Dressed Up For A Bi Surprise

This is a semi true story about me, but although up to the fateful day is mostly true, what happens next is still a fantasy, for now.

The story involves a guy being "forced" bi, even though it's something he wants deeply. It's complicated wanting something badly but not feeling able to ask for it yet not being in control is key to the fantasy.

Constructive comments welcome.

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Something was different from before. The spanking was suddenly harder and more intense. Strong hands gripped my suspender belt pulling me back towards something hard, but this time it wasn't the cold solidity of a strapon, this was warm and somehow organic. As what could only be a hard penis entered my virgin ass I knew that even though I was tied wrists and ankles to the bed I should try to resist but as my mistresses voice whispered in my ear "take that cock my little slut", I pushed back....

.....

Today had been decades in the making. On the surface I'm a normal guy, decent job, happy family etc etc, but that is only 99% of me, the other 1% is kinky and deviant.

I've had a few girlfriends/lovers over the years who have been happy to indulge my love of women in stockings and enjoyed me tying them up, blindfolding them and spanking them. It's always ended up more complicated though and at least one side ends up emotionally attached so about 15 years ago I went to visit an escort called Mags.

Her bio floated my boat with lots of pictures of her in a variety of outfits, all with stockings and suspenders. The written part described her as simply unshockable with a huge menu of kinky desires.

The first few visits were an eye opener. After meeting me at the door dressed to impress it was straight to bed for intense sex. On the very first visit I learned something new. As she sucked my cock she pushed my legs back and to the side before sticking a finger up my ass. As she used first one then two fingers on me I had the biggest orgasm of my life, shooting a huge load into her waiting mouth.

On the second visit she did the same but this time worked up my body held my wrists down and kissed me, my cum dripping into my shocked mouth.

I continued visiting every 6 months or so when my horniness would overcome my fear of getting in too deep and every time something new would be added to our repertoire of kink.

First up it was strapon fun on me before "normal" sex which became kinkier and kinkier as she used bigger toys on me and took me in all sorts of positions.

Then it was me being blindfolded and spanked, first with her hand and then a selection of paddles and whips.

Although I enjoy being dominant in bed, this new found submissive side was really starting to turn me on and I looked forward to dirtier and kinkier experiences on each visit.

Mags had noted early on that I love a woman in stockings and suspenders and how my hands would gravitate to stroking her thighs, squeezing her ass with my hands underneath the garter straps or pulling on the belt as I fucked her hard from behind.

One day as we lay on the bed working up to some fun and I was rubbing my legs against hers and pulling her suspenders, she asked me outright what I liked about them. I wasn't, and still am not, sure why I love them so much but I told her I get off on the feeling of stockinged legs rubbing against mine. With a wicked glint in her eye, she went to her dresser and brought out another pair of stockings. I couldn't quite believe what was happening as she rolled first one, then the other up my legs. Part of my brain was in open rebellion but the other part that controlled my cock had other ideas and I was hard as a rock as she cuddled up to me and our legs rubbed against each other. The feeling was indescribable and although I felt a bit silly, soon I was fucking her as she wrapped her legs round me and stroked them up and down my thighs.

Over the next few visits, I'd turn up and she'd be waiting with stockings and suspenders for me to wear. She was becoming more dominant as well, blindfolding me, spanking me and fucking me with her strapon before feeding me my cum.

She is truly a master of her craft as if this had happened on day 1 I'd have run away and never come back, but the slow drip feed of escalation had me ready to be "her little slut, little bitch" as she liked to call me.

After many years I had my own lingerie, a dress and high heels. I'd wear the stockings and suspenders on the way to see her which felt terrifying in case somebody noticed but the command of "strip and show me what you've got on slut" was (and is) a thrill worth the risk. Nearing 50 I'm in no way passable as a woman but I'm in decent shape and have shapely, if slightly hairy, legs. The look of condescending amusement as she adjusts my stocking tops or garter straps is a huge part of the turn on for me.

One day I was tied face down, ass up, wearing stockings, suspenders, a corset, high heels and bright red lipstick. I was blindfolded as she drove her strapon into me from behind, spanking me and telling me to push back on her hard cock like a little bitch when she ramped it up once again.

"I bet you'd like a big cock to suck on, wouldn't you" she asked. I'd honestly never considered it but she flogged me and told me to tell her how a sissy like me would suck a cock while she pegged me.

I told her please don't make me do that and she was not happy to say the least.

"You'll do whatever I fucking tell you to you sissy bitch. If I tell you to suck a cock, you'll suck a cock. If I tell you to take it up your dirty, slutty ass. You'll take it hard and enjoy it. If I tell you to dress up and fuck another sissy slave YOU'LL...... FUCKING......DO......IT......". With each word she rammed me to the hilt and spanked me as hard as she could and I erupted for what felt like forever. I thought it would stop there but she kept hammering away at me her slaps ringing out as my cheeks throbbed. I was ashamed and wanted to stop but she was relentless.

Then she started whispering in my ear again, "Seems like you want a big, fat cock to suck and fuck".

"Please no" I moaned.

"I don't care what you want," she growled, "if you come here again I'm going to make you be a little bitch for another slave, you'll suck cock until your lipstick is all over it then you'll beg him to fuck you like the little sissy slut that you are".

Again I moaned "please no" but my body betrayed me as my cock had returned to life. She untied me and I wrestled her onto her back. Pinning her down I quickly rolled on a condom and buried my cock in her wet cunt. I fucked her like an animal as she lay there whispering "fuck my little wet cunt, sissy slut, you're my little cocksucker from now on, imagine what a big, hard cock will feel like in your ass as you beg him to fuck you harder". I maybe lasted 30 seconds before yet another powerful orgasm ripped through me.

What I like most about Mags is after ramping up to a level of kinky intensity that's sometimes unbelievable, she can just as quickly switch to normality and have a chat. As we lay recovering she asked if I'd like to do the things she'd said. I was open and told her that if left to my own devices, I'd not even touch a guy beyond a handshake, but I really get off on her telling me what to do and if I felt like I was being forced into it, it was pretty obvious from what we'd just done and how I reacted to it that I'd go along with it.

So today I had the opportunity to visit again. I hadn't forgotten our fun from the time before and was sure we'd do something similar again but was also sure that this was just a mental game we were playing.

So as usual I turned up with stockings and suspenders under my jeans and got buzzed into her flat. Usually she'd be in her stockings and heels, tell me to strip and ask what I want to do but today was different. She was dressed as a school teacher with high heels, black stockings, a tight black skirt, a white blouse, red lipstick, hair up in a bun and a cane in her hand.

Restraints were already on the 4 corners of the bed along with a selection of butt plugs and strapons, along with a short plaid skirt and another white blouse.

She sat on a chair, crossed her legs and coldly looked me up and down. A shiver went through me as she said "tonight you will call me Mistress. I am a teacher at this school so you will do everything I say, do you understand?"

"Yes Mistress" I replied.

"We have a problem at this school. Somebody has been stealing underwear from the laundry.... and I happen to think it is you. Well, is it?" she asked.

"No Mistress, why would I do that?" I replied.

"Because... YOU'RE.... A.... LITTLE....SISSY....SLUT" she shouted at me, punctuation each word with a slap of the cane against her other hand. "Now take off your fucking clothes..."

With trembling hands i took off my jumper and t shirt. My cheeks burned with shame as she stared at my torso, particularly at the lacy bra I had on.

"I thought so, now take the rest off." She commanded.

Trainers and socks, then jeans came down revealing my stockings and suspenders and a raging hard on.

"Now what is in your fucking bag?" she spat.

I emptied it out showing her high heels and bright red lipstick.

"Put them on... NOW" she yelled.

Once I'd done as I was told she stood up and walked round me slowly, stopping behind me. I felt her hands adjusting my stockings and bra. I went to touch my raging hardon and ohmyfuckinggod that hurt as she swatted my ass with her cane.

"Don't you dare touch yourself you piece of shit. We have something of a problem here. It seems I've caught a thief and you must be punished. However, this would look very...very...bad on the school, so I will give you a choice. I can either phone the Police with all the shame that will involve for you and the school, or I can phone the headmaster and together we will come up with an appropriate punishment. You have 1 minute to decide. If you decide to accept my punishment, put on the skirt and blouse and get face down on the bed, arms and legs out. I can see you're thinking that a spanking with this cane is a small price to pay to preserve your secret, but I warn you it will be a much harder punishment than you expect. Now choose."

Oh fuck, this is crazy I thought. With an inkling of where this was leading, every instinct was telling me to say stop and have a "normal" session, but my aching erection was telling me to do as I was told.

She sat back down and toyed with her phone as I picked up the blouse and buttoned it, then the plaid mini skirt that didn't come down as far as my stocking tops. I put on a thick coat of lipstick and got on the bed, face down.

"Wrong way, head towards the bottom of the bed. Head down, ass up!" she snapped and left another red line on my ass with her cane. I turned round and my wrists and ankles were quickly secured to the bed. Then a ball gag was placed in my mouth and a hood put over my head and eyes.

I was panicking a bit now and wanted to stop and tried to talk round the gag.

She continued "I know you don't think you want to be my little cocksucking slut, but you see, I really get off on having a strong, dominant man like you at my mercy. You're gagged, there is no safe word, I could take photos of you on your phone and send them and theres nothing you can do. I would say relax and enjoy this, but you won't be relaxing for a while and I dont give a damn if you enjoy it."

She got behind me and my skirt was lifted up and over my back, leaving my ass on display. I felt her familiar lubed fingers on, then in, my tight hole. She must have selected a large butt plug from her collection. It was bigger than I usually take and although the first bit entered easily she really had to force the matter with the thick part, rotating it and shoving it hard. With the final encouragement of a few hard slaps to my ass it slipped in and was sucked in to the base.

I was breathing deeply, trying to get used to it when I felt Mags get off the bed. I wasn't sure what she was up to until I heard the sound of a ring tone through her phone and a male voice answer with a curt "hello".

"I have him tied up and I'm about to start his punishment, I think you should come round and help. Wear what I told you to and don't take too long" and she hung up without waiting for a reply.

To me she said "The headmaster is on his way. In his own way he's nearly as much of a sissy as you but you will be bottom of the food chain today. So let's get started. Ass in the air bitch!"

I stuck my ass out as much as I could, the large plug still making itself very known pressing on my prostate. I was full of confusion, the overwhelming horniness of this level of kinky depravity offset with nervousness about what would happen when the "headmaster" arrived. I guess I still thought this was just a game. I was wrong...

SMACK

I screamed into the the gag as what felt like a leather paddle swatted my left ass cheek hard.

SMACK

I pulled with all my might on the restraints as she swatted my right cheek.

SMACK, SMACK. SMACK. SMACK, SMACK...

She began a relentless assault on my ass cheeks and upper thighs as I moaned into the gag and she teased me "not long until you get to suck a cock slut. That big plug in your arse is stretching you out, maybe I'll make him fuck you. Maybe you'll even beg for it."

And on and on for what felt like an eternity but in reality was no more than 5 minutes. As it went on and my cheeks were already on fire, I wasnt exactly enjoying it but my cock started to rise and at the same time I started to push my ass back for the next spank, which had the added benefit of making my garter straps tighten and pull on my stockings.

When she stopped she slowly pulled the plug out leaving the thick part stretching my hole as I groaned in a mix of pain and pleasure before it finally popped free. It felt like I was gaping as she pushed a few fingers in and out applying more lube.

"Now its time for your arse to take my cock. This is the strapon you managed to take before but begged me to stop as it was too big. But you're nice and loosened up and you can't beg me to stop this time anyway." She teased.

Now I was really worried. It had hurt so much feeling like my ring was going to burst, an indescribable feeling of fullness and the tip nudging up against something deep inside that was on the uncomfortable side of sensations when she gave me a few gentle strokes the last time and it had never made a return in our sessions.

I wasnt given much time to contemplate though as her fingers left my hole and I felt her stockinged thighs rub up against mine as she positioned herself behind me. I felt the big plastic end of what I knew was a lifelike cock with a big head and veins and without any ceremony it started a fast and relentless journey into my bowels. I never knew she had so much strength in her hips as she drove it balls deep in 4 or 5 thrusts even as my ass desperately tried to repel the invasion. I think my mind took a short wander at that point and I nearly blacked out but I was brought back to life as she pulled me back by the hips. "Push back slut, fuck yourself on my cock. Be my dirty little whore". Instead I tried to pull away from her but all that achieved was she was now lying on my back allowing her to use her weight to drive that thick dido deep.

My cock had shrunk again as it felt like the fake cock had taken over all my senses. Despite the pain as she went to town on me, fucking me hard, I was getting off on the feeling of our stockings rubbing together and, knowing how to tease me, she gripped my suspender belt pushing it up my back, making everything tight.

I was wondering how this was going to end when the door buzzer went. Oh no, maybe this is real I thought. Mags gave a sigh as she pulled out of me pulled my skirt back down and with a laughing "don't go anywhere" I felt her get off the bed and the door lock buzzing open. She opened the front door a crack and I heard unmistakably male steps coming up the stairs, into the flat and the door closing. Not a word was said but I could feel that more than one person was present and the unmistakable sound of someone undressing. My cheeks burned in shame knowing that another guy was seeing me in this very vulnerable position. Dressed in stockings and suspenders, high heels and a schoolgirl outfit.

I wasn't left much time to think as my skirt was once again pulled up and another dildo started to press at my tender ass. Fortunately Mags had swapped for a slightly smaller version and I felt the familiar hardness and coolness of a (this time) smooth dildo glide easily inside me. She pushed me down onto my stomach and whispered in my ear "I'm going to take your gag out now. If you make a noise I don't like or don't follow my commands, I'm going to kick you out in the street dressed like this without your car keys, do you understand?"

I nodded and the strap was unbuckled and the ball popped free. My jaw ached a bit but it was told to stay still as a thick layer of new lipstick was applied. "Open your mouth and stick out your tongue" she instructed. I did as I was told. I smelled a faint muskiness mixed with shower gel and could almost sense a cock in front of me. My heart was hammering in my chest as I felt warm hard flesh rub over my lips and outstretched tongue. All of a sudden I REALLY didnt want to do this anymore but I had nowhere to go so thought if I sucked him off quickly this would all be over.

Mags was making excited noises as she started fucking me again whispering in my ear to lick that fucking cock and other perverted endearments. I did as I was told and ran my tongue up and down that shaft and around the head, trying hard to get it in my mouth so it could be over but he'd pull back as I was held by my restraints. Eventually he took my face in his hands and pushed his thick cock past my lips and into my mouth for the first time. "Now SUCK bitch!"

I sealed my lips round the mushroom head and ran my tongue round and round it, doing all the things I like having done to me, like flicking a tongue on the underside of the glans. It wasn't unpleasant and as he started to slowly push in and out, getting quicker as Mags whispered what a good little slut I was my cock had returned to life. As his thrusts became more urgent I thought that this would be over soon and was starting to wonder if he was going to cum in my mouth.

Mags understood what i was trying to do and spoke directly to the guy, "I think you should fuck this dirty slut's tight ass, we can't have a thief in the school. Can we? There needs to be consequences to make sure he doesn't do it again. Do you want to fuck him? I think some pictures of him dressed up with your cock in his ass will stop him misbehaving."

"Let's see if he wants it shall we" the man finally spoke as he withdrew from my mouth, slapping his hard cock against my cheeks and lips a few times. Mags gave me a few hard and deep thrusts with the dildo to get my attention.

"Please don't. I'm so embarrassed and ashamed. Please untie me and let me go". I begged.

"Do you think you've got a choice?" Mags sneered in my ear slipping the ball gag over my head and into my mouth once again. She pulled out and I felt the weight change on the bed behind me.

Once again I felt the familiar sensation of stockinged legs rubbing against mine and a hand spanking my ass, but...

Something was different from before. The spanking was suddenly harder and more intense. Strong hands gripped my suspender belt pulling me back towards something hard, but this time it wasn't the cold solidity of a strapon, this was warm and somehow organic. As what could only be a hard penis entered my virgin ass I knew that even though I was tied wrists and ankles to the bed I should try to resist but as my mistresses voice whispered in my ear "take that cock my little slut", I pushed back....