[MM] Jessi’s Debut

What I write below is a true story of my first time out as Jessi and everyone is at least 21, but most are much much older.

Understand while I would not call myself a prude, I have never been a slut. At 48 (basically married for 20 of them) I’ve had three female partners, one male one night stand, and one regular hook up. While I have done some wild things with some of them, bondage, blindfold, spanking, I’ve never really let go. With my regular hookup I’ve played around with Crossdressing. But never tried to be passable. But over the last six months I’ve fooled around with makeup, heels, nail polish, and a few nice outfits.

Last night changed all that. I knew there was a party Friday night at the Red Barn in Berlin New Jersey, and T-girls and CD got in free. So, I kept myself horny all week and decided I was going to drive the hour down there and let myself have some fun. I went to work in a red lace thong to keep myself horny all day. I came home from work and immediately showered and shaved. As I am doing this my regular hookup, who due to mutual scheduling issues, we haven’t met in over a year, called, and said he was free tonight. I told him I was getting ready for a party and would send him a picture as soon as I was ready and could head to his place first if he liked what he saw.

After I shaved, I painted my fingernails Torch Red, put on a coat of foundation as I have a 5 o’clock shadow as I shave, open the blush I just bought and apply it for the first time, then finish off with True Red lipstick. I put on my breast forms to go from a nothing to a solid C cup and try on some of the new lingerie that I ordered. None of the bras went well with the breast forms. So, I went with just my basic black bra. Then I added a thong that barely qualified as underwear, If it rode up at all my package would come free, and the back was no thicker then a shoe string. I put on a pair of fancy looking fishnets with built in garters, then put on my black leather mini skits and a shear cream top that only covers my belly if I hike the skirt up high, so I hike the skirt up and I am now almost ready. For shoes I decide to go all out and put on my knee-high black leather boots with 5-inch stiletto heels. To finish off the look I put on a dirty blond wig that goes down to the middle of my back and cascades down the sides of my face.

I take a selfie and send it to my friend he replies, “Fun party, I’d hit that” and with that I head out the door and drive over to his place. He lets me in we small talk a little he tells me to spin around so he can get a good look. I make one request of him I ask him not to make me cum, because the only way I will go to the party is if I am crazy horny, otherwise I know I will chicken out.

He says “You look amazing, it’s just a shame I will have to mess up that lipstick. ”

I laugh, “I have it in the car so I can touch it up.”

With that he pulls down his shorts and shows me his cock held out by a chrome cock ring. I drop to my knees right there and kiss the tip of his 6-inch circumcised cock. I lick my way around his head, then down and back up his shaft, then I take him all the way in as I deep throat him her tells me to look to the left, I comply and see that he is taking a video, so I look lustfully at the camera and make a show of bobbing up and down on his cock taking him all the way in each time. He pulls away and comes out with an audible pop. He orders me over to the couch where he sits down and I crawl between his legs and really go to town on his cock, eventually I focus on sucking on the head of his cock while jerking him off.

He moans, “oh you want to make me cum” I redouble my efforts stroking faster wanting my tasty reward. Soon he grunts and I feel him unload his seed in my mouth. I hold it there and when he tells me to stop, I pull off and show him my mouth and swallow. As I gently stroke him I notice a drop of cum on the tip of his cock and I lick it up.

I drive the hour to the Red Barn in Berlin New Jersey. I pull into the parking lot and find a space right up front. I am nervous as I said earlier, I am not a prude but have only every sucked two cocks, if I go in I know that number (among other things) will grow. I took a Viagra about 30 minutes before I got here, so that I am horny and worked up in an effort to get me to follow through. As I have never gone anywhere dressed like this before and I can only imagine what will happen if I let it.

About 10 minutes pass and I fix my lipstick, as I am doing this a gentleman in a car slowly drives by and waves, I wave back, as he drives by and leaves. I lock my phone and wallet in the car, taking only my ID, a credit card, and the fob to get back in my car. I take a deep breath and open the car door fixing my leather skirt and pulling down my top. I walk to the door my blond wig blowing gently in the crisp autumn breeze, which also send a cold jolt up my skirt. I reach the door and I open it and maybe a new phase of my life. I turn the corner into the store part of red barn and see 2 men and two beautiful women. As I start to head to the door for the booth and theater area the beautiful hosting in a stunning pink dress says, “You can go right in honey”. (since I was dressed as Jessie I get in free, SIS men have a $10 cover charge)

I do my best to raise the pitch of my voice and say a soft girly “thank you” as I open the door. As I have never been here before I don’t know what to expect layout or atmosphere wise. As I cross the threshold, I am stuck by how dark it is, and I am entering in the middle of a long hallway lined with booths. When the door behind me closes the only light is from the TVs in the few open booths.

I look to my right then my left and a man says, “hello beautiful”, and I am struck with terror. So, I dart into the booth right in front of me. I shut the door and notice it doesn’t latch. I am now wondering if he is going to come down and join me ignoring the one person per booth sign. I see the screen and there is a hot young white guy on his knees sucking a big brown cock. I start to watch, and my nerves start to calm. Then I see light as the door to the hallway opens, then shuts and I hear footsteps. This repeats three more times, the third time is just as the cut young man is open mouth tongue out waiting for his reward. I stand up and open the door to see a blond woman in a black dress walk down the hall to my left (The right from when I came in). I follow her and she makes a few turns. And we are greeting from the light of an 80+ inch TV showing straight porn to a room of several benches. I walk down the hall to see what the other small theaters look like and stop at the second one which is empty and showing gay porn, I feel several sets of eyes on me, but everyone keeps a distance.

I sit down on the bench and a towering man (I’m 6 ft 225, and he had to be at least 6ft 5) stands in the entrance way. I am siting very tight, legs shut, arms resting on my legs the only way I could look more nervous is if I was shaking. I focus on the small TV and notice the small low to the ground chair to the side of the TV. All the while keeping an eye on this man out of the corner of my eye. He wonders on to another area and a new man move into the edge of the room. I start to let myself relax. I move my arms to my side resting my right hand on the bench next to me and open my legs a little to seem more inviting. I start to alternate watching the TV and the 5ft 9 man in jeans and a dark tee-shirt inch a little closer and fully enter the room. He starts to fiddle around with his crotch, and I just stop the pretext of watching the TV and just watch him. He notices and pulls out 4 inches of hardening cock and turns towards me. He steps closer and closer, eventually I reach up with my hand and take a hold of his cock. As I stroke him, he fills out to a good 6 maybe 6.5 inches, and while staring at this stranger’s cock in my hand I say “I’ve never been to a place like this is it ok if I suck your cock”

He says, in a tone that can only be described as said with a soft smile. “You can do whatever you want sexy.”

I take that as an invitation and kneel in front of him and slowly take him in my mouth. Then lick all around his cock to make him nice and wet. He moans and I see movement out of the corner of my eye. To my left I now see a shorter man standing with his cock out, while he was a little shorter, 5.5 to 6 he was thick. I take the man who I am sucking deep and feel his short curly hair on my nose, and when I come up the other man has stepped closer. I do what comes naturally for a slut on her knees and I reach out with my free hand and start to stroke him. My fingers don’t touch my thumb.

As I am sucking the first man and stoking the second, I see a third man just behind them watching. The first man who I am know stroking and sucking, tells me to go ahead and try the other cock, I keep stroking him and turn my attention to the second cock, I lick the tip to get the precum that was forming, and I let out a moan. I open wide and take him all in in one shot, moving my hands to play with his balls. He lets out an excited grunt and I touch my nose to his belly and hold myself there sucking till I gag. I then took turns sucking each of them. The first guy eventually pulled away and left I quickly focused on the second guy and noticed a new cock right near my face, so I took him in hand and stroked him while going to town on the second guy. He either came very little or leaked a lot of precum in my mouth and then zipped up and left.

So, I sat down in the little chair (my knees were hurting and focused on the third cock. He was longer he might have broken 7 inches, but he was nowhere near as thick. I took turns deep throating him to the point where I gaged and stroking him while sucking the top half of his cock. As I pull up for a quick breather, I notice a man standing by the wall with his cock out and another sitting on the bench naked stroking himself. I reach out for the new man standing next to me and stroke his 5-inch uncircumcised cock. While I do this the third cock pulls away and leaves the room, so I kneel in front of the fourth man and put my first uncircumcised cock in my mouth.

I had hoped he would grow larger, but he never did, though it made it easier to deep throat him. I suck on him like his cock is the only water source and I am dying of thirst. I massage his balls while I have all of him in my mouth. At this point I feel a cock poke my shoulder, the man from the bench is standing really close right now. I keep my focus on the cock in my mouth pulling the foreskin back and sucking on his head while squeezing and massaging his balls. I feel the other guy poke my cheek with his cock and as I do the uncircumcised cock let loose several warm jets of cum in my mouth, and I just swallow each one. As he pulls out the fifth cock pushes its way into my mouth.

I turn to give him a better angle with me now facing the bench, I see a naked man sitting on the bench with a dark figure between his legs. I don’t get much of a look at them as the fifth man guides my head with both hands to take his 6.5 in cock deep in my mouth. Since he is the first cock without an upward curve, he is able to push just a bit into my throat. I reach up with both hands and grab his ass, pulling him in deeper. I feel his head slide into my throat, and he lets go of his grip and moans. I keep him there for as long as I can, swallowing to tighten around his head. I pull up take a breath and go right back down. (I think this is why I had a sore throat the next morning.) I do this five or six times and I feel him start to pulse, I pull out and suck on just the head and I am treated to a few very thick spurts of cum. I collect them and swallow when he stops cumming and pulls away.

I see another man has sat down next to the naked man being sucked off. I crawl over between his legs and lick at his cock. He is long, I think he might be the third man with the 7-inch cock back for more or another man with a very similar cock. After a few licks as I am swirling my tongue around his cockhead, I hear “suck that cock bitch.” Not from the man I am licking, but from the other man on the bench being sucked.

Being a slut that has a hard time refusing commands I oblige and take his cock in my mouth and suck up and down about half his cock. He then says, “Take it all in! Deep throat that cock slut” I push my head down, so that I feel his ball on my chin and hold it there. “Oh, you really are a hungry cock slut aren’t you” I hear from the side commentator.

I pull off for a second and almost hiss “Yes” then go back and take him all the way in holding till I gag. I alternate between deep throating and sucking the top half of his cock. This continues for a few minutes and with a few small squirts he is done and pushes me off. I sit down on the bench to recover as it has been nonstop since I put my hand on that first cock.

The man being sucked off says, “slide over here sexy” and being the good little slut that I have become I comply without objection. Sliding over he tells me to watch the young man on his knees sucking his cock. He reaches around and pulls me close, so I am pressed up against him. I half expected him to kiss me. He then reached over and feels up my fake tit groping them and squeezing them. If they were real, I bet it would have hurt. “Climb up on the bench so you can get a better look” I comply as if in a trance and while I am kneeling on the bench, he lifts up my skirt and says, “What slutty panties you are wearing.” Then he proceeds to treat my ass the same way he did my breasts. Squeezing and fondling it with a very firm touch. I moan and the man sucking his cock I guess had enough of sharing this man’s attention, so he gets up and quickly leaves.

“His loss your gain girl, get down there and suck me” he orders. I am tired, my mouth and knees are sore, but I can’t help myself I get down between his legs and take him in my mouth. I suck him for a few minutes, and he pulls out and rubs his wet cock all over my face. “Climb up here and suck me some more” I climb on the bench on all fours and take his cock head in my mouth and stroke him with a free hand. “Lay down” he commands, and I do, keeping his cock in my mouth the whole time. While I am laying down, he pulls up my skirt, exposing my shoestring black thong and exposes my pale white cheeks. I think I am glad I didn’t wear a temporary tattoo. He gropes me roughly and lands a single spank causing me to moan with him in my throat. “Maybe I should fuck you, I bet you would like that?” he says rubbing my wig and holding me down so I can’t say no.

I mumble with a mouth full of cock “Mo.”

He keeps groping me and says, “Maybe I’ll just rip the skirt off, climb on top of you and rape you? You’ll like it when I’m in you?” I start sucking harder and stroking his cock hoping to finish him quickly and head home. “Oh you want me to cum do you, do you want it in your ass?”

I say “Please no” and when he asks where do I want it I say “My mouth”

“On your knees slut, I will give you want you want.” He tells me sounding a bit disappointed that I didn’t offer my ass and I move back between his legs. I go to suck him, but instead of letting me take his cock in my mouth he slaps my face with it. He does this while stoking himself and slapping my mouth, cheeks, nose, forehead, glasses. And after a rough few minutes of this he barks “Open up.” I comply and stick my tongue out. He points his cock at my mouth and when I feel the first blast hit my tongue and upper lip, I take his head in and suck. He nearly fills my mouth; I swallow as he now looks asleep on the bench. I stand up, straighten up my clothes and make my way out to my car and then to home. In just over an hour I at least tripled my lifetime cock count, what a night.

As I type this there is another party this Friday. Do I go? Do I give up my ass? Do I let myself be spit roasted?

Let me know what you think. If ten people tell me to go I will, if 15 say and get fucked who am I to argue, and 20 what me spit roasted who am I to argue. If 40 people comment, I wont say no to anything that night…

Source: reddit.com/r/gonewildstories/comments/rfwfen/mm_jessis_debut