More Non Consensual Than Intended

Editor's note: this story contains scenes of gay male sexual content.

Warning: This story is about an agreement to indulge in a non-consensual fantasy that turns out to feel a lot more non-consensual for our hero than he had initially intended. If simulated rape is not your thing, please do not read. It may be a little too rough for some.

*

It was one of those rare times when I had the day off work, but my wife was working. I was looking forward to sleeping in and then taking advantage of some alone time. As it turned out though, I did not sleep as late as I thought I would. I got up, grabbed a cup of coffee and sat down at the computer. I to check email, the morning news, and finish my first cup of coffee before taking a shower. My plan was to take a shower, clean inside and out, and then take the opportunity to indulge in a little cross dressing. I really wish I had more clothes but since I was still hiding this aspect from my wife, I only had a few frilly lingerie items and stockings. I fantasized about having more: shoes, skirts, blouses, and even a wig. I was too chicken shit to get those items. So, I was stuck with dressing like I was ready to be taken to bed and so far, that had been enough for me. I know how it would work out. I would dress, play with a dildo and/or butt plug and watch porn until I got all worked up and masturbated while fantasizing about being with a dominant daddy type.

Even though I was married for over 20 years, I did have some encounters in the last 10 years. Very few and far between. I had given head a few times but not more than that, I was still a virgin when it came to anal sex. I love my wife and can't picture being in a romantic relationship with anyone else, let alone another guy. However, the thought of being in the feminine and submissive role with another man is one of those fantasies that was pretty standard for me. The fantasy would wax and wane and like the phases of the moon, as sure as it would wane, it would also come back, shining bright as dominant fantasy for a time.

Sipping my coffee, I noted nothing new in email and the news was the typical boring stuff. I finished the coffee, and headed off to the shower, looking forward to my date with my inner gurl. I took out box that I hide my girl clothes in and set out the stocking, panties, and lingerie on the counter. I got the lube and toys and set them out on the bed. I knew my wife had a long day at work and would not be home until 9:00 PM so I was not worried about her finding the toys on the bed while I was in the shower.

The shower attachment was such that I could unscrew the head and I could use the hose to give myself a warm enema. Whenever I would play with toys, I liked to be clean inside. I would step out of the shower, evacuate, and then repeat until the water came out clean. I took the razor and shaved smooth any stubble since the last time I shaved. I have been shaved clean for years down there and preferred it that way; not just because of my feminine inclinations but it seemed so much more hygienic. I finished up the shower, dried off, brushed my teeth, and then shaved my face. Then I proceeded to dress up in my girly clothes. As I put them on, I felt more and more feminine. I selected black lacey baby-dolll lingerie, thongs, and some smooth, black stockings. Having the whole day to myself, I was not in any rush whatsoever so took my time to enjoy the feeling of the sheer nylons and frilly clothing.

I went back out to the living room and brought the laptop back up. Surfed to my Tumblr blog. I follow many people that post on Tumblr; most of the blogs revolve around sissies, chicks with dicks, and wife sharing themes. As I went through the new posting and following links to interesting new blogs, I would occasionally caress myself through my sheer garments, pinch my nipples, and envision myself in the scenes that I was watching on line getting more and more turned on.

I was about to go get the toys and start playing with them when I happened on a tutorial on how to apply makeup. Well, shit. I have all day. I have tried putting on makeup before and even had a stash of my own from when I tried it the first couple times. I watched the tutorial and decided to try it again. I brought the laptop into the bathroom and replayed the tutorial, following along and pausing the video as needed. I would like to say that I transformed into a hot woman but... it was a lot better than the first couple times. Not entirely passable in the light of day but the tips I followed in the video defiantly helped with bringing out and highlighting my feminine features. I was enjoying the feeling and took a couple selfy pictures. I am sure that I would delete them later so there would be no chance of my wife finding out.

So, I found myself in the bedroom, towels spread out on the bed, toys and lube at the ready. Readying to seduce myself. I went to turn off the PC and saw that I had one unread email. I opened the inbox and saw a message from Steven. He was writing to tell me that he was looking forward to when we can finally meet. He went on to suggest a scene that we might eventually play out once we do meet. This was not at all unusual and would often lead to another shared fantasy scene for if we could ever meet in real life.

A little history about Steven... Steven and I initially connected through Craig's List before they shut off the personals section. We exchanged email addresses and had been writing on and off for over a year or more. He and I had been emailing each other fantasies and trading ideas about what we each found to be erotic. We would also recount past and what we liked experiences and did not like about them. He and I fit each other's desires well. He was a top only but liked sissy boys and he was also into couples. This really caught my attention, not just because I was a fantasy sissy but also, because one of my biggest fantasies is my wife being a slut for another guy. This fantasy developed over time but as I learned to accept my curiosity and bi tendencies, the more the idea of being cuckolded become more prevalent in my fantasies. He and I met one time but just to meet in person and get a feel for each other. We talked for 45 minutes and we both agreed that we were still comfortable with each other. He was an attractive guy, in decent shape, and clean cut. What I found attractive was mostly his confidence in himself. He was more of an extravert than I was and was easy to like. Though our emails and chats, it became obvious to me that he would prefer a couple but would be open to having a sissy friend too. We had a lengthy shared fantasy in writing in which he would seduce my wife, Maureen. How he would take her out after work for coffee and then seduce her into being his lover. Although it was fantasy, it was also somewhat rooted in the realm of reality... but only if Maureen was interested. We both lamented that my wife seemed to just not show any interest in that area. I had brought up the subject to Maureen a couple times, but she didn't give any indication that she was or was not open to the idea. So, unless something changes, the only possibility of any sexual activity would be just between Steven and me.

I stared at the email for a moment deciding on if I should reply or continue with my plan for self-indulgence and respond later. I replied, telling him that I was enjoying the day to myself and added one of the pictures that I had taken just a few minutes earlier. He replied after just a few seconds asking when that picture was taken. "Now" I replied in one word.

His next email came after about ten minutes. I re-read it a couple time to make sure I was understanding correctly. He said that he wanted to rape me and was willing to pay me for it. He went on to explain that he was in the mood to fuck someone hard without regard to their feelings about it. He said that the pictures I sent showed him how much I wanted to be dominated and just how much he wants to be the one to so it.

My mind was racing. The idea of whoring myself out like that has always been a turn on. However, I was not sure about the rape part. I replied saying I was not sure if I would be into the rape but a little rough would be good. I mentioned that it might be hard to rape the willing. But I was curious as well and asked how much he was looking to pay.

His reply was surprising. "$2500. No permanent marks. No lasting damage. It will hurt and your ass will be sore for a couple days."

I sat there stunned. Through our previous emails in the past, the subject of borderline non-consensual play had been discussed at length. I knew that the idea turned him on and I had admitted that I was intrigued and to it, but I was just not sure how much. But he had now put a price on it. Shit, was I really considering this? I was. I replied to his email with a "Yes, when?" I added my home address. My hand was shaking when I hit the send button. What had I just committed to?

I got one last email saying that he will be there in 30 minutes.

I was a nervous wreck. I checked myself in the mirror, checked the makeup, straightened the baby-doll and waited nervously for his arrival. I then though that I should get ready. I got the lube out of the bedside table and then it occurred to me that I should loosen myself up. I did not know how rough he might be. I got the butt plug out of the bedside table, covered it in lube and slowly inserted it. As the wide part started to enter me, I felt the sting of it. I pushed past that and felt it pull into me. The whole time, I was wondering if I was ready for this. I was selling not just sex but my virginity for $2500. I understood that I would be getting used and that I might not enjoy it on a physical level but could not deny that the idea of a man, using me in such a dominant way, was a huge turn on. After all the secret desires that we shared as well as long email threads about life, relationships, and daily life, I felt like I knew this man well enough that I felt comfortable enough to trust him enough to be this dominant and that I would not regret it later. I knew that might regret it if I had let this opportunity pass.

20 minutes later, I see his truck pull up to the house. I get up and before he knocks on the door, I open it, inviting him in. I hide from view behind the door, so the neighbors don't catch a glimpse of me in lingerie. Steven comes in and looks me up and down. I reach out to shake his hand. "Glad we could get together," I say somewhat awkwardly.

Steven looks at my hand, smiles, and pulls me in for a hug. "You are such a naughty girl. Inviting me over like this and being all dressed up for me." Initially I feel awkward in his embrace but then feel my feminine side slipping into the role. I return the embrace and somehow his body seems so masculine against mine. Steven smiles at me we break the embrace and tells me turn around. Feeling his eyes one me, I try to pose and turn, becoming excited at this really happening.

After turning the lock on the door, I take his hand and lead him into the living room. "Can I get you anything to drink?" I offer.

"I'm fine...but there is something you can do for me," he says suggestively rubbing his crotch. "Which way is the bedroom?" he asks.

"Right to it then? How much time do you have?" I ask nervously. I am hearing myself say this and feel slutty in just how much I want to finally consummate this relationship... what ever it is.

"I have about 2 hours free and clear but do have plans this afternoon," he says. "We do not need to rush anything but don't have all day either." I point to the bedroom door and he takes my hand and leads me in there. There was something incredibly erotic about that, being led by the hand to the bedroom when I know what's going to happen. Stepping into the bedroom, he tells me to get on the bed. I do. I crawl up onto the bed on my hand and knees and that's when he notices the butt plug. "Oh, it looks like you like your pussy filled," he said reaching out and moving the thong to the side. Hope you have a condom and lube ready."

"I have lube but have not needed a condom in years," I said.

"Well, I will leave it up to you then," he said. "I feel that I know you pretty well and through all the emails we have exchanged, I feel like you have been honest about being healthy. But its okay if you don't feel the same." He took out a handful of folded bills and put them on the bed.

I thought for a second. Seeing the money made me feel more slutty than I had imagined. I did trust him. We not only shared fantasies with each other but shared past experiences and life in general. I felt that we had developed a friendship in its own way. I crawled over to the bedside table and opened the drawer, fished through the assorted toys, and got the lube.

"I see you have some restraints," Steven said as I started to shut the drawer. I opened it back up and took out some padded cuffs and ropes. Steven held out his hand and I passed him the cuffs to inspect. "Nice. Does my sissy boy like being tied up?"

"I do," I said, "but I am not so sure about it right now." The idea of being dressed in this baby-doll outfit and being tied up was tempting but thought better of it. "Not that I don't trust you...but...," I shrugged.

"No worries," he said, "but how about just a little bit? I'll give you anther $50."

Curious, I asked, "What do you have in mind?"

"Just the hands." He said. "Even if I were to up and leave you, you would not be stuck... I promise."

"Okay," I agreed hesitantly, "but how about a safe word?" I was starting to worry I might be getting in deeper than I had intended.

"Safe word will cost you $1050," he said laughing, "I like the idea of there being no escape but will leave it up to you. You will still get $1500."

I thought about it for a second. I might have been making a mistake but opted for the cash. Shit, I really was a whore! Besides, I trusted him, knew that this was going to be a real experience, it would not be for very long, and perversely really looked forward to seeing what it would be like to be brutalized.

Steven had me get off the bed and stand on the floor. He took my wrists and fastened the wide cloth cuffs on each wrist. He then clipped on the ropes and told me to bend over the bed. He walked around to the other side of the bed and pulled to ropes tight, so my arms were straight out in front of me on the bed. He then tied the other end to the frame of the bed. It felt vulnerable in this position, bent over the bed like that but I would be able to easily crawl across the bed and undo the cuffs myself so I didn't feel threatened at all. I was standing on the floor with my legs only slightly spread. At 3 ½ feet off the floor, it was about the perfect height for this and my torso lay flat on the bed .

Steven came back around and behind me. He caressed me through the lacy material of the baby-doll outfit. "Oh hell," he said, "I should just tie up your legs and fuck you hard like the slut you are." His hard cock rubbed against the material of the thong.

I felt a little panic welling up.

Steven laughed, "Don't worry baby. I was only teasing. When you are ready, we will play that game." He slapped my ass with his cock in a playful way. I felt relieved. I felt him lift the skirt part of the lingerie I was wearing, exposing my ass to him. Then he slipped the thong down over the nylons I still had on. I stepped out of then when they hit the floor. "Bet you would look really hot in some high heels," he suggested. "Take some of that money you earn and buy yourself some nice high heels."

Oh shit, I did like that idea. Embarrassment had prevented me from buying my own and I certainly not order them on line without Maureen possibly finding them. But there was something about it pleasing him that made me decide that I would do just that. "I would love to wear them for you."

I heard him behind me taking is pants off. I tried to turn to look but couldn't look around with my arms being pulled tight out in front of me. I felt a sight twinge of panic thinking that I had not seen his cock in real life before. Sure, we had traded pictures and he said that he was 7 inches. But what if...

He pushed in on the butt plug that was still inside me and said, "From here on out, I want you to tell me no." He moved the plug around and then suddenly pulled it out. "Are you ready to be fucked little girl?" he asked.

"No," I said obediently.

"Good. You catch on quick. Do you want daddy to fuck you with his big cock?" I was actually looking forward to it and was starting to think that, even though I was making money from this, I might end up liking it a lot more than he thought I would. "No, please, I don't want to be fucked," I tried to say with a little conviction, "it's too big."

I felt the tip of his cock sliding up and down the crack of my ass. He dripped more lube on the head as he moved and when the tip grazed over my rosebud, I felt a tingle all the way up my spine. "You want this?" he asked, pushing slightly when at the opening.

I moaned in response and tried to push back a little. I wanted to tell him that I did, but instead I said, "No, please don't." I said. I was almost afraid that I was sounding a little too convincing. Since he started slow. I was a actually looking forward now to being hurt! He applied a little more pressure and I felt myself starting to yield to him. At any second, I was no longer going to be a virgin.

Suddenly, my phone rang on the bedside table. Oh shit, what bad timing! But I had to see who it was just in case. "Who is it?" I asked Steven.

He looked down at the phone and said "Maureen." He picked it up and for a second I thought he would answer it! He then put it next to my head so I could see it. "Would you like to answer it?"

She was at work and would not be back until late evening but she would only call if there is something that she needed. "Fuck, I have to," I said but realized that there was no time to untie me. "Put it on speaker but be quiet. Please be quiet," I begged.

Steven hit the answer call and put it on speaker.

"Hi honey," I said.

"Hi," she said in a playful tone. "Are you busy?"

Maybe she has a chore for me to do while she was at work and she figured that she would call before she forgot about it. I considered telling her that I was a little tied up, enjoying the pun, but thought better of it. "Nah, just hanging out," I lied, "what's on your mind?"

Steven pushed the head of his cock into me! I audibly gasped at the sudden intrusion. I could not believe that he was pushing into me right then with my wife on the phone! It was amazingly hot but at the same time, I was terrified that any noise might give me away. I stifled my gasps.

"You okay?" she asked hearing the gasp.

Trying to control my voice as he slowly sank into me, I replied, "It's nothing, just hit my toe on the doorframe." Another lie. I felt bad deceiving her like that but hell, I was not about to tell her that it was a bad time because her husband, dressed in secret sissy clothes was getting fucked from behind.

Steven leaned over and whispered in my ear that was on the other side of the phone, "liar." He pushed all the way in.

I gasped again. Fuck, that hurt! I was losing my virginity and the split in my attention to talking to Maureen on the phone robbed me of being able to fully take in the sensations of being fucked for the first time. I was disappointed, but it was my own fault, I understood that, so I was not upset with her. But Steven could have waited until I was off the phone. In a way, it was hot, but I might have liked the scenario better had it not been my very first time.

"So, as it turns out," Maureen said over the phone, "I got off work early today and was thinking that maybe we could do something." I felt panic start to set in as I realized that I could hear the background noise of the car. Shit, she's on the way home already! If she just left, I would have about 25 minutes... I hoped.