Sissy Pantyhose Stories: A Collection of Fascinating Tales

Sissy Pantyhose Stories: A Collection of Fascinating Tales

A SPECIAL NIGHT, LACI’S FIRST…

Prologue:

My name is Lawrence, I’m a young 40 something widowed white male, living a heterosexual life. However I have my feminine side, her name is Laci and as such I am a transvestite. I have preferred the long classical term of transvestite for a genetic male who dresses in women’s clothes. But crossdresser also works as well.

As a transvestite in my full on Laci mode I have found that I have bisexual feelings and thoughts. It’s odd as a typical dude, living mostly as a guy I have zero interest in sexual desires with men. Being widowed with a 20 something daughter who is A’Ok with my Laci side I have been sexual with genetic females such as my now late wife.

As a transvestite I’m a what you would call sexually virgin with men. Nerves have held me back as such but since my wife’s passing due to a car crash I have been coming more and more out as Laci, including going out and about, in recent times going to clubs with a few genetic girl friends who work at the office in the company I work at has really allowed Laci the sensuous and quite cute crossdresser to begin to bloom.

Yes, some office girls know about Laci and we’ve gone out a few times. I’m the eldest of the group as most are in their late 20’s or early 30’s but they love seeing the working dude Lawrence transform into feminine, sexy and cute Laci as we tend to socialize.

So this written story is an account of a night out as Laci with a few office girls. It’s a Saturday night, and I’m showered and getting ready as Laci. The office girls who will be going out with me are Tammi (33 years old), Jenny (29 years old) and Katie (28 years old) They will be by to pick me up whom I will be done up as Laci… So onto the account of this night.

The Story of a Special Night, Laci’s First Rendezvous.

I’m in a bit of a rush now having showered and given myself a wonderful lotion rub down as I am getting into my girlie mode. I just love dressing up as cute and sexy Laci. I’m a bit behind as the girls will be by at 7:30pm to pick me up tonight, so I rush a bit to get ready.

The plan for us is to go out for a fun ladies night dinner as a place called ‘Sammy’s Bistro’ a conventional but classy restaurant, then we will go to a very cosmopolitan night club called ‘The Edge.’ It’s open minded for any and all to come. So it’s not uncommon to find transsexuals, drag queens and transvestites there along with gay couples and groups, but its also a popular club for straight, bisexual couples and singles.

I’m now dressed in my black high cut lightly padded to help give me some curves silky panty and matching black silky bra. My modest, high quality but perky breast forms are in my bra give me a modest B cup look. I sit at my makeup mirror and put on my face so that Laci can rock it tonight. Concealer, foundation, setting powder help to smooth out and make feminine my face.

It’s a good thing for crossdressers to get the foundation on well and do some hi-lights and contouring to feminize her face. Smokey eyes will be my look with gray to smoke with light and darker purple colours to make my green eyes pop. Rimming my eyes with kohl eyeliner and shaping my kept rather androgynous eye brows with dark brown pencil and powder to get a more open eyes and girlie look in brows. I use a light purple/pink blush to hi-lite my cute cheeks.

My lips are drawn in blood red lip colour for a touch of fierceness. Light powder to smooth my look and then spritz of Chanel No. 5 perfume which was my mother’s favourite perfume so it’s an emotional fragrance for me as a girl and with that I am done with my makeup.

Laci is a lucky transvestite as she looks very cute and generally passable, but as Laci I am very feminine in mannerisms and have found that I’m treated as I present, a female. I never forget that gift by God to look to be girlie looking in my face and my tall 5’11” normal to slender body with killer gams.

I look in my full length mirror and say, “Damn girl you are so blessed to have killer and rather long legs.”

I can pull off short skirts and dresses well. Pantyhose is also in my opinion a staple for finishing legs be you a real girl or a wannabe and play girl like me. Silky and sheer pantyhose make legs look sensuous and smooth to the eyes that will have the pleasure to see said legs.

My outfit for tonight is a white silky chemise with lace around the bodice. I white satin long sleeve blouse and on my legs black silky sheer pantyhose. Mmmm I’m looking good and sexy. My skirt is a black short but not a true mini skirt, short leather straight skirt. Stepping into it and pulling it up over my lightly padded pantied hips and booty is sensuously fun. Pulling up the back zipper is a reminded that I’m wearing cute women’s clothing.

I sit back down and apply blood red coloured artificial nails in a gently long but not too long style to my fingers. I have to use my fingers for my work so as such are not suited to grow out nails. I put on a pair of silver dangling multi hooped earrings, a cute silver boxed cut heavy style necklace, a ladies silver bracelet watch. My wig tonight is my blonde with light auburn hi-lites just past shoulder length with cute bangs and a wispy style wig to it. It frames my made up face so sexy and cute.

Looking up I see it’s 7:21pm. The gals will be here soon. I grab a cropped black faux fur jacket and pull out my Pleaser brand black over the knee boots. 4 inch cute spiky heels look sexy and fun but will allow me to be all night long in heels. As I zip up each boot over my feet and legs I tell myself how much I love heels and over the knee boots.

The doorbell rings I grab my black over the shoulder purse filled with my ID. phone and cash inside. I scamper down stairs my heels click on the hardwood floors of my foyer as I then open the front door.

Tammi smiling says, “Hey girl, you ready for a fun ladies night out?”

I reply, “Yeah I am, come on in for a moment gals.”

As Tammi, Jenny and Katie enter we all greet each other with girlie kisses. Tammi is dressed in a black shirt dress just above her knees with black pantyhose and black suede 4 inch spiky high heeled knee boots on. Her jacket is a pink denim jacket,

Jenny has a pink satin blouse on a black knee length straight skirt, black pantyhose and shoes are black 4 inch spike heeled pumps. She has a white shawl on as well.

Katie is in a gold satin blouse, black denim mini-skirt, black back seam pantyhose and 5 inch black patten spike strappy pumps. Her jacket is a black leather biker style cut.

All the gals are made up and perfumed up for a fun girl night out.

I grab my keys and we all step out of the house as I close my front door. We all click clocking down my walkway in high heels as we walk to Tammi’s Jeep Grand Cherokee and like proper ladies we each all step up inside the Jeep. The smell of perfume permeates. I sit in the second row of seats with Katie and Jenny sits up front with Tammi driving. The look of us all is so feminine, sexy and girlie… I love it so much as a transvestite as I can just let my life’s stresses flow away as I take on the roll of Laci, a cute, sexy and passable transvestite.

The drive to the restaurant is normal and about 10 minutes in length. The chit chat is very girly and yes myself as Laci carries on quite well with girly chat. We talk about each others outfits, fashion in general a bit of news events and talk about guys.

The girls are hoping for some fun times and maybe connections with men. Discussion about such involves me as my coworker girl friends know of my growing desires since my wife’s passing and growing acceptance as a transvestite that I have some bi-sexual desires. They know these feelings only come with me in girlie, Laci mode. Bi-sexualism is an a’ok thing to talk about.

The girls know I am a virgin with any sexuality with men. Of course I’m nervous but I feel so sexy and cute and we all talk about maybe a hook up and especially for me. It’s all quite intoxicating, yet the male in me is a bit funny about it. But Laci is dressed to thrill and well after a few previous nights out over the last many months where no hook up was made, maybe tonight will be different.

Arriving at Sammy’s Bistro us girls step out of Tammi’s Grand Cherokee, heels clicking, the girlie chatter cracks the air. Click clock the sound of high heels enter the front entrance of the bistro. We are met by Jack one of the front of the house staff, telling him of our reservations Jack walks us gals to our table. I’m so enjoying this moment. Yes, all the girls are enjoying things but somehow being a part time girl in my crossdressing I soak it all up even more.

Seated we begin to look through our menus as our waitress Tiffany addresses us, “So how are you ladies tonight?”

We all reply, “Good.”

Tiffany compliments us on our outfits and asks what are our plans tonight. We tell her that after dinner we are going to have a fun time at ‘The Edge’ night cub. She smiles and notes that she and her friends enjoy ‘The Edge’ as well.

Taking our orders she gathers our menus and walks away.

For the rest of our time at Sammy’s it’s more girl chat, it feels so good for me to just relax and be with some positive, lady coworkers and friends. Of course during our meals we all do the girlie thing of going to the ladies room to primp and preen. Being a respectful and endeavoring to pass and act like a girl there is no issues with me in the ladies room. It’s not my intention to be some crude, look at me I’m a bloke in a dress and pervert to gain access to a ladies room. I’m carrying on like a confident, cute and sexy girl.

As dinner wraps up we all get our jackets or shawls on, grab our handbags and it’s off to ‘The Edge.’ Looking at my silver bracelet watch I see its about 8:45pm so the night is still pretty young. Each of us touch up our perfume in the Grand Cherokee as we get to the night club and soon we are parked and again four, sexy, cute and playful chicks step out and plant our high heels on the asphalt.

It’s cool and dry tonight with just a wistful cooling breeze which flows up our skirts or dresses. For me it’s an electrifying feeling walking outside with a short skirt, sexy black pantyhose and high heel over the knee boots on.

As we enter the club, music is playing for those who want to dance. It’s a fairly busy place on weekends and this Saturday night is no exceptions. As I noted earlier ‘The Edge’ is a cosmopolitan club, you find straight and gay singles, couples, groups including not uncommon to see transsexuals, drag queens and transvestites like me so it’s a fun and comfortable place to be at.

The brawny door man greets us as we enter and gives and ok or not on the dress code. Of course we know from being here before what to dress like and our door man who’s name is Greg a big 6’5″ 265lb. former football player treats all of us as the cute ladies we are.

We decide to find a table not to close to the dance floor so that we can talk, relax, scan the crows and yes maybe flirt and prowl for some fun. For me this as a chick is still kind of new but each time I come out to ‘The Edge’ with the girls I get a bit more confident and braver. I learn cues genetic girls have to be better prepared for night club fun.

I’m not the only dude in a dress here tonight. We notice at a far booth a few drag queens who are here and look to be finished a show at maybe one of the true gay bars in town and they are well being naughty with a couple of men. Tammi notices a popular Youtuber trans gal in another booth with her boyfriend. On the dance floor is a mix of straight couples, a girl like me, a transvestite dancing with a guy and a couple of leather men gays doing their stuff. As I said it’s a cosmopolitan club.

We all order drinks, Tammi being the designated driver is ordering her drinks virgin style. We all chat on all sorts of topics, from current news, to fashion and makeup and me as Laci being with three lovely young genetic girls the talk gets to men. It’s incredible to be able to as do this Laci as in my male mode Lawrence much of this discussion would not happen. In male mode with others notably blokes it’s more sports, politics, cars and yes chicks talk, to which in my male mode I’m perfectly good with. As Laci who is say a feminine escape for me in her persona girlie talk is so much fun.

Soon guys do come around and ask the girls to dance. At first they say no as we all have only been here for a short while, but they invite the men to call on them after the girls had some time to soak up the mood of the club.

Katie soon notices a gent who seems to be eyeing me. My drink in hand straw pressed to my blood red coloured lips I casually look to where she tells me he is. He is standing at the bar leaning back on it a beer in hand as if he is scanning the crowd. He is about 30 feet away. As I sip my drink I look at him.

Katie asks, “Well Laci what do ya think?”

He’s easily 6’2″ or more and oh maybe 200-210lbs, maybe late 40s so a bit more mature than me. He has clean cute light brown hair and is wearing a black button shirt, under a black leather biker style jacker, faded blue jeans, looks to be in a pair of Daytons.

I reply a bit sheepishly, “Na… he can’t be lookin at me.” I add, “Yes he looks cute.” I pause giggle as it’s kinda strange for me to talk like that about another man for in my male mode it would be of little interest, but a cute and sexy Laci I am in girlie mode.

Jenny leans in giggles and says, “Hun he is lookin at you, trust us GG’s we know what and when men look at us chicks.” she puts her arm around my shoulder sips her drink and adds, ” Laci this is still new for you hun but it’s time to accept, you look cute and sexy enough that men will see and look at you, by the way babe, mostly straight men or ones who swing both ways who like trannys and crossdressers.”

Tammi adds, “Girl flirt with him, see how he responds.” she pauses and see’s I’m a bit nervous, “Come on Laci, look right at him with your sexy made up eyes, smile and put that red straw to those hot lips and sip your drink, keeping your eyes on him.”

So I do that and its electrifying… He responds with a light smile and he casually raises his bottle of beer at me.

Katie says, “Yep he’s on to you Laci. It will be interesting if it’s just simple looking at you as eye candy or maybe more.”

We all carry one for a few more minutes and then Jenny takes control stands on her heels and grabs my wrist bringing me up on my heels.

She says, “Come on, come with me to the little girls room, you will be passing near by him as you do so, dammit girl you take your sexy made up eyes and look at him with a flirt as we walk by.”

I choke up and say, “No.. I can’t do that.”

Jenny adds, “Hell ya you can, you want to live like a cute, desirable chick tonight, well you are here dressed as Laci, Lawrence the dude in you is back at your home. It’s Laci’s time girl.”

We both then walk towards the ladies room, my heart is pounding and I can feel it and hear it even over the music playing in background. As my heels click with each step a part of me wants to run away, another wants to play and see what happens with this man.

As we both walk past him, Jenny whispers, “Look over your shoulder and right at him Laci, smiling too.”

As if under her command I do that and observe him look right back at me, him scanning me from head to toe and back up again as he smiles back at me. My heart feels as it’s going to jump out of my throat as we enter the ladies room. I make my way to the counter put my hands on it to keep me from passing out. I looking in the mirror see Jenny looking back at me in the mirror, a couple of other ladies are just leaving.

She says, “Well hun welcome to the world in which us GG’s live, kinda scary huh?”

I looking at her reflection say, “Oh Hell ya, remember I’m still a dude, this is as a full on girl out clubbing is still kinda new to me.”

Jenny reapplying her lipstick stares at me, stops and says, “NO! you are not a dude tonight, YOU! are LACI! a sexy, desirable chick. Lawrence is at home watching a movie, or something got it?”

I stare at my reflection and I see a cute, young 40 something lady staring back at me, I say, “God you are right but I’m so nervous.”

She is putting her lipstick back in her purse and is proceeding to a stall to pee says.

“Hun I gotta use the loo, you relax, fix your hair or makeup, being cute and feminine is what men look for, ok?”

I say, “Yes Jenny you are right.” I move to use a loo too.

As we are done and back to preening in the mirror some other girls come in including the popular Youtuber trans girl. Jenny asks her what she thinks about my look? To which the trans girl reply was I got it as a hot little crossdressing gal, so flaunt it.

Jenny, says. “Laci, I think I should walk out a few moments ahead of you, that way you will pass the guy on your own and well who knows? Huh?”

I reply, “Yeah, I guess so, but I’m still nervous, this is all sorta new to me, but well, yeah.”

The trans youtuber is now preening in the mirror and she stops, turns and says, “It’s Laci? Right? Can’t help but hear you all talking. Hun you looking to hook up with a dude?”

I look towards her and reply, “Well yeah I guess, it’s been something I have thought about often since I came out as a transvestite, but well I’ve never done it before.”

She smiles and says, “Hun if this is a desire of yours to be swooned off your heels by a dude you fancy.” she scans me from top to bottom, “Girl you got it, you look divine, have fun, when I decided I was trans I knew for me that I would want to follow desires I had for good men and well Laci I love it, so just go for it, strut in those heels and see where it goes.”

I smile and reply, “Yes, thanks for your moral support.”

She walks out and Jenny also begins to walk out looking back, saying,”Girl, you want a chance to see if this guy is interested in you, then well girl you know what to do.”

I look into the mirror, check my hair and say to myself, “Laci you have wondered what it would be like to have a man interested in you, well Darlin this guy could be it.”

I then walk to and open the ladies room door and step out into the hallway. The guy has moved near by where it will be hard to pass without some possible interaction. So I swallow hard and begin to walk down the hallway. I glance up to the guy and he looks and smiles.

As I am about to walk past him he says, “Well hello beautiful.”

I stop look at him, smile and reply, “Hi, well thank you.”

He replies, “I have noticed you and girl you look great, I see you are here with some girl friends.”

I say, “Yes, some ladies that work in the office for the company I work for. I have a good time of being girlie with them.

He says, “I love your boots, always love gals in over the knee boots and you make up very cute as a girl.”

I blush and reply, “Well thank you.”

He moves closer to me, leans a shoulder against a wall and fidgets with his finger and says, “My name is Johnathon. What is yours?”

I stand facing him reply, “My name is Laci, it’s nice to meet you Johnathon.”

He smiles and says, “Beautiful name, Laci. Would you and your friends like me to buy you all a drink?”

I reply, “Well, I guess that would be nice.”

We begin to walk back to the table where my girl friends are and as I sit down Johnathon introduces himself and they to him. He says to them he wishes to buy all of us a drink and we all give him our order. He walks away to the bar to tend to this.

Tammi says, “Well Laci, you have a real man interested in you, feels good huh?”

I smile and say, “Well yeah but it’s still so odd for me but yeah Tammi it’s kinda fun.”

Katie adds, “Well Johnathon is definitely a hunk, heres to you maybe having a good time with him.” As she then finishes her drink.

Jonathon comes back and tells us the waitress will have our drinks soon. He asks if he can sit with us and we all agree as he sits right beside me. The girls do what girls do, grill him, politely and they know to kinda big sister look out for me as being on the feminine side of a possible hook up with a dude, they know to watch out for me.

Johnathon tells them that he’s a regular dude and enjoys all ladies but has a hankering for trans type gals and crossdressers like me. Drinking up the chat is all about us, learning more about Johnathon and seeing how I feel. Johnathon invites me to dance with him and I agree as he takes my hand and helps me up on my heels. My mind is spinning with excitement and an odd new feeling. The booze I have consumed helps me get comfortable though.

The song is a standard dance song and the both of us dance typically and enjoyably. The other girls have also got on the dance floor too. They still watch out for me.

Johnathan leans close to me and speaking above the music he asks, “Laci would you like to well cut from this place and just go off together?”

I reply, “Well… ok, sure, but I want to touch base with my girl friends first.”

He says, “No problem babe.”

We walk back to our table and sit down, the others soon venture back too and I then say that Johnathon and I are going to get on our way. The girls are all happy for me but make sure to get some big sisterly stuff from Johnathon, his cell phone number and Katie snaps a pic of myself sitting with Johnathon.

He says he just wants to go to a quiet place with me to talk and feel things out. After my girl friends kind give me the all clear Johnathon helps me up on my heels and helps me on with my black faux fur cropped jacket. I grab my hand bag and say good night to the girls as Johnathon says good night as well.

As we walk out of the club together I’m very nervous but also so electrifyingly excited. This very exciting female like emotion is wonderful. Johnathon speaks softly as he tells me how gorgeous of a chick I make. I blush and thank him.

We get up to his car a silver Lexus GS400. He opens the passenger side door and helps me get in. I observe him walk to the driver’s side and I am lost in new emotions. As he gets in the driver’s side and starts the car he asks if he can kiss me, to which I agree and I get my first kiss as a girl by a real man. My mind is off in la la land for a moment. He says that he enjoyed the kiss and I agree.

We drive off and he says he likes a nice quiet coffee shop near by and I agree to go with him. For the next hour as we sit and have coffee, I enjoy talking with him and he does with me. He tells me he is a contractor and has been doing so for about 15 years. I tell hm about myself as Laci the transvestite and about my 21 year old daughter. I told him about my late wife’s passing due to a car crash about 2 years ago. I tell him I have always been a crossdresser and felt after my wife died that I had to really accept and enjoy my feminine side.

Johnathon tells me he is divorced with two sons one 25 the other 21. He tells me he is just a hetero dude who also has a thing for pretty crossdressers and trans girls. He says he has had a few hook ups and relations since his divorce 4 years ago.

We talk and talk some more getting to know each other but really building up comfort to what may end in some passionate excitement tonight. I am feeling very comfortable with Johnathon as he is with me. Our desires for more than just talk are building. I invite him to my place and he agrees. We walk to his Lexus and get in. The drive to my home is about 7-8 minutes away and we feel the growing heat and passion. I made it clear to him that he is the first man I have done this with and he comforts me with gentleman like words.

As we arrive and he parks in my driveway I find he scampers out to help me out of his car. As I stand on my heels, he makes an impulsive move and pulls me towards him, embracing me as he kisses me on my mouth and I am swooned, my right booted leg kicks up and backwards as sexual emotion rises.

Once he finishes he says, “Oh God, I’m sorry maybe I should not have done that.”

I am coming back down to earth in my mind and reply, “Um…n…no…um…no that… Oh God was great… don’t apologize Johnathon.” and now I lean towards him and plant another kiss on his lips as I impulsively slip him the tongue. My girlie dick is rock hard in my panty and I bet Johnathon’s cock is busting hard in his briefs.

We finish the kiss and he takes my right hand in his left as he walks up with me on my walkway and soon in my home. We get inside and he kicks off his Dayton’s but asks me to keep my boots on as they turn him on. I walk him to my living room and have him take a seat on the sofa as I ask if he’d like a coffee?

Once I have coffee made and then serve him we both sit down and drink as we sip our coffees. We small talk but we know what we really want. I am nervous but he is so gentle and comforting to me. I soon fall into his shoulder/chest area his right arm around me. His cologne and my perfume are permeating the air. I hear him breath and he pets my shoulder and kisses my hair.

My right hand on his lap and his left on mine between the top of boot and just below my skirt. He runs his fingers on my pantyhose. It feels so good.

I whisper, “Johnathon, I want to please you… I want to do it… I want to suck you off, I’m so turned on to want to do what a turned on gal wishes for a man she likes.”

He replies, “I do not want to force you Laci, but God yes, I’d love that.”

I then move from the sofa and onto my knees before Johnathon, looking into his eyes I can sense his burning desire for what is about to happen. As for me I am lost in my mind, Laci is about to have her first sexual rendezvous as a transvestite and I am so turned by it. My late wife gave me blow jobs as me being her husband Lawrence, but as a girl I so want to do this to a man.

I begin to undo his belt and then I pop the fly and pull the zipper down to his jeans. He helps me with pulling his jeans down, I get them right to his ankles. His cock is like a tent pole is his black stylish briefs. My blood red finger nailed fingers now pull his briefs down and out pops his nicely large but not massive white cut cock. I get his briefs to his ankles as he leans back in my sofa and his eyes like laser beams stay fixed on me and my sexy made up face.

My mind wanders for a moment as I stare at his hard manhood. Lawrence would never do this but for so long Laci has wondered and dream’t about doing this. I’m on my knees and I look up at him, doey eyed and he smiles and I smile back as I then slowly move my head to his cock. I open my blood red lipstick coloured lips and his nicely bulbous cock’s head enters my mouth. I hear him sigh and moan as he sees his cock slip away inside my girlie mouth. My lips keep a pleasurable seal as my tongue begins to dance with his erect cock.

Johnathon sighs and moans as he whispers my name, “Laci…Laci…Laci… Oh God… Laci.”

This turns me so on and I slobber more on his cock. I suck away and play with his cock with my tongue. I begin getting very intense in my mouth work, my head bobs, my hair swings back and forth. Johnathon can’t help but to take his hands and pets my hair. His moans and sighs go on and on.

He begins to talk a bit dirty to me, “Oh God Laci you little tart, you are a sweet little cocking bitch… Oh God I love it you little bitch…”

I myself on my knees before this man love it all. I love his mildly dirty talk to me and his nice girthy cock dancing in my mouth. My slobber gets the better of me and some saliva streams from my mouth and onto the sofa as I take his cock more and more intensely with my mouth, my head bobbing back and forth.

Johnathon is near lost in his mind I peek up and see his head knocked back over the sofa back side as he moans and groans. I can sense he is getting close to ejaculating. GOD I WANT IT SO FUCKING BAD!! I want to taste a mans cum, I want to swallow it. I work on his cock with full intention, his hands now begin to press on the back of my head, as he helps work me on his cock harder and deeper.

His moans reach a zeal of utter passionate lust, his seminal fluid has worked its way through his cock and as he lets out grunt and a moan his cock ejaculates a massive load of gloriously hot and gooey cum right into my mouth. Oh God he lets a thick and rich volley of cum go so intently in my mouth. He shoots out volley after volley as I fight to swallow it all. He sighs and moans as he soon is spent. I pull off his cock, it smeared with my lipstick and he pets me as I look up.

He says, “God that was great Laci, I loved it so much.”

I smiled all finished swallowing and reply, “Johnathon, I loved it, I so enjoyed making you happy. I loved being a girl and pleasing you to orgasm.”

I then got back up and sat beside Johnathon on the sofa. He pulled his briefs and jeans back up but left his fly open. He pulled me close to him again with his right arm around my shoulders. He repeated how much he enjoyed the blow job. I told him it was a wonderful thing for me to do and that I enjoyed swallowing his hot cum.

We then just sat quiet for a few minutes where then I offered him another coffee and then got up and walked in my heels to the kitchen to get the coffee. But I first go to my bathroom to freshen up a bit. Fixed my lipstick touched up my face powder and decide to take some anal lube and fingered my bottom as I am pretty sure Johnathon will be taking my anal cherry tonight and I want to be ready for it.

Coming back a couple minutes later I served him the coffee, to which he took a sip and asked for me to put on some music. I walked to the hi-fi and tuned to a classic rock/pop FM station. It was at a pleasant volume as I stood up tall in my over the knee boots, black short skirt, white satin blouse and of course black sheer pantyhose.

Johnathon pipes up, “Why don’t you do a sensual dance for me? I’d love to see you gently but sensuously dance and run your hands over your tall, thin body Laci.”

I smile and noted to myself the music, as the radio had Santana, Black Magic Woman playing and I tried to sensuously sway and dance to it. My hips swaying and hands running over my body, my hair swaying around as I strut in my 4 inch spiky heels.

I see Johnathon enjoying the view, his right hand begins to move over his crotch, jeans fly still popped open. I swayed and strutted more and more sexy to the music, enjoying watching him get turned on. As he felt his growing erection still in his briefs I strutted out of eye sight into the kitchen and the peeked back my hair over my face as I showed my head from the opening between the kitchen and living room.

I see that he likes this. I pout my red lips and take my index finger with its red nail, kiss it with my lips and point the finger to Johnathon. He is continuing fondling his erection still inside his briefs.

I strut in my heels back to him, lean over and my hands run up his thighs and over his hand which is playing with his cock. I shake my head left and right sensuously and then go in for a kiss, planting my lips on him slipping him my tongue. The heat of new passion builds more and more as the Santana song ends and the next song flows over the speakers. Sade, “I Gave You Love” is the song and that does it. Johnathon gets up from the sofa his pants barely held up as his hands grasp my hips and he pulls me tight to give me a hard kiss.

Sade playing that song has him so want to deflower me anally and I so want him to do so. He directs me with passionate authority to my dining room table, in dim light and I bend over, strutting in my heels, I with Johnathon’s help adjust my backside in a graceful bend to allow him to hike up my black skirt and then he takes has hands and eases down my pantyhose and panty, my smooth white bottom is waiting for him to take his prize.

I lean over the table and arch my back up as I begin to beg Johnathon to take me. I tell him the song is so right for this moment. His pants drop to his ankles as he then eases his black briefs down as well. His nicely endowed hard cock is like a one eyed monster on the prowl for some tail.

I say “Oh Johnathon, I so want you but please go easy it’s my first time.”

Johnathon in deep breaths leans over my back, brushes my hair from my neck and kisses my neck then says, “Oh babe no worry I’ll be a gentleman and I so want you to remember this night forever.”

I moan. “Mmmm can hardly wait.”

His firm hands kneed my butt cheeks as he opens me up and begins to gracefully insert his stiff cock. I whimper and moan a bit and he slows, nice and easy. I thank him for being so gentle. He prods and begins to work it past my lubed sphincter. Once past it the arousal for both of us is high. My girlie dick is also rock hard.

Sade’s song ends as Johnathon gently begins a rhythmic method to his penetration of my backside. I sigh and moan, my hands fidget on the table top. What a sight I must be from Johnathon’s manly, dominating position.

The disc jockey in a gentle almost smoker’s sounding voice speaks words of love and lust for his listeners hoping that many are enjoying wonderful times with a lover of their choice tonight. I hear it and my mind tells me yes, I’m enjoying my night with Johnathon. The disc jockey cues up Foreigner’s, “Waiting For a Girl Like You.” another OH MY GOD song for me and Johnathon.

Johnathon is now in a good and growing forceful rhythm of penetration. I’m balancing between twinges of pain and ecstasy as he fills my backside, rhythmically penetrating me.

He leans forward as he thrusts back and forth, his right hand reaches under my abdomen and he grasps my rock hard girlie dick. Instantly I feel it and my dick grows a maximum hard on as I moan to this grasping.

He says, “Laci, I want so bad to have us cum together or as close as we can, let me stroke your girlie clit and lets try to cum together.”

I chime in with my moans, “Oh…yes…oh my God…J..Johnathon, yes, I love that. God stroke me as you take me… Ohhh!”

The two of us work as if we are now one. His nicely endowed manhood is taking my anal cherry as he sighs and moans building up, ever more closer to cumming. Me, I’m near delirious my back arches as I take his manhood inside my bottom, my hands continue to rub over almost polish the table top in their fidgeting and his hand strokes my own hard girlie cock.

Foreigner continues to play and our collective heat of lustful passion reaches the climax as he grunts and groans and his cock shoots a good rounds and volley’s of cum up my backside. His hand stroking my cock and me feeling his cock shoot up hot cum inside me, gets me too now blow my load of girlie cum. Volley after volley it shoots and falls to my dining room laminate wood floor.

We are both enjoying mutually glorious orgasms and each volley of cum we ejaculate brings us slowly back down from our ecstasy. I feel my heart pound on the table top. Johnathon leans over and kisses my right ear telling me how much he loved this. I moan and tell him the same. He eases his now softening cock from my bottom and he steps back, reaches for his briefs, pulls them up and then does his jeans up. I reach for and pull my panty up, and then my pantyhose. As I get up on my heels a dollop of Johnathon’s cum spills from my butt hole and into the crotch of my panty.

We both make our way to the sofa telling each other how wonderful tonight was. Johnathon has me place each leg up on his lap for him to zip off my boots as he rubs my black sheer pantyhose covered feet into comfort.

We chat for a few minutes as he looks and sees that it’s almost 1:30 am and tells me he has to go. As we get up and walk to the front door, he puts his shoes back on and as the door opens we kiss, hug and tell each other it was so great. He agrees to call me later on today around lunch time time to talk about tonight. I tell him I would love that, we kiss once more and I tell him I’d love to go on a date with him again. He agrees as he walks to his car, gets in and drives off.

I ease back to my sofa, music still playing on the radio. I pick up my phone and see messages sent to me by Tammi, Jenny and Katie all curious of how things went. I smile and text each back with happy emojis and a brief message of how Jonathan was a man to me tonight and I as well as he loved it all.

Soon the girls began to message me back, each being happy for me and also telling me of how naughty I must have been to seduce my first man as the hottie I am named Laci.

I laughed to myself and sent back with texts saying I was a woman tonight and loved every minute of this total night, messaged them a good night and I retired for the night knowing sleep will be blissful and yes a part of me has changed, Laci is not just a girl, my feminine persona to my regular dude role of Lawrence, but she is now a sexually taken woman.

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Sissy tights
Sissy tights
1 month ago

Omg laci that was absolutely amazing that was one hot horny story, thank you so much for sharing,xx

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