I’ve known Tony for nearly a year by this point. What a struggle it was for a married crossdresser to find a friend with benefits after the pandemic. Well, I suppose it was difficult before those couple of years, too.
Of course I’m cautious and perhaps a bit particular, but if I’m going to take this adventure, why not go for the best.
Tony is a banker, an upper-level executive working at their headquarters downtown, though these days he’s more often than not still working from home at least half the time. He’s close to retirement.
Tony’s a married man. I prefer an attached guy. It’s just one of the criteria that probably make it so hard to find someone. A married man means safety, for one. He’s discrete and not prone to be bed hopping. I also get a thrill out of being his wife’s competition. The fact that he enjoys me as he does his wife. It’s all part of the dynamic.
My internal dynamic with a man is critical. I honestly don’t feel terribly feminine but when the dynamic between me and a man is right it gets me there.
It’s why I love Tony. Aside from his charm, good nature and good looks, he’s a successful businessman that knows what he wants. And that he wants me, well, you see what I mean.
It also means he pampers me to a degree, paying my way, buying me things, like any gentleman would do for his girl.
In return, Tony knows I’m beholden to him. He owns my ass both figuratively and literally. Tony took my virginity a couple of months into our relationship.
That’s right. At 65 I was still a virgin. No man had ever fucked me. I’d pretty much done everything else one could do as a crossdresser. I mean, nothing creepy or anything. I draw the line at that stuff. But stroking, oral, a little slap and tickle, grinding, humping, jerking a man off with my nylon feet, all of that sort of thing.
At the beginning I told Tony that if the relationship felt right to us then he would be my first. That thought excited him and myself, as well. So, eventually we had that discussion, blushing throughout. He promised me a wonderful night and he delivered with a nice evening downtown, some drinks and then a room at one of the better hotels.
I never go out dressed in public. I’m too worried I’d be recognized. That’s not to say I wouldn’t do it in another city. I’m sure it’d be thrilling. I’d be a nervous wreck. Yes, all those men turning their heads, ogling me. Oh my.
Other men. That’s where I’m going with this story. Put two and two together with what I’ve said so far. Tony owns my ass and I thrill at the thought of other men desiring me.
Yes, I also told Tony that one day he could be sharing me, kind of like his hot wife. He was way into that possibility, another criteria for choosing Tony.
We’d roleplay that sort of thing from time to time and after he claimed me and began to fuck me regularly we began to talk about it really happening. He wanted to make sure I was broken in.
Tony has a couple of guy friends, Bill and Tom, whom he’d talked about on occasion. One night while they were all out drinking and the conversation had turned lewd he spilled the beans about me. I guess they were quite surprised. Tony immediately regretted telling them but they reassured him of their discretion and trust.
Tony told me that they showed no real interest in it, like, hey, it’s your thing, go for it. But as the weeks went by and they’d get together the subject of me would come up.
Both of them are married, as well. And ısparta escort with many men of similar age the sex life at home is lacking a bit. They admitted that, though, they’d never really considered finding a crossdresser there was an appeal to it. It didn’t feel like cheating, exactly, and there isn’t that messy fear of falling for another woman or her falling for them. Kind of the best of both worlds, Tony told them. Dresses like a lady, can sort of look like a lady, but has that male libido which makes the lady a tramp.
He did tell them if they played their cards right they might one day meet me, and more. Tony would take discrete headless photos of me sometimes and he showed a few of them to the guys. After that it was a bit more persistent, almost pestering him to set something up.
One night sharing a beer at a brewery he asked if I was ready for that next step. In fact, Tony put it this way. Well, is Julie ready to be my slut, my call girl, my whore, my hot wife. I swear there was a twinkle in his eyes as he grinned mischievously.
I’d seen photos of Bill and Tom, and while I didn’t find them as attractive as Tony, they seemed like nice guys. Tony promised me they’d be gentlemen and that he’d protect me should things get out of hand. But, he added, like me, they know what they want. He grinned and winked.
I told him I was as ready as I’ll ever be so let’s do it. I’d fantasized about this for decades, literally. Of course, I was ready.
He booked a suite for a Friday at the same hotel where I’d lost my virginity. There was a ballgame that night which gave good cover for all of us.
Tony and I drove down to the hotel together that afternoon. That’s the thing, Tony was a friend so it wasn’t peculiar or a problem to go out with him. Two normal guys going to a ball game.
Truthfully, though, I didn’t have to worry about being caught by my wife. She has known that I crossdress since before we got married. I made sure of that. Second marriage and I wasn’t going to have to hide anything again.
She also knows that I see other men and she also knows that I’m cautious and particular. She knows of the trouble I’ve had in finding Mr. Right and she’s happy for me. She would even like to see me get fucked by Tony. I’m sure that’ll be on the agenda soon. But all my other friends don’t have a clue and I want to keep it that way.
Tony, on the other hand, has to be doubly discrete. What with his wife and work, and friends…well, except for Bill and Tom.
So we get to the hotel and I’ve brought an overnight bag. I wait in the wings for Tony to check in and feel especially in character, you know, those dynamics I talked about earlier.
We go to the suite which has a sitting room and the bedroom.
I lay out my outfit for later on the bed, a bit of teasing for Tony and myself. Tony tries to get frisky with me but we both know that cumming will put quite a damper on the proceedings that are soon to take place.
In the elevator I hold out my hand to show that it’s trembling. I’m that nervous. Tony takes hold of it and calms me down.
As the doors open we break free our hands and head outside and down the block to the bar where we’d planned to meet the men.
45 minutes gives me a good head start to acquire some liquid courage and I order a gin and tonic. Into the second gin and tonic Tony, facing the entrance spots them and waves them over. My heartbeat rises to my throat.
They couldn’t kadirli escort be more gentlemanly, though, as we all introduce ourselves with knowing smiles, like a secret club. They’re actually as nervous as me, and Tony, the confident man he is, tries to ease our minds.
The conversation is good and not at all sexual with talk about some of my favorite topics, music, sports and the city we all call home.
Near the end of my fourth drinks, Tom and Bill’s second Tony jokingly says, well, we all know why we’re here. I immediately turn red as Bill and Tom grin. Tony suggests that I head down to the hotel and get ready, that he’s very anxious for his friends to meet Julie. We’ll all have another drink and be up to the room in 45 minutes. I agree, smiling meekly, standing and saying goodbye.
I feel out of body as I walk to the door, my hips intentionally sway in the tight jeans as I feel all of their eyes on me.
It feels as if I float down to the hotel, a bit buzzed and my mind whirling.
Up in the room, I undress and take a short but soothingly warm shower. I towel off and realize I haven’t put any music on so I find some smooth jazz and begin to apply my makeup, then tease my hair with the blow dryer, finally spritzing myself with high quality perfume.
I’ve chosen a rather kinky outfit that includes both pantyhose and stockings. First slipping on a pair of black lace French cut panties, then carefully tugging on sheer light black pantyhose. Next I put on a tight back lace top followed by a black lace garter belt and sitting on the bed roll on a pair darker black stockings with lacy tops, attaching them to the garter belt. I step into a tight black faux leather skirt that rides mid-thigh, exposing the lace stocking tops. A ruby red silk blouse is next and, finally, I slip into a pair of four inch black heels.
I don’t want their first impression to merely be Julie the slut but, rather, Julie the classy slut. LOL.
Now I begin to pace the room checking myself in the mirror over and over again, retrieving an airplane bottle of gin from the minibar. I finish that in two gulps and then have to adjust my red lipstick. And while I look closely into the mirror I make minor adjusts to the blue eyeshadow and mascara.
Then there’s the click of the door as Tony unlocks it with his card key. My heart leaps.
I stand in the bedroom, door closed, listening as the men enter and talk softly. Tony calls out for me, saying we’re ready and waiting.
I open the door and stand there momentarily as the music plays, the lights dim. I hear soft murmurs of approval from Bill and Tom as Tony walks to me and takes my hand walking me into the sitting room. And now, gentlemen, this is Julie. I smile, blushingly. As he raises my hand and twirls me around in a 360 to show the men his possession.
Both Tom and Bill verbally approve with compliments and even a whistle. Tony then walks me to them. Gentlemen, she is yours he states and gently pushes me to them. Tentatively hands reach out and begin to caress my trembling body. I look at Tony, my mind racing with emotions. He smiles and nods reassuringly and goes to make a drink.
Tom is the first to take his hand to my chin turning to kiss my lips. He then whispers how hot I look. Bill agrees and glides his hand along my firm backside. Damn, that is fine he says, now gripping a cheek gently. Feel that ass he suggests to Tom and now one hand from each cup my cheeks. kadıköy escort Made for fucking Tom grins wickedly.
Take off their shirts Julie, Tony directs as he sits with a drink in his hand. I fumble with Tom’s button down collared shirt removing it, as he stands bare chested. Not in fine physical form but not out of shape either. I move to Bill and unbutton a similar shirt as I feel Tom caress and grope. Removing Bill’s shirt I find a tanned nearly hairless chest and quite fit for a man around 60.
Now their pants baby, Tony orchestrates with words. I fumble with Tom’s belt, looking into his eyes. I undo the jeans and tug them down. He’s wearing boxers. I kneel in front of him and slip off his shoes and socks like a geisha girl. Then tugging off the jeans. There is a definite bulge even under loose fitting boxers.
I stay out on my knees and unbuckle Bill’s belt and undo his jeans, he’s wearing black boxer briefs, tighter so the bulge is more prominent. I do the same subservient gesture of removing his shoes and socks before taking his jeans off.
They both stand in underwear over me.
I reach a hand to press my palms to each bulge. I’m surprised when I feel the size of Tom hiding in the boxers so I wait and hook my fingers in the waistband of Bill’s briefs, tugging them down as his cock, about the size of mine, bounces forth. He has prominent tan lines which totally turns me on as I slip the briefs down and off. I reach and tug softly on his erection a few times before moving slightly to face Tom.
I just grab the legs of his boxers and pull, freeing a massive cock and I gasp. They all chuckle. Surprise, Tony laughs.
He must be nearly eight inches and very thick. I hurriedly help him step out of the boxers and then reach to take hold of what literally feels like holding a banana.
Oh my god I whisper. The first real words I’ve mustered.
Is it all you’ve dreamed of Julie, Tony asks me. I stammer with something about it all being so crazy and wild and finally I sigh, yes and take hold of each cock in each hand. Feeling their power, their heat, my power, my heat.
Start with Bill’s, Tom quietly suggests. You’ll need to get used to it he looks down at me smiling. I scoot turn slightly to Bill as Tom walks away to make a drink, his cock bounces freely as he walks, proud and naked. I look up at Bill sheepishly. Suck it Julie, he commands.
I lean in and open my red painted lips wrapping them around his head as he moans and I moan in harmony. My tongue moves along the underside as I suck him further in and he places his hands on his hips posing like Superman, tossing his head back. My head begins to bob.
I hold onto his hips and my thumbs run along his tan line at the waist. I suck and move my head. Bill’s hips now thrust as he begins to face fuck me. His hard cock going deeper and deeper into my mouth until I choke a bit, slobbering audibly on his pistoling shaft. I feel him place his hands on my head and then thrusts holding his cock down my throat as I moan again, my nose nearly touching his belly.
He pulls my head away as I gasp for air. Damn girl, you are a wonderful little cocksucker, Bill exclaims. Did you doubt me, Tony responds. I smile embarrassed, looking up at him as they talk about me as an object for their pleasure. Bill thrusts his cock back into my mouth as Tom sets down his drink and walks behind, crouching to caress my derrière through the faux leather skirt. He squeezes. Made for fucking, he comments to Tony. Tony grins and nods.
I feel a light smack and the crack of Tom’s palm on the material. Suck his cock, Julie, Tom commands urgently and then “crack”, another smack on my skirted ass. I moan around Bill’s cock, head bobbing and eyes slightly watering.
To be continued.