My name is Tom, but you can call me Susan, Emily or whatever other role I get to play. I am 19 and always had a pale petite feminine body. I barely have any body hair on me and can't even grow a beard. My dick is pathetically tiny but nevertheless gets hard very easily. I wear my brunette hair at shoulder length which further underlines my girly appearance. I kind of like it that way and although teenage years were awkward I managed to pull through thanks to my best friend Steve which I knew since childhood.
I knew I was gay pretty early on and kind of had a feeling that Steve was too but it took us all the way until we finished high school that our platonic friendship grew into something more. We talked about everything so naturally we also talked about what aroused us and it led to jerking off together, then touching and finally Steve had to admit that he was gay too and our friendship was now even deeper than ever before. Steve is a muscular athletic guy with brown hair, tanned skin and a perfect huge uncut dick. He has a hairy chest and overall looks like a perfect alpha-male but inside he wants to be a sissy dominated by his partner. I kind of feel the same as Steve and also want to be a sissy sub but I don't want to lose Steve so I play along being the top part of our relationship.
I find it difficult to find other gay relationships being rather introverted and still living with my parents. I also truly love Steve and therefore I am thinking that having this kind of sex is better than no sex at all. I didn't come out to my parents yet and I regularily sleep over at Steve's house so we can live out our love.
Steve lives with his divorced father Mr. Joseph Robertson since he too can't afford an apartment of his own while being in college. Mr. Robertson is 45, dark haired, hard working and slightly overweight. He has a balding spot on his head, a hairy chest, and an average length but rather girthy uncut dick. I know this because in summer we use to hang out naked in the backyard at their pool. Mr. Robertson is quite relaxed and knows that his son is gay. He was always very accepting and very kind to me too. Nevertheless Steve insisted that his father is rather macho and conservative inside. Because of that fear Steve only managed to come out to his dad pretending that he himself was the strong alpha male and I was the little girly sissy in our relationship. That way it was easier for him and his ego and since then I have played along.
In fact I was rather happy that during the coming out of Steve he openly forced me into the role of a sissy in front of his dad. I only wish that this would continue in the bedroom, which so far didn't happen.
For the last few months I have been sleeping over at Steve's family house for most nights. The atmosphere is definitely more relaxed than at my home and we certainly don't hold back on our noise while in Steve's bedroom but not getting my deepest desires fullfilled has left me more anxious and frustrated lately.
This evening is no different as Steve is snoring gently in his sleep. Laying there with a satisfied smile on his face he will surely have a good night's rest. Me not so much. I just couldn't cum while fucking him just minutes before and now I lay here with my throbbing hard-on unable to sleep feeling the growing hole of unfulfilled desires inside. I could jerk off myself but the motion would rock the bed and possibly wake Steve. I don't want that. It is hot, I can't lay here anymore. I have to get out.
I stand up in my white boxerbriefs and sneakersocks and quietly move out into the hallway. Ah good! A breath of fresh air. It is nice and cool and it doesn't smell of sweat and cum which I didn't even notice before getting out here. I decide to get myself a drink so I quietly move down to the kitchen. As I approach it I see light in there. Mr. Robertson is sitting at the table in a brown comfy bathrobe and slippers sipping on a beer. I walk in and get myself noticed.
He looks up smiling warmly.
"Tom, hi! Up so late?"
"Yeah! Couldn't sleep. I just wanted to have a drink, if that's ok?" I point to the sink.
"Sure go ahead! I can't sleep either." he takes another sip of his beer.
"Why is that?" I ask while I fill myself a glass of water. Mr Robertson lets out a deep sigh.
"Well you know how it is. Late at night, you think about things, life, relationships, all kinds of weird things..."
The last bit had a strange ring to it and the sentence hung unfinished in the air. I stand around in front of him sipping my drink, not knowing how to reply to that. Thankfully my hard-on has subsided due to the diversion and now it is only a little buldge filling my boxerbriefs nicely as if my penis is actually bigger than it really is otherwise. Mr. Robertson seems to struggle to come up with something to say as well it seems as I watch his watery blue eyes flicker over his beer can in the dim kitchen light. Finally he opens his mouth again.
"So you like to dress up as a girl?" he asks softly. I feel a blush starting to rise to my face. I clean my throat.
"I - erm - that is what Steve has told you, I asume?!" my voice a little higher than usual. Steve was so ashamed to come out to his father that he couldn't bear telling the whole truth so he said he was the dominant part of our relationship when in reality he is not in the slightest. He thought that his father would easier swallow the news of him being gay that way and since then the topic never came up again. In our room I never got to play the bottom part but in front of his dad we at least pretended it. Again there is a brief pause from Mr Robertson.
"No. actually that is not what he said. He, he just said you would like to be a girl, if I remember correctly." he looks up to me questioningly which causes my blush to fully emerge. I can feel my cheeks glowing.
"Well, yes. That is correct." I say holding his stare.
"That's fine. I am totally fine with that," he adds reassuringly as he sees me blushing. "I was just wondering, since I never actually see you wearing anything girly around here."
'Oh my god!' I think to myself, maybe he suspects that Steve is telling a lie, maybe he knows, maybe he has heard or watched us. The color leaves my face again but I try to remain calm. I don't want to ruin this between Steve and myself, I have to keep the story up.
"I don't have any girl stuff!" I blurt out. "I still live with my parents and they don't know that I would like to - be that way. I am not ready to tell them." I breath in. "But I would really like to dress up. It's just not so easy given my situation." I add. Mr Robertson nods sympathetically.
"I see." he mumbles taking another sip of his beer. "Well if you want to try it out here around our house feel free to do so. No need to worry here about anything."
"Th...thanks Mr. Robertson. If - if I can get some girl clothes secretly I will do that in the future." I smile and thoughts run through my head how I will tell Steve about this conversation and maybe he is willing to upgrade our coverstory and I could really dress up when I stay over for the weekend. The possibilities make my little cock twitch again rubbing a bit against my white cotton briefs. I smile involuntarily at the thought as Mr Robertson who is watching me adds.
"Actually I think my ex-wife left a bunch of her stuff here. She was petite, just like you, maybe you would like to try some of her stuff out?" My jaw drops down hearing that offer. A rush of excitement floods through me and my heart starts to race faster. Oh god I will never be able to sleep now with all that possibilities in my mind.
"R..really? That - that would be great!" I almost moan out. At least my coverstory got 100 times more believable with my last outburst of excitement. Mr. Robertson finishes his beer and stands up. His mouth still full he gestures me to follow him which I do. He switches on the light to the basement and unsteadily walks the stairs down in his slippers, his plushy beige robe gliding behind him. On silent toes in my white sneaker socks I follow him down.
He leads me into a cool room with a brown tiled floor and switches on the light. This was once a partyroom it appears. On one side there is a wooden bar setup with cabinets and barstools and a seating arrangement with a table next to it. The rest of the room once seemed to be a dancefloor with small coloured discolights in the corner and mirrored tiles all over the ceiling. Now there is all kind of junk and boxes piled up, a weightlifting bench, a stationary bike, it sure was a little fitness room at one point too. The air is cool and a little moldy but not bad. I can feel the cold hard tiles through my socks and dance around a little from one foot to the other. Mr. Robertson rummages around at all the boxes and suitcases lined up around the seating area. Finally he finds a medium sized dark blue suitcase which he pulls out and lays on the table of the seating area.
"There it is." he also sounds rather excited as he zips it open and opens the lid, then steps aside. I gasp. It isn't just full of old women's clothing. Actually I can immediately see there is some lingerie, stockings, and really fancy stuff presented to me. I take a step closer.
"Wow." I say in a whisper. Mr Robertson scratches his neck nonchalantly.
"Yeah. My wife was quite foxy when we were younger. Had a lot of fun together." he sighs, then looks hopefully up at me and smiles. "Go ahead! Don't be shy!" he gestures towards the open suitcase and sits down on the weightlifting bench watching me. Again I have to blush but I grab a piece of purple lace fabric and feel it between my fingers. It is a fine lace thong, very soft.
