Robin's Arrangement

"Oh, I hope I haven't offended you. I just find you really attractive and, oh man, I knew I should've waited to say anything to you. Sorry, I'll go. I hope you'll still work for me. And please don't think you have to leave this place." As he said this he stood up and turned to the door.

Seemingly unbidden my hand shot out and grabbed his wrist, stopping him. He spun back, his eyes wild. I just looked up at him and then nodded my head.

He visibly shook, and I could see a wave of relief come over him.

Before I could chicken out I stood up and pulled him across the room to my bed, gently guiding him to sit on it. I took a towel and folded it and put it on the ground between his feet. I then put one hand on each of his knees, looked him right in the eyes and lowered myself to kneel between his feet. Still looking in his eyes, my hands reached for his belt, and worked to open it up. It was a tight space because he was sitting, so he leaned back on the bed to give me better access. I was able to open and unhook his belt, putting the ends to the side.

Still looking him in the eyes, my hands went to work on his fly. I had given a few blowjobs before, but never undressed the person who received them, so I had to work at it a bit, but managed to get the button undone and worked his zipper down without breaking eye contact. I worked his pants down, and he obliged by lifting his ass off the bed slightly. Then I pulled down his boxers, again with his help.

That is when I broke eye contact, to look down at his member. It was semi-hard, and sort of curved through the air, pointing at me. It was a good seven or eight inches, and pretty thick. I took it in my hand and started stroking it, and James moaned softly. Looking back up at his face, I slowly lowered my mouth onto the tip of his penis, wrapping my lips around the mushroom head. I felt him stiffen and grow in my hand, and I gently stroked.

I pushed on his chest with my other hand, encouraging him to lay back on the bed, and he did. Now I could focus solely on giving him pleasure. I popped him out of my mouth and licked down the underside of his shaft then back up. My other hand cupped his balls and gently rubbed and tugged at them. More moaning from James told me I was on target, and I started to use my lips to run up and down the underside of his cock, using my hand to stroke him at the same time.

He started to tremble, which I took as a good sign, and put him back in my mouth, using my lips as I bobbed up and down on him, my saliva lubricating him as I stroked him in time. I don't have a good sense of how long I did that for, but his trembling increased until he let out a sudden moan, almost a yell, and exploded in my mouth. Waves of cum shot into my mouth and I stopped bobbing to focus on catching it all. I kept my lips wrapped around the tip and stroked him in time with his spurts of semen.

It felt like a gallon of cum, but it wasn't so much that I needed to swallow any because my mouth was full. Squeezing the last of the cum out of his member, I did finally swallow the salty load.

He started to soften quickly, and I leaned back on my heels, catching my breath. I hadn't even been aware that I was holding it at the end. James started making noises, and I couldn't tell if he was laughing or sobbing. He pushed himself up and looked down at me, and I could see that he was laughing. It was an expression of pure joy, and it made me smile back at him. He reached down and cupped my cheek with one hand and stroked my face. He had stopped laughing and was just smiling contentedly.

"I accept your offer," I said, and kissed the hand that was cupping my cheek.

Then I stood up, pushing myself off his knees to do it. I went into the bathroom and rinsed my mouth out with mouthwash, then came back into the apartment. He was standing and buckling his belt.

"Those outfits, she left them behind because you bought them, right?" I asked him.

He looked a little embarrassed, but nodded at me.

"Well, that's good to know. I was thinking after my shift tonight I would clean up and maybe try one of them on, if you wanted to come up and let me know how it looks. They all seem to fit pretty well."

He smiled again, and just nodded. There was an awkward silence, which I eventually filled.

"Well," I said, walking over to the door, "I need to go shopping before my shift, so..."

"Right," he said, and followed me. "I'll see you around four then."

When he left, I turned around and leaned against the door. My mind flooded with emotions, everything from elation to relief to awful anxiety. I didn't know if I was making a mistake or not, but it was too late now, I was committed. A great shiver went through my body, like I was cold, but I didn't feel cold. I just felt excited and suddenly tired. Crossing to the bed, I lay down on it. It was still warm where he had been sitting, and I felt that warmth with my hands, connecting to the reality of what just happened.

As his warmth fully dissipated I sighed and stood up. I changed into a dark blue dress and put the gray cardigan over it. The Walgreens was a few blocks away and it was chilly out. I grabbed my purse and headed out.

I just needed some toiletries, and picked up a box of enemas too. I had plans for tonight that included having a very clean bottom, so I would need them to affect that cleanliness. I also picked up some water-based lubricant, which I would hopefully need as well. As an afterthought I grabbed some condoms as well, just in case he didn't show up prepared, or expected unprotected access to my ass.

Thankfully, there was a self checkout and I rang myself up and headed back to my apartment. I was so horny when I got back that I almost cleaned out to play with one of my dildos, but I was able to focus and keep from doing anything to satisfy my urges. Instead I selected the outfit I would wear that night, down to the shoes, and laid it out on the bed. I convinced myself that I had better try it on to make sure it fit, and spent the next half hour getting fully changed into the outfit. The tulle and satin flowing over my skin, and the long sheer hose made me so horny that I actually got a partial erection, something that was becoming less and less common as I continued with my hormone treatment. I played with myself through the layers of fabric, and edged myself continuously for what felt like an hour, but was probably only fifteen minutes.

My phone's alarm beeped, and I snapped out of my reverie, shaking with the nearness of my orgasm. I rolled off the bed and quickly got undressed, laying out the outfit on my bed as I peeled each layer off.

Getting ready for work was harder than usual. I felt kind of sluggish as I cleaned up, brushed my hair, and got dressed. I finished up, and went downstairs. I would be a little early, but there was no sense in staying up here if I could get started on getting ready for my shift.

I went into the restaurant and the place was empty except for the back of the house crew prepping. By the time the other wait staff rolled in I had gotten most of the work done, and we spent the rest of the time leisurely finishing up, chatting and laughing as we did. It was a Saturday night and we were almost fully booked, so we made sure everything was as stocked and ready as we could, so we wouldn't have to scramble in the middle of the shift.

What was nice about a fully booked night is that it goes so quickly, because you are too busy to stop and think, and this shift was no exception to that rule. Before we knew it we were doing our close out tasks and getting things set for the brunch crew tomorrow. I had the brunch shift, so I appreciated everyone being conscientious at the end of a busy shift and taking their time to do things right.

James had been oddly absent most of the night, only showing up around nine. He treated me like he always did, there was no awkwardness over what had happened earlier. We closed out our registers with him and I had to whistle at my tips. It was the most I had ever earned in one shift. I had been upbeat all shift, on a high from the blowjob I had given James before work, and thought that might be a reason why.

I laughed to myself because if that had that effect on me I could only guess what tonight's plans would mean for my brunch shift tomorrow.

I grabbed my purse from my locker and headed upstairs. First things first, I stripped completely and got in the shower, scraping off the restaurant smells from my body. Then I shaved my nether regions, leaving a small patch of pubic hair. My legs were never hairy, so I didn't bother shaving them, and the electrolysis treatments had taken care of what little facial hair I had. Using an enema bulb I'd gotten that day, I cleaned out. It didn't take long before it ran clear.

Next I moisturized, just to get that lovely feeling it brought to me. Then I blew out my hair, brushing it and getting as much body as possible. Makeup came next, taking my time to apply a heavier than usual look, really working on my eyes. They were the feature I thought were most boyish, so I wanted to take the time to make me look as femme as possible.

I texted James then, asked him to come upstairs in twenty minutes. I just wanted to give myself a deadline. I set a timer on my phone for nineteen minutes and hurried to get into the outfit I had chosen. There was a garter belt and white stockings that went on first, then a white bustier. The white lace thong panties I set aside, and pulled out my jeweled butt plug and the lube I'd bought that day. Relaxing myself I worked it slowly in, then once it was in I worked it in and out a few times. There was no pain, just a little tightness that went away as I worked.

Wiping my hands on a towel, I pulled on the white lace panties, the thong riding over my plug and up between my cheeks. Then I looked at the dress. It was a white satin wedding dress, or rather a short costume version of a wedding dress. There was a nylon undersheath, then layers of tulle to puff out the skirt. The waistline was not quite as high as an aline but it was higher than typical. I stepped into it, and slid the dress up my body, sliding first one arm then the other through the puffy shoulders and into the lacy three quarter length sleeves.

The sensations of all the material sliding over my body were driving me mad with sensual pleasure and I felt myself getting an erection again. I quickly zipped up the back and checked my phone. Eight minutes left. There was a response from James, too, a thumbs up in response to my text.

I worked on my hair then, using the veil with its small tiara-like attachment to good effect. I checked myself in the bathroom mirror. I liked what I saw, very feminine and very sexy. I laughed. I always felt sexy when I had a butt plug in, and now was no exception.

One last touch and I'd be ready. I slipped on the white patent pumps. They had a high heel, probably four inches, but weren't ridiculous like some of the other shoes. I walked across to the kitchen table and back, getting used to them. I have been practicing wearing heels since I was eight years old, so I managed a very smooth and feminine stride.

Just then my alarm went off, and I turned on the bedside light and silenced my phone. I went over to the door and turned out the overhead light, liking the duskiness in the room caused by the low light.

I waited then, and the time seemed to trickle by, as slow as the last minutes of a school year ticking away in a classroom. I walked over to the kitchen table and first perched on the edge, then sat down in one of the chairs. The chair pressed the plug further into my ass, brushing against my prostate, which made me hum with pleasure.

A few minutes ticked by, and I started to rhythmically grind my ass into the chair, causing the plug to move around inside me. I closed my eyes and gripped the chair and table, getting truly aroused by the feelings. I was starting to lose track of where I was when I heard a soft knock at the door. I moaned and stopped my grinding and stood up. A few steps over to the door, and I was faced with sudden panic. This was it. I wasn't a virgin, but I wasn't really experienced, either. For just a moment I thought about trying to get out of it, but then steeled my resolve and opened the door, striking a pose.

James just stared at me, open mouthed, staying that way for a good ten seconds. It was long enough that I started to get nervous, and my composure started to crumble. But then he said just one word and came toward me.

"Perfect," he said, and swept me off my feet, hooking the door closed with his foot as he carried me over to the bed.

He gently placed me on the bed then leaned down and kissed me. It was a forceful kiss, one that spoke volumes about who was in charge in our relationship, and I melted into him. He settled down next to me and we kissed for quite some time, his hand roaming over my body, feeling every bit of me that he could.

He slid his hand under the skirt of my dress and felt up the inside of my thighs, then cupped my genitals through my panties, slowly rubbing me. I started to get hard, and he moaned a little, but didn't stop kissing me. Pulling my panties down a little, he pulled out my member and started stroking me even as he invaded my mouth with his tongue. I moaned into his kisses and felt myself go limp in his arms.

He sped up his stroking, and his kissing got more passionate, and I moaned and moaned, completely at his mercy. Then he stopped, suddenly, and it was like a chasm of emptiness my pleasure fell into and dissipated. One more soft kiss, and he tucked my penis back into my panties, and he was off the bed. I just lay there and watched him, completely powerless to move.

I saw him kick his shoes off, then unbuckle his belt and slide his pants off. He pulled his shirt off and slid his boxers down. He stood straight and his penis, seemingly having grown a size since this morning, stood straight out from his body.

He reached down to me and pulled me around, positioning me on my back with my head over the side of the bed. And just like that he slid into my mouth. It was the first time I had done this, and it certainly brought with it some new sensations. He gently pressed into my mouth, and I struggled to control my gag reflex. I had practiced just this with my softest dildo and was proud now of being able to watch him slide fully into me, pressing his balls into my nose and eyes. Then he pulled out again, and slid back in, nice and slowly. The feeling of being filled up was amazing, and I could feel my penis bulge against the lace of my panties. He gradually increased his speed, and I took shallow breaths every time he pulled out, keeping my breathing as regular as possible. He slid in again and again, and by now the familiar feeling of his testicles sliding into my face was massively erotic.

I was a hole for him to use, and so many of my fantasies were fulfilled by that I felt myself getting fully erect. I pulled the hem of my dress up and pulled out my shaft, stroking it as I did so. I heard him grunt and felt his hands on my wrists, pulling my hands away. He stopped stroking in and out of my throat momentarily and repositioned himself. I felt him wrap one hand around my shaft and then he started fucking my face and stroking my cock in the same rhythm. I slipped back into extreme ecstasy and concentrated on staying completely open for him.

I'm not sure how long that went on, but I started to feel an orgasm coming on. My legs started kicking uncontrollably, just little violent shakes, really, and James must have noticed because he stopped stroking me. A few more times in and out and he popped out of my mouth, too. He left me gasping and on the edge of an orgasm, which I felt slowly subside as my breathing returned to normal. My eyes were closed, and I heard him tear off one of the condoms. I was so grateful that he was using one without confrontation that I breathed an actual sigh of relief.

I opened my eyes and saw him rolling the condom up his erect member. I suddenly had a deep desire to have that cock inside me, and sat up, spinning around. I slid off the bed and stood bent over the bed pulling the skirts of my dress up, exposing my ass.

"Fuck me, now," I said, with all the heat of passion I could muster. I didn't have long to wait.

He came up behind me and slid my thong aside, then slowly worked my plug out and then in again. He did this a few times until it went in and out without resistance. I buried my face in my blankets, waiting for him to mount me. I heard the pop of the lube container opening and moments later I felt him press against me, the tip of his cock pushing against my tight opening.

I felt the mushroom tip's pressure on me, and then with a pop, he was inside me, pushing all the way home. I moaned and bit the blanket. There was no pain, just the pleasure of being filled and the bumping of his glans over and past my throbbing prostate. He stayed like that for a bit, flipping up my skirt to expose my ass fully. Then he grabbed ahold of me with both hands and slid slowly out, before sliding in again. Again I moaned, and I heard him laugh. It wasn't a mean laugh, more like an expression of joy. We went on like that for at least five minutes, slowly in and out. Toward the end I started to get too horny and pressed back against him, speeding up his inward strokes.

He gave my ass a light smack, and I subsided, but he did get the message, and a few strokes later he started to speed up. I moaned in time with his strokes, and it got so that my moans turned into short, sharp gasps as he upped the tempo and really started to pound into me. It felt so amazing, and I wondered why I had ever been anxious about this. It was like a buzzing of horny feelings in my belly, struggling to escape. I felt like if I just touched my penis, I would explode all over the place, but I was enjoying it too much to stop it by cumming.

He went on for what felt like hundreds of strokes, and my throat started to get raspy from what had turned from gasps into short sharp barks every time he fully entered me. Then, all of sudden, with a pop, he pulled out. I moaned and my knees started to buckle, but he pulled me up off the bed. Fumbling hands found the zipper and he unzipped my dress, and started to pull it down off my body. Shrugging my hips I assisted him, stepping out of the dress and turned around to face him.

He wrapped me in his arms then and kissed me, a long, passionate kiss that I returned. Then he directed me to the bed and I lay back on it. He took a pillow and propped it under my bottom and got into bed between my legs. My legs were up and bent, opening myself up to him. He didn't wait long, guiding his cock to my pink, tight, ass and popping the head back in. Then he sort of fell forward and slid the rest of the way into me. It felt divine, and I moaned with pleasure.

Slowly again, he started pistoning in and out of me, and I wrapped my legs around him, encouraging him to go faster. Again, he obliged me, lowering himself onto me and really starting to pound in and out, in and out. Soon I was again in that sublime place where I felt like I would explode, except this time his abdomen was rubbing up against me, through the lacy panties. I felt an orgasm building and my breath came in gasps. He seemed to notice and if anything started hammering me faster.

And then I was there, cumming. It was exquisite, the combination of the prostate stimulation and the rubbing against my penis through the panties created a sensory feedback loop that was too much to bear. I didn't quite scream with ecstasy, but it was close to that, and my body bucked under him, my ass clamping down on his hot cock as it slid in and out of me. My orgasm went on for what felt like a full minute, and just as it was starting to subside, he moaned and pushed into me one last time and stopped, clearly joining me with his own orgasm. He started shaking and I could feel his member pulse inside me, wave after wave of his own pleasure ripping through his body.