tagTransgender & CrossdressersTell Me About Your Day Ch. 02

Tell Me About Your Day Ch. 02


In the first chapter, I moved in with my boyfriend and livened up our sex life considerably with a game where we tell each other about our day while trying to get the other person off. Whoever cums first had to make dinner, I say "had" because we came up with a different game to replace it.


"Yes, this is Alex, I am on the line," I said into my bluetooth headset as I closed my eyes and tried not to moan while the boy slowly pushed his cock into my waiting hole. I was on my hands and knees on our bed with him behind me one hand on my hips guiding his cock back home in my pussy and the other fixing his headset in his ear as well.

It was Wednesday, which meant we both were working from home though we still had meetings to call into every few hours. It so happened that both he and I had meetings around the same time, which meant that our new game would involve him fucking me slowly while we were both on our calls trying to get the other person to slip up and make an inappropriate noise.

We had been doing our Dinner game for a few months and I had been winning on a regular basis. When going down on him I started teasing his own hole with a finger or two, he was reluctant at first but between trying to describe his day to me and my having his cock deep in my throat he could hardly object if I started rubbing his behind as well. And I could not help myself as it was really super effective on him, first just rubbing the outside with a wet finger, then after a few weeks I moved to slowly opening him up and when he started getting used to that, I moved on to find his prostate and give it just the slightest nudge when I could sense him getting close.

Needless to say, he was cooking most nights of the week. Since we started he had learned to cook a bit, though we also ate out many nights when he was too tired to cook and really he was not meant for the kitchen. At about the same time, he got promoted at work with a big salary bump and started trying to convince me to quit my job and go full-time as a girl at home. I had considered it, but I hated the idea of being a kept woman even if I did want to go full-time. I explained to the boy that I had no idea what I would do at home all day by myself and his only response was "I am sure you could find ways to keep yourself busy."

That said, my job was the only thing keeping me in boy mode these days and it was a drag, but I was not sure if I left now I would be able to rebuild my career later. So we had a stalemate on our hands.

One day, the following winter, I caught a pretty nasty cold and the boy stayed home to take care of me. Despite being sick, we had a pretty large project at work that we were close to shipping so I tried to work from bed and dialed into meetings. It was during one of these calls that the boy came into the bedroom, pulled back the covers and started to massage my chest.

"What are you doing?" I asked, having put my phone down.

"Just pay attention to your meeting, dear." he repied with a sly look on his face. Meanwhile, someone on the call was asking for me so I grabbed my phone and quickly responded.

"Yes, I am here. I think we can do that by next week..." As I said this the boy moved to take one of my nipples into his mouth and agressively start sucking on it like a hungry baby. I put my hand over the microphone on my phone and snarled, "Stop that!" but he just looked up at me with the most innocent eyes. This continued for a few minutes, progressing to him biting my hard nipples as I tried to explain why we were behind on deliverables. I had thrown my head back with my eyes closed, trying to focus on the call while the sexual tension in my body slowly built. After a few minutes I felt his mouth leave my breasts and I could no longer feel his breath on my chest. I breathed a sigh of relief until I felt him lift my hips off the bed and pull down my pajama pants and panties in one fell swoop.

"Uh, uh, no I do not think that will be a blocker for us," I said as I felt his fingers massging the cheeks of my behind in concentric circles. "We are just waiting on the vendor to DELIVER" I stressed the last word hard as the boy's tounge touched up against my rosebud.

"Are you all right?" someone asked on the call.

"Yeah, sorry, this cold just knocks me out sometimes" I quickly responded as my cheeks flushed and the boy pushed his tongue farther up my pussy. I covered the microphone on my phone with my hand again. "Are you trying to get me fired here?" Again, he just looked up at me with those mischevious eyes while his tongue was touching all corners of the insides of my hole.

And so our new game was born, I would go back to making dinners and lunches so long as I wanted to keep working, and every Wednesday we would both "work" from home and tease each other whenever we had a phone call.

When he had a meeting, I would usually tease him with my mouth, though I tried a variety of other things as well. Pretty much any warm part of my body that I could use to tease his cock had been tried. He responded best to the time I gave him a foot job wearing silk stockings he bought me in Europe, even going so far as to lick his own cum off of my feet once he was done with the call.

When I had a meeting he would usually repeat the initial call that started our game, with him playing with my breasts or with my pussy. Some days when he was extra horny he would wait paitently with his cock right in front of my face and I would open my mouth wide whenever I did not have to speak for him to rub around inside while I listened to my call. If I pushed my tongue against the tip it meant he had to back out so I could say something, If I was feeling adventurous though, I would tell the people on my call I was eating lunch, take his cock deep in my throat, and only respond to the call with affirmative or negative grunts.

He never fucked me though, we saved that for whenever we both had a call at the same time. We had to be extra careful, as we both responded the most vocally to this. Neither of us could move very quickly, no hard thrusting, and usually we would come together in one of the many positions we used while I would just massage his cock with my ass muscles and he made very slow gradual strokes. My favorite position was to ride him so that if my call ended early I could pick up speed raising myself off of him and back down again forcing him to work extra hard not to make a noise.

That brings us to today's call, where I was on the bed doggy-style and he was behind me. I was wearing a pink bustier with garters, stockings and heels. We had played earlier (when I said "work" from home before, the "work" really meant fuck like rabbits) so my hair was a wild mess.

"So we are just waiting on..." I started to say as the boy bottomed outin my pussy. This was one of my favorite moments, when his cock touched that specific part of my insides on the first thrust. That feeling alone, with the anticipation building up as he slowly pushed into me inch by inch, always made me so incredibly happy and fulfilled. But I had to focus! "...oh, nevermind it sounds like everyone is here. Okay we can get started."

I turned my head back to look at him as he spoke softly into his headset for his own call. We had to both speak quietly so as to not be heard on each other's calls, which added an extra layer of tension onto our game. He had both hands on my hips and was pulling back out maybe a millimeter every second. I gave his cock a couple good squeezes with my spinchter around the point he was half way out.

"Yes, we ran into some complications," I said as I noticed he had stopped pulling out. I squeezed his cock again and looked back to see his own eyes were closed as he was in the middle of a long explanation of something. "But I think we can give a strong push and get back to where we started." As I said this, I thrusted myself back all the way on his cock until he was all the way in me. When I turned my head his eyes were bulged out and he was gritting his teeth while I gave him a wink.

"Once we get to that point, I think we will be able to have something to turn over..." as the last words escaped my mouth I suddenly felt myself being lifted off the bed by him, his cock still hard inside me, and flipped over until I was on my back. "... something very soon."

I wrapped my legs around his waist and pulled my body up off the bed until I was almost face to face with him. His eyes were locked on mine, and I so wanted to just kiss him right then and there but he was in the middle of another explanation and I had to listen to my product manager go on and on about something that I could not care less about at that moment.

When he finished speaking I felt his hands go underneath my bottom until he lifted me up off the bed again. I wrapped my arms around his neck as he picked me up until I was floating in the air hanging off of him. I tried to raise myself up off his dick a bit as his nipples rubbed against my breasts through my lingerie. "I Just do not want to raise expectations beyond what we can deliver," I said.

I looked into his eyes again as he was wrapping up his call with some closing remarks. I slid back down fully impaled on his magnificent rod again and leaned back until my arms were fully stretched around his neck and I was at a 45 degree angle from the bed. I was squeezing his cock as hard as I could with my ass (which, I have to admit was pretty hard. You know those long tubular cookies you can get at the store? I have trained myself such that I can open myself up enough to insert one half way, and then close myself around the cookie breaking off half inside of me, which the boy then gets to go retrieve with his tongue before we share.).

As he finished his call he grabbed his phone off the nightstand and quickly turned it off. He lowered me back on the bed and moved my legs up to his shoulders. I rubbed my stockings against his neck, knowing that this drove him crazy, as the product manager on the call was doing a final rundown of everyone's blockers. The boy started picking up speed now, all the teasing up until this point having built such amazing sexual tension within him I think his cock could have drilled through concrete as he thrust in and out of me. I tried to reach backward for my phone to mute it, knowing that whenever he starts thrusting like this I would start moaning very loudly but he pulled me closer to the edge of the bed until my phone was just out of reach.

I had to do my best to contain myself from screaming out as his cock was massaging my g-spot continously now. I grabbed one of his arms from my side and bit into it to keep myself from saying anything, the pain only seeming to double the intensity of his thrusting.

The seconds seemed like hours as everyone else on my team were describing their needs. It occurred to me that my needs were all focused on the boy, on making him happy and being the best girlfriend, lover and whore for him whenever he needed. As this thought washed over me I felt myself let go as I came with the biggest orgasm of my life.

My clit gushed cum out for the first time in months, and I felt it spurt all over my chest, my bustier suddenly warm and wet. As I came my ass muscles contracted even harder than before around the boy's cock as I felt him getting close as well. And then finally it was my turn to speak, the product manager saying my name as the boy thrust up into me to the hilt and erupted his own orgasm painting the insides of my pussy with his boiling hot cum.

"Alex, what are you waiting on? Do you need anything?"

"No... no. I... I think I have everything I need right now."

The boy was still shooting inside me as the call finally ended and he remained hard enough to stay inside as we both took a long breath. I looked up into his eyes again, and he back down at me.

"So I guess I will be quitting after all."

"Oh really? I thought you said you would be bored at home all day."

"Just.. shut up." I said as I pushed the bluetooth headset out of his ear with my stockinged foot. "When is your next call?"

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