knowing that Megan had told me that I "would always lick up all of my cum, as any sissy should," I quickly retrieved a small glass from my nightstand, raised up onto me knees and proceeded to shoot my spunk into the glass.

Cumming for a fourth time in little more than 24 hours, there wasn't a ton of juice, but it still felt awfully good as I imagined Megan watching me jerk off. A bit hesitant to consume my ejaculate, as I pretty much always had been immediately after finishing, I nonetheless raised the glass to my slutty lips and drank down the nasty fluid, feeling proud because I knew that's what Megan would have wanted - and expected.

Absolutely exhausted, I had no energy to even get up and wash my hands or my face. Rather, I just curled up in bed, with the pungent aftertaste of cum overwhelming my senses. I felt like such a fucking whore - which was exactly the way I wanted to feel. I wondered if I was becoming addicted to cum - mine and other men's - as I drifted off to sleep.

Drained, in more ways than one, I slept soundly, until nearly 10 the next morning. The first thing that struck me upon awakening was the fact that my mouth still tasted like jizz. The second thing that struck me was to wonder how long I would have to wait to see Megan again. She had told me last night that we would get together in the evening to "discuss my options."

Megan had not applied any pressure for me to reach a decision, but it seemed clear she wanted one tonight. After all, she had said my options were "whether I wanted to go back to work Monday morning, or if I wanted to be her little cuckold bitch for the rest of my life."

What in the hell was I going to do? Could I, in a span of about 36 hours, receive a proposal from a woman I had only met the night before and make a decision to marry her, as well as quit my job? And, on top of that, agree to marry a woman who would never allow me to fuck her but would be fucking to her heart's, and her pussy's, content everywhere else?

I didn't even really know this woman. Could I trust her? Would she really take care of me financially? Would she really follow through with her sexual promises - to jerk me off now and then, and maybe even suck my little cock at least once in a great while?

Would I really be allowed to sample her pussy with my slutty tongue on a regular basis? And if so, how often would I be eating a cunt filled with another man's cum? And how often would I be sucking dick? Would it be too often? Not often enough?

Megan had told me I would have an opportunity to ask questions. I had plenty.

Needless to say, the day dragged. I tried to watch football on television, but just couldn't concentrate. I kept seeing Megan - and big, black cock - in my mind. And I didn't know when to expect Megan. All she had said was "evening." And I wasn't even sure if I should be dressed, but I was - in cute little bikini panties, gym shorts and a T-shirt. I mean, I couldn't stay naked forever, could I?

Finally, I received a text, from Megan, saying that she would be over about 6. Wait, how did she even have my cell number? Could she have gotten it from Misty? I didn't even think Misty had it. But there is the tenant directory put out by the apartment complex. Maybe Misty got it there, and gave it to Megan? I honestly had no idea.

Megan's text instructed me to dress in the sluttiest little outfit I could find - if I was still potentially interested in being her bitch!

Without a whole lot of options, other than panties, I remembered the bra-and-panty sets that Katherine had had me pick up at Victoria's Secret. I had worn the pink one for Katherine's "girls-night" party on Friday, when I was emasculated beyond belief - spanked unmercifully, strap-on fucked by multiple women, made to lick Katherine's asshole and forced to suck a real cock for the first time in my life.

I still had the turquoise and black bra-and-panty sets. I didn't like the turquoise, but the black was certainly appealing. I also had a pair of black, fishnet stockings that I had picked up on my own some time back. Those would go well together, I thought. About all I had otherwise to add to a slutty look was some bright red lipstick that I had played around with on occasion. Dressed in the stockings, bra and panties, and standing in front of the full-length mirror in my bedroom, I applied the lipstick as best I could. It didn't exactly match my fingernails, which were still adorned in pink polish - thanks to Katherine and Monica - but it was the best I could do. There was certainly no denying that I looked like a cheap whore.

So eager to see Megan, I was dressed and ready to go before 5. The ensuing hour-plus proved to be agonizing as I waited for Megan, and quite possibly, the defining moment in the rest of my life.

Finally, I heard the doorbell. My heartrate rising considerably, I moved quickly toward the door. Unfortunately, in my haste, I forgot to look through the peephole and when I opened the door, there stood a completely unfamiliar woman. She gasped as I appeared dressed only in a black bra and panties, and black fishnet stockings, with ruby-red lips and pink, painted fingernails.

Paralyzed by shock, I just stood there, as did the woman - a 30ish blonde dressed sharply in a medium-length blue skirt that revealed just enough of a sexy pair of legs and a white sweater that displayed fully covered but ample breasts.

"I ... I'm terribly sorry," I finally managed. "I ... I was expecting someone else."

Apparently realizing that I was harmless, that I wasn't going to pull her inside and assault her or anything like that, the woman smiled. She proceeded to explain that she was a campaign worker, pounding the pavement in support of a city-council candidate in the upcoming election. She handed me a leaflet and told me that she hoped she could count on my vote.

Why I didn't duck behind the door at some point during this exchange, I have no idea. Absolutely dumbstruck, I guess I was also taken by this woman's feminine charms. At any rate, I just stood there, my sissyhood clearly exposed. My little clitty stirred in my black panties as I apologized again.

"Have a nice evening," the woman said as she turned and walked away. I just stood there, watching her sexy ass, only to see her glance back over her shoulder and catch me staring.

Finally regaining some semblance of composure, I closed my front door just as the hot campaign worker disappeared from view. Jesus Christ, I thought, what I wouldn't give to fuck a woman like that.

Looking at the clock, I realized that it was still a few minutes before 6. Probably a good thing, I thought. I wouldn't have needed Megan witnessing that awkward moment.

I sat and crossed my legs like a good little slut as I continued to wait for Megan. I liked the way that made my little sissy clit feel. I really should have been born a woman, I thought. Had I been, I would have been the biggest whore and best little cocksucker ever known to man.

After a few minutes, the doorbell rang again. This time, I remembered to check the peephole. Indeed, it was Megan. As I opened the door, she eyed me up and down, told me that I looked nice and slutty, and entered my apartment. I closed the door behind us and watched Megan's ass as she walked to the sofa. Tight, purple pants accentuated her sexy butt, while a loose-fitting, multi-colored top pretty much hid the size of Megan's voluptuous breasts, but I certainly knew they were there!

As she sat down, I noticed that Megan had something in her hand. Upon closer inspection, I saw that it was a bottle of nail-polish remover, and Megan saw that I had seen it.

"Danni, if you decide to go to work tomorrow, you're going to need this," she said. "I'm sure you remember that Katherine told you to keep the polish on your toenails, but to remove your fingernail polish before going to work. And, of course, she told you to reapply the cock cage. I'm really hoping that neither of those is necessary."

Still standing, I felt the black bikini panties riding up my butt crack. Sometimes I wondered how women dealt with that, but then I figured that their panties probably fit better than mine.

"Danni, have a seat," Megan said. "I would guess that you are as anxious as I am to resolve this matter. I am still very much interested in marrying you - as long as you are prepared to live with the conditions I have set forth. I believe I have made my expectations perfectly clear and, honestly, I don't have a whole lot more to say right now. It's time for you to have your say, to ask any questions you might have, so we can try to work this out. That is, if you are still potentially interested - and judging by how you've dressed as a complete fucking whore, I would assume that you are still potentially interested.

"So what's on your mind, little Danni cunt?"

I didn't even know where to start. It seemed like there were a million questions I should ask, and yet they just weren't coming to mind.

"Megan, honestly, I think your offer is incredibly generous, and I am truly flattered. I mean, I know this marriage would be anything but the storybook, or usual, kind, but I am nonetheless honored that you would even consider marrying me. As I have told you, you are the most beautiful woman I have ever known. I just ... I just ..."

Megan rose from the couch and, just as she had yesterday morning, came and sat on the arm of the easy chair where I was sitting. She put her arm around me tenderly and bent down to kiss my forehead.

"What is it, Danni?" Megan asked.

Gathering all my courage, and knowing full well that what I was about to say could very well ruin everything, I nonetheless had to be honest.

"Megan," I began. "The truth is that we barely know each other. Please don't take this wrong, but the responsible side of me can't help but wonder whether I can truly believe everything you have told me. I mean, can I really count on you to take care of me financially? If I quit my job, I really don't think I will be able to get another one, and if you were to change your mind, or lose interest in me or something, I would be completely screwed. I'm really sorry. I just ..."

I couldn't help but start to cry as I told Megan this. It wasn't that I was saying no to her marriage proposal. I was just so confused.

"Danni, I understand," Megan said. "That makes perfect sense. But you might remember that I had mentioned a pre-nuptial agreement. That would be for both of our benefits. You would agree to live within the parameters that I set out, and I would agree to support you financially, as well as making sure that we meet all other concerns that either of us might have. Even though we wouldn't be husband and wife in the traditional sense, I would want both of us to enter into this marriage full of confidence and completely comfortable. Everything would be spelled out in a legal sense, but I promise you that you would never have to worry about money or anything of the kind. And I don't break promises, Danni.

"Look, I really do like you. It's just that, to be perfectly honest, I recognized a long time ago that I could never be tied down to just one man. I simply enjoy sucking and fucking different cocks too much for that. Usually, when I'm with a man, I don't even care about him in the least. It's just that I am absolutely addicted to cock. I don't know if you can understand that, but I hope you can. If it wasn't for those needs of mine, and if not for your, well, um, lack of size, you and I might even have a traditional marriage. But that's just not possible, under the circumstances. I do think we could be happy together, though, as long as you can handle my adventurous spirit. And I would like to see you get away from Katherine. I really don't think she is good for you."

I certainly felt better after hearing what Megan had to say, and I told her so.

"I guess the other thing on my mind, Megan, has to do with my, um, sexual gratification," I said. "You had said that you would give me a hand job from time to time, and maybe even a blowjob at times. Is there any way you could, uh, elaborate on that? I mean, in terms of frequency?

Megan laughed audibly.

"You are a horny little fuck, aren't you, Danni?" she said. "Well, look, I'm going to be straight with you. I'm not going to sell you some bill of goods and then pull it away from you after we're married. The truth is, I would say, probably nine times out of 10 that you cum, it will be from masturbating. Maybe even a little more than that. Ninety-five percent of my sexual energy will be spent with other men, and maybe even other women now and then. I mean, Misty and I do still like to fool around once in a while. And there might be others. But I'm not going to leave you high and dry, Danni. I promise that I'll jerk you off a couple of times a month or so, and yes, I'll even suck your little cock maybe once or twice a year.

"C'mon, I'll show you."

I couldn't believe it as Megan dropped to her knees in front of my chair and pulled the front of my panties down. Despite all the times I had cum that weekend, my pitiful penis responded immediately, and Megan took it in her left hand. She began to masturbate me with two fingers, one on the head and one on the shaft, and then she leaned down and began to lick the tip of my sissy clit!

I could not fucking believe it as Megan took the whole thing in her mouth. Of course, that would have been a piece of cake for any halfway experienced cocksucker, but my dick was in Megan's mouth! She slurped noisily as she tickled my little balls with her right hand. Megan looked up and made eye contact with me - just like I had seen so many women do so many times in porn movies! I was in absolute heaven as Megan sped up her pace, and in no time I was ready to blow.

"I'm going to cum, Megan! I'm going to fucking cum!" I said.

Just before my little dick exploded, Megan withdrew her mouth and proceeded to catch my cum in her right hand while jerking with her left. I nearly blacked out as I saw this incredibly sexy scene play out in my lap. As soon as I stopped spurting, Megan raised her right hand to my mouth, feeding me most of the cum while smearing the rest all over my face.

"I don't swallow, Danni," Megan said. "In fact, you will never, ever cum in my mouth. Is that clear?"

"Yes, Megan," I said softly, feeling a strong afterglow from my orgasm.

Megan walked to the kitchen and washed her hands in the sink. She returned and sat on the couch across from me as I remained slumped in the chair, my panties still pulled down and my little cock now completely limp.

danni5858
danni5858
144 Followers
12