Femboy Bondage Pt. 01

Femboy Bondage part one

Any comments or feedback about this story is appreciated.

I'm a 23-year-old femboy living alone in a new state, I mainly dress up in private but have gone in public a few times, usually, I stay in and take photos of myself using my camera. I've been feminizing myself since an early age to the point where the few times I do go outside I'm mistaken as a girl. Not only do I love dressing up, I also love bondage. I've tied myself up a few times, but it's always been difficult and there are lots of positions I want to try but can't do it alone. I decided to look through a local subreddit, of course, most men are looking for real females, so I made my post and added a photo of myself dressed up, in makeup, heels, wig, and tied up with my face hidden.

23 [M4M] Femboy looking for bondage

Hello, just as the title states, I'm a femboy looking for bondage. I would prefer someone with experience that isn't just interested in sex. I'm open to pain, groping, teasing, edging, and gagging. Please be able to host and be at least 30 years old.

I post the ad and proceed with my night, it's Friday evening and ideally, I'd like to hear from someone tonight so we could meet up this weekend. I get a few replies, most asking for pics, others around my age but I made it clear the age I'd prefer. One person's message caught my eye.

Hello, I'm 37 with experience in bondage, I have lots of gear that I would love to use on you. I have no desire to have sex, however I will be groping you when you are tied up and other things we can discuss. While the outfit in your photo is cute, I'd like to see you dressed a little sluttier. I'd like to explore more options for what you will wear. Also, I will require you to wear chastity specifically one I will put on you. I can host this weekend if you are up for it.

Reading his message made my cock grow, I did own a chastity cage but the fact he wanted to put one on me made me instantly excited, I wasted no time messaging him back showing my eagerness. He responds quickly and we discuss what I wear deciding on my black pleated mini dress. I will wear the collar and black heels that go with it as well as a black thong. Our conversation shifts to the idea of me spending the night and wearing a more fun costume the next day. We agree on a me wearing Japanese navy sailor uniform with a garter belt, white thigh highs, and white thong. This was my favorite costume to wear, and he mentioned that chastity would go very well with both outfits.

We agreed that I would arrive at his home by 11:00 am, discuss some things, sign a contract, and then begin our bondage session. Everything about this felt very professional, we're both getting an equal amount out of this. I get things ready for the day ahead and hop into bed.

The next morning, I start getting ready, putting on the pleated mini dress, thong, and heels. I put my wig on, apply the right amount of makeup, and practice walking, talking, and behaving like a woman. Something he mentioned, was he wanted me to not just look passable but act like a woman as well. As I grab my bag and put it into my car I GPS the directions and off I go already so excited.

When I arrive at his home, it appears like a very normal house in a nice neighborhood putting me at ease. I remember he mentioned for me to quickly walk up to his front door and knock to avoid any suspension from the neighbors. That's exactly what I do, stepping out of the car when I see no one around, grabbing my bag, and trying my best to hurry to the door in heels. I knock on it and already hear footsteps approaching. The door opens and I'm met with a very normal-looking man, he gestures me inside and I quickly go in as he shuts the door behind me. Immediately he started to speak to me thanking me for cooperating with him, he didn't want his neighbors questioning why a woman dressed provocatively would be entering his home.

"Please I can take your bag and put it in the other room. In the meantime, the contract is on the table take it and sit wherever you like in the basement." He tells me, I hand off my bag thanking him. Walking over to the table I grab the contract, which is two sheets of paper, I make my way down the stairs and into the well-lit basement. I sit down on a chair and begin reading it over.

It outlines the toys he has, bondage gear, and photos of positions he can tie me in. While reading it over I look around and see some of these toys and gear around me. More notably a spanking bench, a padded restraint bench, and a St. Andrew's Cross. All of these have me instantly hard, I try to hide it continuing to read through and mark things as I please. He comes down the stairs sitting on the sofa by the table. "If you have any questions, please feel free to ask." I nod and continue reading and signing my name on things.

One thing that drew my eye in the contract was a mention of "forniphilia" and an image of a woman being used as a chair. Not aware of this I asked him, "What is forniphilia?" He smiles, "That is where you would be made into furniture like a chair, table, etc." I jot that one down as an interest and not a limit. Reaching the end of the contract I sign my name at the end it says,

"Please highlight which you would like to be called, "slave, slut, or boy." I highlight "boy" and "slave" thinking both were equally humiliating. Once you complete this contract get on your knees and say, "I'm ready ___ (sir, master, daddy. Pick which one you will call me for the duration of our session.) holding the contract.

I get down to my knees holding the contract out, "I'm ready Sir." I say to him. Sir gets up from the sofa and walks towards me taking the contract. He signs his name and puts it on the table. He sticks out his hand, and I grab it. He leads me over to the padded bondage bench instructing me to lay down on my back, I do so looking at all the straps attached to it. He walks away toward a glass case with different gags, I see him grab a ball gag as he walks toward me. "Open." He orders, and I obey opening my mouth. He sticks the gag inside, pulling my head up to strap it around. He lets go and plops my head back onto the padded bench.

He grabs one of the straps and pulls it over to the other side of my neck then strapping it. Next, he goes for the strap around my chest, stomach, and each hand. I feel him spreading my legs apart then pulling the pleated dress up a bit exposing my thighs and legs. He strokes them lightly and we both see my noticeable bulge. He laughs reaching at the ground and pulling up a spreader bar. He goes to each leg cuffing it in the bar and spreading my legs more and more till they slightly offset the bench. I start to shake a little in anticipation of what will come next as he stands there looking at me.

He steps closer and begins groping my legs, especially my thighs. He slaps them with his hand and smiles as I shake. He goes back to the glass cabinet and before I have time to process what's in his hand, I feel a sharp pain on my thighs. He just whipped them, I let out a grunt in pain, and he hit again this time a little harder. My body tense up anticipating another hit but this time it's multiple, back-to-back smacks on my thighs. I cry out but the gag limits me, still completely tensed up waiting for his next strike I look and see just how red I am down there.

He sets his whip down, "Good boy" as he strokes my thighs, they sting as he touches them but he slowly makes his way up to my cock, he touches it lightly. I feel him palming my balls before squeezing them. I jitter in pain as he does this, with his other hand he pulls up my pleated dress and pulls the thong away revealing my cock as he firmly holds my balls. He looks at me and I know he sees my look of worry as he smiles at me. His grip tightens until he lets up still looking at me. I assume it symbolizes he owns me at this moment. My cock is so hard at all of this, he lets go of my balls and starts stroking me. I beg him through the bag "Please" but it's all muffled, I want to cum so bad. He knows this though because the minute I start twitching slightly he stops and walks away from me.

A minute or two later he goes back to stroke it some more then stops right when I'm about to cum. He repeats this process ten times, my cock so red, and at attention. He laughs and strokes it one more time then stops and immediately grabs my balls and looks into my eyes. I can't take it anymore and let out my load. He still holds them in his hand showing his control over me. My cum gets on my dress, legs, thighs, and some of his hands. He takes cleans my cock with his other hand and puts the cum on my thighs, his other hand still holding my balls even as my erection shrivels away to almost nothing. "That's more like it." He says leaving and coming back holding a chastity cage, I feel like tinkering around pulling my balls through the ring then pushing the rest of the cage over my cock, I hear a click and see him holding a small key.

He places it by the cabinet and then returns me, to touch and grope me some more, he admires my caged cock for a bit then pulls my dress over it. I feel him loosening the spreader bar and then the rest of the straps. He pulls me off the bench and onto the nearby spanking bench where he lays me across it, my ass completely exposed. He straps me in starting with my legs, back, then arms, and hands. My head is free to look around but with limited mobility, I don't see him behind me as I feel him pulling my skirt back up to reveal my ass.

Suddenly I hear a loud bang and shriek in pain as he paddles me once very harshly. I try to turn to look at him but am limited, I see him winding up to make another swing. *SMACK* another hit on my ass, and I muffle in pain through the gag. I can't imagine how red I am, *SMACK* the third hit makes me cry, this doesn't feel like pain anymore, it's torture. I'm at the complete mercy of this man with whom I willingly signed a contract to be tied up and played with by him. I tense up in anticipation of another hit, I can feel him right behind me he hasn't left. The seconds go by and just when I think he's finished, *SMACK*

"mmmmmph Ahhhhhh!!!" even through the gag I scream in pain, I can't take this anymore, it's going too far. I hear him set down the paddle, his hand rubs my ass and I feel the stings of the hits. "Good boy, I promise that's the last time you'll feel pain like that with me. I need to see how much you can take. I've never had a slave take more than two hits before screaming like you just did." His statement eases me back, while he caresses the body. He pulls my dress back over my ass and walks over to my face, he pulls the ball gag out and it goes under my chin, and he speaks to me.

"Slave, we both agreed on no sex; however, you mentioned an interest in fucking machines, you are already in the proper position, would you like to try one on your ass? I have two that can take turns while one hole is free the other is filled. Are you interested?"

His offer makes me nervous, "I can't handle something like that right now, but I would be okay with just you using a dildo on my ass to start then in another session try the fucking machine." I reply to his question.

"That is perfectly understandable, just know I won't be taking it easy on you. Also, if you cum and I know you will expect to earn a plug in the ass for the remainder of our session. Are you okay with that?"

"Yes Sir."

He smiles and pulls the ball gag back into my mouth where it belongs. He leaves and I hear him return, my dress is pulled up, and the pain from his hits is still there and intensifies as I feel him inserting that dildo in my ass. It takes some work, as he slowly inserts it. I start to feel immense pleasure from this, my cock wants to get hard so bad. The dildo is about halfway in my ass until I feel him pull it out quickly, he then shoves it in with no regard. I jerk forward and let out a gasp, I feel it deeper inside me and let out a loud moan. Before I know it, I'm already cumming, my moans make it very obvious, and he pushes it in and out. I keep moaning from pleasure until I go limp. At this moment he's in disbelief, "Already?? No way." He chuckles and laughs pulling the dildo back out. Before I can even gather myself, I feel another toy make its way inside me.

"I didn't expect you to cum that quick, clearly you've been wanting that for quite some time." He laughs while tapping on the plug in my ass then gets up and returns to me so I can see him. "I'm a little tired of the basement slave, it's getting hot in here. I'll let you stay down here for a bit to recover while I get the upstairs ready." He goes back behind me then as he goes up the stairs, I see him bringing some rope with him. He makes a few trips up and down bringing different gear with him and a few breaks in between.

Time goes by and he returns over to me, taking off the restraints and grabbing my hand to lead me upstairs. The plug in my ass is a first causing me to not walk properly, he helps guide me up and in the living room, I see lots of rope laid out and a new outfit. "I suggest you change into this new outfit I have for you; I think it will be more comfortable than your current one." On the ground is a black sleeveless bodysuit along with black thigh highs, and black gloves. I begin undressing and once I grab the thigh highs, I notice they get stuck together, I realize it's all latex. I get excited and with the thigh highs and gloves all on I request his help to zip the back of the bodysuit. As he zips it up my caged cock barely pokes out from the bodysuit once it's fully on, he slowly pushes me to my knees and comes down with me.

He starts touching me all over once again once time feeling the latex surrounding my body. He instructs me to get on my hands and knees but to pull my right leg up, I do as he says. The rope goes around my right leg and around my right thigh tying them together. He then puts more rope around my upper thigh and waist. He instructs me to do the same with my left leg which I do, and the process is repeated.

"Stay on your knees but pull your body up and be straight." He orders me and I do as he says. He puts the rope around my neck like a collar with one end long enough to wrap on the opposite side of my body, I feel it lined up with my ass. As he tightens it I feel my plug being pushed in more, as he continues to tie me up. He takes each hand to my left then right side tying it behind my back. "This position is called, seiza. It's one of the positions you circled on the contract to be tied in. What do you think?" He asks me this while he touches my body more, this time in a sexual way reaching for my crotch. He pulls my gag out, expecting a response. I stay silent as he gropes me, all this feeling so erotic I have no words. I just want to enjoy the moment. As he caresses my body, I see him very visibly getting hard, I try to ignore it but he catches me looking.

"Do you want to see it?" He asks me but I know he'll show me regardless of what I say and I'm right as he starts to pull down his pants and underwear revealing his hard cock. It's normal in size, he sits close to me still caressing my body and getting in front of me. He starts to stroke himself then jerks off in front of me. "Note that I have no desire to fuck you, however, I can't ignore the fact that you look better than most real women I see daily. It was never in the contract, but have you ever thought about sucking a cock before?" His question strikes me hard, I feel like I have no choice but to answer truthfully, "Many times but I don't know how." A smile runs across his face, he stands up and I'm met with his cock a few inches from my face. "Do you want to try it?"

I stare up at him and slowly open my mouth submitting to him. His hand gently grabs the back of my face and pushes me close to his cock. The tip goes in my mouth, we start slow. I lick it with my tongue for a bit before more of it is pushed into my mouth. My eyes shut as I start pushing myself into his cock taking more of it, suddenly I feel his balls and my eyes open wide causing me to gag and pull off. He lets go of my head and I cough profusely.

"Don't think about it boy, keep your eyes closed if you want or just look at me." He encourages me, and I open my mouth again this time taking it back in my mouth without his push. His hand still reaches for the back of my head as he guides me. I keep looking at him as he smiles and whispers words of encouragement. I bob my head on it taking more until I feel a slight push from him helping me reach his balls once again.

This time I try to maintain eye contact with him. "Good boy" his hands shifts to hold onto my hair, and he grips it tightly, I bob my head on his cock with him maintaining control of my speed. We have a rhythm broken only when he pushes my face into his balls and keeps it there for a few seconds before pulling me back. He pulls me all the way out as spit and drool come out of my mouth and contact with his cock. I want it so bad and push myself forward, but he holds me back. I look back up at him, "Please." I whisper and he grins "beg for it." I look at him with sad eyes, "Please let me suck your cock, sir." He frowns and I correct myself, "Daddy, please let me suck your cock." His grin returns and the force of me trying to suck his cock with him loosening his grip to hold me back causes me to deepthroat him, I gag but he holds me in the position. Spit pours out my mouth and onto him, as I try to get free. He pulls out and starts jerking his cock off in front of my face, "Daddy please cum on my face." I tell him without any persuasion, he smiles at me as he holds my hair making my face in direct sight of his cock.

I notice a twitch and a burst of cum spews out right on my face across my eye. More cum shoots out, and ropes of cum lay across my face. "Clean it, boy." Without hesitation, I take his cock back in my mouth and lick off the cum and swallow. Once cleaned he pulls out my mouth and sits in the chair across from me while I kneel still tied up but with ropes of cum all over my face. As he breathes heavily, he looks over to the clock, "Good job slave believe it or not it's almost 9:00 pm. I think I should get you ready for bed." Excitement came over me as we discussed how I would be tied up when going to bed, it wouldn't be anything special but the thought of it excited me a bit.

He leaves me in the living room to clean himself up, when he returns, he unties me and instructs me to strip then follow him to my guest room where I will get ready for bed and get dressed in the lingerie, I brought for sleeping. I do as he orders sadly taking off the latex and following him to the guest room where I'm greeted by the nice-sized bed with leg, wrist, and neck restraints. I smile and he says, "Please use this bathroom to get ready for bed you'll notice your bag is here, once you shower, and do your nightly routine I expect you in your lingerie, face down ass up on this bed by 9:45 pm." He slaps my butt and shuts the door, I waste no time getting ready for bed, he made me remain in chastity which brought some challenges, but I get ready for bed after taking a shower, brushing my teeth, etc. I put on my G-string lingerie set with a garter belt and thigh highs, I lay on the bed face down ass up by 9:40 pm. Right at 9:45 pm the door opens back up and he enters wasting no time to restrain me in the bed. He starts with my feet, then moves to my wrists locking them in place. Next comes to neck restraint which is tied to the bed frame. He locks it leaving some give between the collar and the chain attached to the frame. When finished he spanks my ass a few times and I cry out.

"Ah!, Ah!... Ah!" with each hit he brings I'm reminded of the paddle and try to keep my groans to myself.

"You did very good today boy, tomorrow we'll up the pressure, so I suggest you get plenty of sleep tonight. I will wake you at 8:00 am sharp, I have a great day planned for you." He ends with spanking my ass harder than before, turning off the light, and shutting the door. I reflect on the day and everything that took place as I doze off to sleep awaiting the next day.