As I explained in my first story (My first submissive), I’m fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn’t react well if they learned they had an amateur dominatrix on their senior staff.
Accordingly, before going much farther with my little hobby, I decided I needed to take steps to protect myself. I needed something resembling a slave contract.
Normally when there are references to slave contracts it’s a one sided document which specifies all of the things that the ‘slave’ must do and stipulates a litany of possible punishments resulting from failure. This wasn’t exactly what I had in mind.
The contract I needed would have some features of that, but was designed more like a commercial services contract between two consenting parties. That is to say, as ‘mistress’ the document explains my requirements and what I expect to receive from the contractee and also specifies what I will and won’t provide to the ‘subject.’
For example I’ve stipulated that I won’t inflict other than incidental pain, I won’t allow intercourse and have specified that sexual release will be at my option subject to specified circumstances. The other side of the contract specifies what my subject will do and not do. They will be respectful, discrete and substance free (among many other things).
Since discretion is of the utmost importance to me, the contract also specifies very real penalties that will occur if the contract is broken. These aren’t sexual penalties such as spankings or orgasm denials — they are real world and expensive. This document isn’t a game.
While the contract was generally written in my favor, it unquestionably provided both parties with protections against misuse. I’m not out to cheat or harm others and wish to avoid the same — this document helps enforce that.
Not very glamorous, I know. But let’s face it, I enjoy control. I’m not particularly into bondage, but a binding legal document provides me a certain type of control that dovetails nicely with the emotional and psychological domination that I enjoy.
As it happens I have a very dear friend; we’ll call him Jeremy, who happens to be an excellent and very accomplished lawyer. I knew he’d be the perfect person to put together my little agreement.
If Jeremy wasn’t a lawyer, he could probably have made it as a male fashion model. He is boyishly handsome, a very sharp dresser, extremely intelligent and quite wealthy both from his own earnings and family money. Unfortunately for the ladies, while he meets the definition of being bisexual, he identifies primarily as gay.
A number of years ago we dated for awhile and I can say he’s also a thoughtful and gentle lover. Back then he was just discovering a fondness for men and part of the reason we parted was his uncertainty about his sexuality. Though our relationship failed as a couple, it thrived as friends. We’ve both gained a confidante and have been keepers of each others secrets ever since (he’s only ‘out’ to a few people he trusts).
One night I met Jeremy for drinks at a quiet place we both enjoy. I explained about the development of my little ‘hobby’ and what I thought I needed before moving forward with in person scenes with my subjects. He was quite intrigued.
“I can’t say I’m entirely surprised. You always liked to take charge when we were together and I’ve never met anyone better than you at getting her way and playing mental games.”
“I’ll take that as a compliment I suppose. So you’ll do it then?”
“Yes, my dear “Mistress”, of course I’ll do it for you,” he said with a laugh. “It’s frankly an interesting legal challenge, and one I’m quite keen to try. Its no small feat to design a contract that falls somewhere on the spectrum between being a slave contract and a personal services contract but still manages to be a binding contract between consenting parties.”
“I don’t expect you to do it for free. I know this will take some time.”
“Please. I’m not going to charge you if that’s what you’re thinking. As I said, I like the challenge. But if you like my work, I’ll insist on you buying me a fantastic dinner and maybe …..I don’t know….”
“And what? You were going to ask for something else. What is it? You know I’ll do it.”
“….I shouldn’t, but….well…I want you to, you know, do a session with me.”
“Jeremy! Really? I didn’t know you’d be into that. Besides, I thought you were done with women? Have I turned you?”
“Let’s call it – once more for old times sake. I had some fantasies like this back when we dated and before, but I was so mixed up then and I didn’t think you were like that, so I never brought it up. Let’s let this be a chance to play ‘what if’ and then no matter what, we’ll both go on as though it never happened. Agreed?”
“I can think of nothing better. Agreed with enthusiasm.” With a laugh we shook hands on it as though it was a pact to end war in our time. We returned to our drinks and shared a relaxing evening with promises to get back together soon.
It was almost a month later when he called to say he had finished my little assignment. I reviewed it and then we talked about it one evening over dessert.
“It’s perfect Jeremy, and now there’s the little matter of payment. Do you still want the terms we talked about before?”
“Yes” and then weakly, “Ma’am.”
A few days later I called him and specified the time and place of our meeting. It was one of the city’s finest restaurants and I had pulled some strings to reserve one of the very best tables.
“I’ve arranged a driver to pick you up at your place at 7. We’ll have drinks and then we’re to be seated at 8:30. I’ll take you back to your place afterwards. I want you to wear that plaid blazer I always liked with a dark turtleneck and slacks ok? No suit and tie.”
“You’re the boss. I’ll follow your lead.”
“You’re darn right you will. Get ready for a very special evening my friend.”
It had been awhile since we had dated, but I figured a lot of his turn-ons would still be the same and I figured to play on several of them. Having a car pick him up, specifying his outfit and driving him home was all designed to restrict his control. To further set the scene for what I had in mind I chose my outfit very deliberately.
I wore a dark charcoal grey business suit that, apart from the buttons being on the wrong side, could have come from any men’s store in town. The pants were pleated and cuffed and I bought a red pocket square for the jacket. I also wore a French blue button front blouse that was again, a match a men’s work shirt save for the buttons.
Though the exterior said “male,” underneath was all female. I wore black satin panties, garter and sheer black stockings with my 4″ black pumps. To de-emphasize my breasts I wore a strapless bra that I cinched a little tight. I pulled my hair back to a tight bun and did my face with a bright red lipstick and deep smoky eyes.
The intensely feminine face actually served to highlight the contrasting androgyny of the outfit. It was a very erotic look that was right on point with Jeremy’s own sexual androgyny.
With a generous tip I had arranged for Jeremy to be seated in a cozy booth well away from the bar. I purposely arrived a little late as I wanted to watch his expression when I entered. The jaw drop was a bit wider than expected and his fumbled greeting was one of the few times I had known him to be at a loss for words.
After our drink order and a little small talk, I started right in with the teasing. Reaching across to pat his leg I said, “So it looks like you approve of my outfit. Are you ready for a memorable night.”
“Yes Ma’am” he replied with a grin.
In a very serious voice I said, “Just to be clear, I’m in charge tonight and even though we’ve been friends for ages, you’ll get the same treatment as any recipient of that contract you worked so hard on. Nod your head if you understand me.”
I didn’t exactly scare him, but he caught my tone and meeting my eye, he nodded.
In response, I removed a small gift wrapped package from my purse and slid it over to him. “Good. To get you into the right mind frame, take this package to the men’s room, find a stall and follow the instructions.”
With another small nod, he left to do as he was told. The package contained a training bra, a pair of bikini brief panties and a length of pink ribbon. His instructions were to put on the bra and panties and tie the ribbon around his cock and balls. He would be required to give me his ‘present’ when asked. The note also advised him that he was only to refer to me as Ma’am or mistress the rest of the evening.
As he returned to the table his red face showed me he had complied with my instructions. His nervous glances showed me he was worried about the bra showing through his turtleneck shirt. I could tell right off I had knocked him off balance a bit and he was starting to wonder what he had let himself in for.
“Don’t worry sweetie, no one knows your secret. It’s well hidden by your jacket. Do you want me to open my present here at the table or should I wait for later?”
“I think later will be better Ma’am,” he said and took a big sip of his drink. “You don’t play around.”
In a teasing voice I replied, “Of course not, besides it looks like you’ve gotten me quite a large present and I’m sure I’ll want to squeal and moan when I open it. Maybe you can make sure it doesn’t shrink for me over the course of the evening. Anytime I reach over there I want this to be hard ok?”
While he was away I had discretely taken a small dildo out of my purse and slid it down the inside of my thigh into the top of my stockings. Taking his hand in mine, I guided him to ‘my shaft’ and said, “Even though you’re my girl tonight, I want you to be just as hard as I am all evening ok?”
For the second time that night I saw my normally polished and composed friend go slack jawed and begin to stutter.
The teasing and role reversal continued over dinner. We were seated side by side and I took plenty of opportunities to tease him physically, mentally and verbally. Dozens of times I slid a hand over and grasped his pantied cock or stroked my fingers up his thighs.
On several occasions I leaned over and whispered, “I’m going to make you beg me for it tonight” and then bit his earlobe for effect. Another time I licked his neck and said in my flirtiest voice, “You realize you might not get to cum tonight, but I will. Several times.”
Outwardly we’d have looked like most any other smitten couple on a Saturday night. Some might have noticed Jeremy blush when I’d ask him how he was enjoying his bra or whether he wanted to borrow a lipstick or any of the other times I either taunted his masculinity or praised his feminine characteristics.
The food was delicious and we lingered over coffee to regain some energy for the evening still ahead. The sexual energy and tension was already quite high. After the waitress dropped our bill I slipped Jeremy a small bag and said, “Go put this on and then meet me out front.”
The bag contained very frilly, lacy ankle socks that would no doubt show just a little bit below the hem of his trousers and above the top of his shoes. I purposely took my time settling-up, which forced him to pace nervously around the front of the restaurant hoping no one would notice his feminine footwear.
When I finally emerged I didn’t give him a chance to speak, “Follow me to the car my dear, and please try to keep a couple of paces behind me.”
My car was parked a block and a half away and I smiled the whole way there. The whole evening so far and the prospect of what was to come had me aroused and I could feel the moisture seeping into my panties as I walked.
Apart from a little more verbal teasing, the drive to his place was uneventful. Once we got there I ordered him to “head to your bed room, strip down to your girly clothes and stand at the foot of your bed, slightly bent over with your hands on the foot board.”
Giving him a minute or two get himself together, I came up behind him and quickly used a couple of old neckties from his closet to tie his hands to the footboard. I then secured a blindfold over his eyes.
The sight of him standing there in bra, panties and frilly ankle socks tied to the bed and completely vulnerable was delicious and I couldn’t resist rubbing myself as I watched him nervously shift in front of me. He had no idea what was next, but had gamely followed my lead so far and that submission was quite arousing.
“Yes Ma’am, no Ma’am and thank you Ma’am are all I want to hear from you understood? Stay there. I’m going to get myself ready.”
Leaving him I headed for his bathroom where I took off my pants and slipped on a harness and a six inch strap-on cock. I didn’t really have any experience with a strap-on, but wasn’t sure that would matter for what I had planned. This particular model had a reservoir into which I loaded a vial of theatrical ‘cum’ that I had made using a recipe I had found on line (a surprisingly easy thing to find).
I put my pants back on and positioned my ‘cock’ so it stuck out the front zipper. I then went back to the bedroom and lay down on the bed in front of him so my cock was right underneath his head. I then propped my head up with a couple of pillows so I could watch the action.
“So my little slut, I can tell you’ve been thinking about my cock all night. I bet you want to suck it don’t you.”
“Its right in front of you why don’t you lean down and get started. I’m sure an experienced cock sucker like you can take the whole thing no problem.”
“Yes Ma’am, thank you ma’am.”
He leaned forward and tentatively found the top and then gradually slid his mouth over the hard plastic phallus.
“Wait a minute. A cock sucking slut like you needs some lipstick. Let me help you”
“Ummm Yes Ma’am”
I quickly applied a slash of lipstick to his lips making him look all the more girly.
“Now those are some good cocksucking lips
A few seconds later he began to bob his head up and down a bit so I figured I’d give him some encouragement. As he did this I slipped a hand down my pants to finger my clit and was rubbing my breasts through my shirt.
“Ohhh yes sissy. That feels so good. You’re such a good cock sucker. Get into it sweetie. Let me see your pantied ass shake as you go up and down on my pole.”
“Ohh more. Take it all sweetie. Show how much you want it. That’s a good girl. Take it all into your pretty mouth. Such a sweet innocent girl sucking a big hard cock.”
I continued like that for a few more minutes and as my own orgasm approached said, “Yesss, oh yess, right there, ohh yes I’m going to cum sissy. Take it bitch, suck me hard and make me cum.”
With that I reached down and squeezed the attachment that made the ‘cum’ shoot from the reservoir into his mouth. He flinched at first in surprise, but then tried to stay on top of it. After another blast I deliberately pulled it away to shoot another two jets onto his cheek and chin. I came myself as I watched my ‘cum’ dribble from his mouth.
Removing his blindfold I told him, “Look at you with cum all over your face. What a slutty little girl you are. Don’t you know good girls swallow their men? Are you sorry for being such a poor excuse for a sissy?”
“Yes Ma’am. Sorry Ma’am.”
“Sorry is right. I should bend you over my knee for a spanking but you’d enjoy it too much. Your little sissy stick looks very hard. I think a good hard fucking is what you need. Do you want that? Do you want to be fucked hard like a pretty little sissy slut?”
“Yes Ma’am please. I’m so hard”
“Quiet. I don’t think you’ve earned the right to fucked by my cock. I bet a sissy like you has a cock she likes to play with don’t you? You have your own dildo don’t you sissy?”
Sheepishly, “Yes ma’am, I do”
“I’ll untie you then. Go get it, lube it up and put in. Then I want you spread eagled in the middle of the bed. Get going. I know how bad you want it.”
I untied him and though he couldn’t bring himself to look me in the eye, he set about the task I set him. His cock stayed rock hard the entire time and I encouraged him with a few additional comments about how pretty he looked and how slutty he was. I even made him ask permission before letting him stick his dildo into his ass.
“Please Ma’am. Please may I stick a dildo in my ass?”
“Of course you can sweetie. I’m sure I couldn’t keep a slutty sissy like you from doing it anyway.”
It took him several minutes to work the cock into his ass and I’m sure it was made harder by the fact that his “master” and former girlfriend was watching him impale himself.
He was red faced the entire time and I’m sure felt more than a little shamed to be giving in to this particular need. While I knew he was bisexual, it was more a conceptual thing before now. This scene was making it very real and we both knew it.
Once he was in position, I straddled him and aimed my ‘cock’ at his face. “So is my little sissy ready to take big hard cocks in both ends? Kiss my cock and thank me.”
“Thank you Ma’am” he said with a kiss to the big fake head..
With that he began once again kissing and sucking on my strap-on as I gently fed it in and out of his mouth. I loved the power that I had over him and my clit was buzzing at the way he submitted to my commands.
I needed another orgasm myself and while I wanted to heighten the tension a little more, I had seen enough cocks to know that his wouldn’t last much longer. I let him build up a little energy and then reached back and began firmly stroking his cock inside his panties.
“You like that don’t you sissy. What a slut you are. A cock in both ends and still not satisfied.”
“You want to cum don’t you baby. You want to gush cum into your panties don’t you.”
“Nod your head and moan while I stroke you….”
“Beg for it now. Take the cock out of your mouth and beg”
“Please Ma’am. Please may I cum.”
“Whose sissy are you?”
“I’m your sissy Ma’am, please I’m close.”
“You’re not a man are you. You’re a sissy. My pretty little girl. Tell me what you are.”
“I’m your sissy.”
“I’M YOUR SISSY…..mmmm please.”
“Who is the real man here.”
“YOU ARE, You’re the real man. I’m a cock-sucking sissy….”
“You may cum”
With that he erupted with a huge groan, shooting several blasts into his panties and onto his legs and chest. I scooped up some of his cum and wiped it onto the head of my ‘cock’ then ordered him to suck it off while I quickly rubbed myself to another orgasm.
Rolling off him, we both lay there spent for several minutes before he leaned over and said, “That was incredible, you were incredible. The whole evening was amazing. How did you know I’d be into all that? I wish I had discovered this side of you a long time ago.”
“We’ve been friends for a long time Jeremy, I’ve always known what you wanted, I just didn’t know I had it in me to give you. It was pretty good wasn’t it? I still haven’t unwrapped my present yet. Are you ready to give it to me now?”
We kissed a little then we cleaned up a bit before I removed the pink bow from his cock and we enjoyed a more conventional fuck session that lasted until the wee hours of the morning (although I was on top of course).
Over breakfast he asked, “I know it was just supposed to be once more for old times sake, but could I maybe see that side of you again some time?”
“I don’t know, you’ll have to sign my contract and I have a very good lawyer.”
“No worries then, the best lawyers also know all the loopholes.”
Although Jeremy remains more gay than straight, he and I have enjoyed a couple of other ‘sessions’ together and we remain the best of friends with benefits, of a sort. I get benefits whenever I ask for them, he only gets them with my permission.
I never did make him sign the contract.
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