A Boy Named Samantha

("A Boy Named Samantha" is yet another true episode in the sexual story of my life. I am purging my soul. Telling of my past "sins" is part of my repentance.")

I'm sure everyone who has attended a high school reunion has been shocked for one reason or another. Some people change dramatically and lives take directions no one ever would have predicted.

My five-year high reunion became quite the revelation. One of my best buds in high school made a stunning entrance in a black strapless, side-shirred and dramatically slit tulip-wrap dress. Sam looked gorgeous in that dress and much better than I ever could have. But his name wasn't Sam now; it was Samantha.

Where to start? Sam and I shared many interests back then, particularly computer stuff. I knew he liked boys better than girls, sexually speaking. Very pretty for a guy, he had a high pitched voice and the jocks teased him incessantly. I figured Sam would end up a priest, what with being Catholic and all. We lost touch in the years after we graduated. He ended up on the left coast and me on the east coast. Sam did visit me once in college and helped me reap revenge on those who initiated my brief career in the world’s oldest profession. But that’s a story for another day (Entitled “Revenge of the Coeds.”)

I’m standing at the bar at the reunion chatting with a couple old girlfriends when this what I thought to be a runway model approached me and asked if we could speak privately. I saw the nametag “Samantha Harrison.” The only Harrison at our school was Sam the dude. My initial reaction was that this was his wife, although I never figured Sam for the marrying kind.

A Holiday Inn hosted the reunion. I let Samantha lead me out of the banquet room and into the lobby. She dragged me onto the elevator and pushed the button for the fourth floor.

“I simply must talk to you privately,” Samantha insisted as we entered her room.

A bottle of Glenmorangie sat in the ice bucket just waiting to be opened. So I did. Glenmorangie, “Crafted by the 16 men of Tain,” the best selling Scotch Whiskey, at least in Scotland. I can’t believe I drank the whole thing. Well, most of it. Samantha had a couple shots. I needed something to dull my senses. Our conversation turned out to be more than I could handle sober.

“Deborah,” Samantha began, “I don’t know how to explain this to you. Maybe we’ll just play ‘show and tell.’ That way you will have no choice but to believe me.

I just nodded, having no idea what in the hell she might be talking about, but becoming incredibly curious.

“You know, Samantha,” I observed, “You remind me so much of the supermodel Frederique; about 5’11” and somewhat big-boned for a girl with large hands and feet and a deep voice. Frederique is a native of Holland but is now the quintessential New Yorker. She has done many ‘Cosmo’ covers, Victoria Secret catalogues, been on Letterman and Oprah, and my fav, the Howard Stern show. I just love it when the ladies, and it doesn’t happen often, hold their own with Howard and don’t just get giddy and nekkid. Frederique more than held her own.”

“You think I’m pretty then, Deborah?”

“Samantha, you are a total fox. Geez, I wish I looked like you.”

“Oh yeah, well I always thought you to be the best looking girl in our class and you still are, from what I saw of the other women at the reunion.”

“Say what, Samantha, you weren’t in my class. How could I ever forget you?”

“Yes, Deborah, I was.”

“I don’t understand, Samantha. Are you pulling my leg?”

“Nope, but if you pull my leg maybe you will understand.”

Samantha unclipped her tulip-wrap dress and fully exposed the lace-top thigh-highs. I noticed an unusual bulge in her stretch string thong. No, it wasn’t black; the color was “serpent purple.” I knew because I had the same thing in my lingerie drawer. At first I could only guess the bulge might be a Kotex maxi pad or some such thing.

Soon I discovered the reason for the bulge. Samantha pulled down her thong and revealed quite a nice looking large penis, about seven inches soft. I felt faint for a moment and simply could not speak.

When I caught my breath I didn’t know what to say so I began singing lyrics from “A Boy Named Sue” by Johnny Cash …

“Well, he must o’ thought that it was quite a joke. And it got a laugh from a lot of folk. It seems I had to fight my whole life through. Some gal would giggle and I’d get red And some guy’d laugh and I’d bust his head. I tell ya, life ain’t easy for a boy named Sue.”

“It’s real, Deborah. You can touch it if you like.”

I couldn’t resist. I touched it. Then I began to stroke it as it became erect and expanded to about ten inches. Obviously my overwhelming curiosity now demanded that I see “her” breasts.

“Please let me see your breasts, Samantha.”

Samantha pulled down the top of the strapless dress to reveal her beautiful melons; very full and firm and her nipples were quite erect, which I assumed my stroking her cock precipitated.

“I’m beginning to get the picture here, Samantha. You are Sam. And just how in the hell did that all happen?”

“Do you really want to know?”

“You are fucking right I want to know. This is incredible. Now tell me!”

“Would you suck my cock first? You are making me horny. Besides, I probably won’t have this cock much longer, if you get my drift.”

“Well, I never sucked a girl’s cock before. How come you never asked me to suck your cock when you were a dude?”

“Deborah, you knew me way back when. Just too damn shy I guess. Actually, a girl has never ever sucked my cock. Just guys.”

“You know, Samantha, this is a really nice cock. One of the best I’ve seen. Why would you want to part with it?” I began to nibble. “And it tastes good!”

“I want to be totally a woman and experience everything that a woman experiences. My doctor tells me that after the Sexual Reassignment Surgery it is quite possible I may be able to orgasm just like you do. I know that sounds incredible but that’s what the experts say. My doctor told me he will take sensitive tissue from my penis and use it to create my vagina and clitoris, which will hopefully provide a degree of erotic sensation. Exactly what degree of sensation, of course, won’t be known until some time after the operation. Some ‘new’ women have no capacity for orgasm and others get off big time. Here’s hoping!” Samantha gleamed as she downed a shot of the Glenmorangie.

“Now, you promise, Samantha, if I suck your cock you will tell me absolutely everything about this? I mean, you look so much like a woman, who would ever know. Well, except for this!” I deepthroated her cock. My pussy was becoming very moist because of this incredibly strange and erotic experience.

“Samantha,” I asked as I momentarily removed her cock from my mouth, “have you ever had sex with a woman?”

“No, and I don’t think I want to, at least not sexual intercourse.”

“But you have had anal intercourse with guys?”

“Yes, I have, Deborah.”

“OK, pretend I’m a guy and fuck me in the ass.”

“Huh?”

“You heard what I said. If you want to get off, fuck me in the ass.”

I laid face down on the bed and stuck my butt up in the air, and pulled up the bottom of my blue velvet slipdress. Samantha had an open invitation because there were no panties under the dress, just knee-high fishnets. The Analeze had already been applied liberally. I had to help Samantha find the right angle and eased her into me an inch at a time with one hand, playing with my clit with the other hand. If you can’t figure that one out, just let me inform you I have very long arms and I’m double-jointed. I can do some very weird things with my body.

Ten minutes later Samantha pulled out and shot hot cum all over my behind while I moaned in post orgasmic ecstasy due to the butt fucking and my own ministrations with my own fingers. Samantha had done it just right. Girls are so much gentler when they stick it up your ass.

“OK, Samantha, I got you off. Now tell me all the juicy details. How did you learn to act so much like a girl? Somebody taught you the ropes.”

“Hey, I read ‘Creating a Feminine Carriage: Figure, Posture, Walk, & Gesture’ by Elaine Sagant. She is image and movement consultant to the transgender community. Everything from bending and reaching to getting in and out of cars in a ladylike manner. And I practiced with girlfriends who are also suffering from Gender Dysphoria.

“Although as you know, I had a rather girlish face to begin with, I have undergone considerable facial feminization surgery. A male and female skull have basic differences, as any anthropologist will tell you. I had orbital rim contouring to modify my forehead, cheek augmentation utilizing implants, lower jaw chin surgery and thyroid cartilage reduction for my Adam’s Apple.”

“What about your body?” I asked. “Your breasts are fantastic.”

“You know, just the usual textured saline filled implants. Also a tummy tuck, hip, thigh and leg suctioning, and of course electrolysis.”

“Well, it’s just extraordinary. I can’t imagine anyone doubting you are a woman, Samantha.”

“Yes, Deborah, but for one important matter yet to be dispensed with.” She winked at me.

“Hey,” I joked, “You could write a new tune for the Dixie Chicks, a sequel to ‘Goodbye Earl’ entitled ‘Goodbye Dick.’ Are you going to have a funeral or something for your dick? How do you say ‘Goodbye Dick’ I wonder? Maybe you should see a taxidermist and get the sucker stuffed.”

“Great idea! Get it stuffed and stick it in my purse, and when someone tells me to ‘go fuck yourself’ I pull it out of my skirt, lift my skirt, and do it. That or get it pickled and exhibit it at the Tate Modern for a million bucks.”

“Geez, I wonder if Hallmark makes a card for this occasion, like ‘Sorry you lost your dick but glad you’re now a chick’ seems appropriate.” We both began giggling hysterically.

“They bury animals don’t they?” Samantha questioned. “I think I should bury my dick.”

“No, no, let’s slice it up for cocktail snacks! By the way, the proper way to say farewell to your private anatomy is to make sure the doctors keep you awake during the procedure and after they have snipped it and are lifting it away with the crane start your most heartfelt rendition of ‘I’ll be seeing you.’ I don’t even know what dysphoria means. Is that the opposite of euphoria?

“And Samantha,” I continued, “aren’t you just a little concerned about penis envy? And don’t you watch Oprah? According to the he/shes on Oprah recently, or trannys as the twit Brits call them, right before the ‘operation’ they all went into a state of denial, which included hallucinations. They all experienced nightmares and woke up screaming, ‘Where’s my dick?’ Fortunately the drug Tehrahydrocannabinal Flunitrazepam can be prescribed to mitigate this psychological trauma known as MMM, Missing Member Mania.”

Samantha wiped laughing tears from her eyes and got serious for a moment. “There you go, pulling my leg again. I know what that TF drug is; a combination of hashish and 'roofies,' you know the date rape dope. What concerns me the most about all this is that I’ll have to pee sitting down.”

“Yes indeed, the female anatomy is not conducive to standing. But at least you won’t have to stand in front of strangers peeing.”

“Hey, I liked that part. Whenever a dude would look over at mine, I’d say, ‘Wanna shake my snake?’ I got punched a couple times for that one. Yeah, and I’ll miss the graffiti over the urinals like, ‘Don’t look up here, the joke’s in your hand’ and ‘Don’t throw toothpicks in … crabs can polevault.’ Hey, I may have to pee sitting down, but no PMS, unless it’s psychosomatic.”

“Let’s go back down to the reunion,” I suggested, my libido having been somewhat diminished for the moment. My curiosity still overwhelmed me, wondering if anyone else would suspect that this beautiful woman had a big fat cock.

On the way down to the banquet room where the reunion was being held, Samantha and I concocted a bullshit story. Sam had been killed six months earlier, and Samantha, his wife, came to the reunion to meet all his old friends.

We sat on bar stools sipping ice water because we passed off as straight vodka. Like we weren’t already trashed enough. Guy after guy hit on us. Samantha gave them all the brush-off. She knew what she wanted; Jimmy Joe Jefferson.

While we waited on Jimmy Joe’s appearance, I continued to ask Samantha questions about “her” past history.

“Samantha, obviously you didn’t always look like a beautiful woman. There must have been a transition period. Tell me about that.”

“Well, if you insist. When I still looked more like a guy than a girl, across the bridge from where I lived an old trailer had been converted into an adult bookstore. It had everything there from magazines to dildos to movies. Also it had my favorite; the booths.

“This place was run by some gay guys and they pretty much did not care what went on as long as nothing happened that required the cops to be called. I had been frequenting this place for a few months to buy magazines and movies, and always wanted to go into the booths, but was a little scared. Finally one night I made up my mind that I would do it.

“I got there about 1:00 AM and the place was packed. Guys stood along the wall and I thought all the booths to be full so I stood next to one door waiting. I reached to try the knob and the door opened. No one inside. I went in and sat down and loaded up the machine with $5 worth of quarters.

“On both walls in the booth were holes cut out just big enough for a cock to slide through. Not being a virgin to sucking, I decided to immediately show off what I was wearing. I stripped my clothes off and stood there in a white bra and panties, feeling myself up when the first cock came through the hole. Mind you I had imbibed in a considerable quantity of alcoholic beverages before going that night, so I felt pretty high.

“I sat back in the chair, crossed my legs and started playing with this guy’s cock; not all that big but pretty nice. After a few minutes, I bent down and started sucking and it sure didn’t take long for him to cum, and then he just pulled up his pants quickly and left. I started watching the movies again and soon someone entered the booth. The first guy must have given this one the high sign because he wasted no time in dropping his pants and sticking his cock through the hole. I started sucking him when I heard someone knocking on the other wall. I looked and had another cock on the other side sticking through. So there’s me in my bra and panties with two cocks to play with.

“I alternated sucking each one, but I needed some action too so I slipped a condom to the one guy and he put it on. I bent to suck one, dropped my panties to my knees and backed into the other guy. I took it nice and slow into my butt, and he started pumping, as I continued to suck the first guy. Let me tell you that was heaven! The guy I was sucking shot his load in my mouth and when he left, I started playing with myself while still taking it up the ass. Soon I came and I quickly got dressed and left.

“Then this time I …” Samantha paused. Jimmy Joe approached.

Jimmy Joe achieved considerable fame as the chief stud of our graduating class. Quite the star athlete and really dumb shit. Rumor has it he banged all twelve varsity cheerleaders and the forty year old wife of the principal and cheerleader coach. Oh yeah, and Jimmy Joe relentlessly harassed and humiliated the ultimate geek, my friend Sam.

Although Jimmy Joe’s eight-month pregnant wife accompanied him to the reunion, he still found it necessary to get him some strange stuff. He had his eye on Darla, the homecoming queen who now stripped and did porn, until he saw Samantha sitting on that barstool. Doing his studmuffin routine, Jimmy Joe strolled on over and struck up a conversation with Samantha.

“Hey, babe, you are hot! I already got the scoop on you. You are the late Sam’s wife. What did you do, fuck him to death? My condolences but I can’t believe a twerp like Sam got a foxy lady like you. What, he had money?

Samantha played along. “Yes indeed he had money. But it’s mine now.”

They got real cozy. I moved over one barstool. Jimmy Joe put his hand on Samantha’s knee, and ran it right up her dress and struck pay dirt. He put his hand on her cock and I thought the shit was going to hit the fan.

“What’s that?” he blurted, quite startled.

“A Kotex overnight maxi pad, silly boy. You know, the ones in the blue package. Bad time of month. Very bad.”

“Oh well, I guess I’m not getting any tonight.”

“What, don’t you like blowjobs?” Samantha whispered in Jimmy Joe’s ear. “Just because you can’t do me doesn’t mean I can’t do you.”

I stood up and said I had to go powder my nose and dragged Samantha along with me. When we got there, I stammered excitedly, “Hey, I want to watch this.”

Samantha gave me the key to the room. “Hide in the closet. I have an extra key.”

Half an hour later Samantha and Jimmy Joe entered the room. Soon she dropped to her knees and undid his pant. Oh my, he was wearing these camouflage boxer shorts. Samantha lowered them. Jimmie Joe had a huge boner before she even touched him. I felt like a peeping Tom but I couldn’t help getting excited. I slipped my hand down my panties and began to tease my clit.

I thought I could really suck some cock but I had to give kudos to Samantha. Such enthusiasm! She even taught me some new tricks. Particularly impressive was the fact that she could get Jimmy Joe’s entire cock down her throat.

Five minutes later Jimmy Joe was screaming, “Suck me you fucking whore!” as he pulled out of Samantha’s mouth and shot cum all over her face and hair. He grabbed his cock and rubbed the head around her lips and she swallowed and licked up as much as she could.

Samantha stood up, and said, “OK baby, now it’s your turn to suck mine.” She unclipped that tulip-wrap dress, the top had already been pulled down to reveal her breasts while she sucked off Jimmy Joe.

Next Samantha took both hands and slowly and seductively pulled down her ‘serpent purple’ thong.

Jimmy Joe’s eye’s bulged out of the sockets, he grasped his chest and collapsed to the floor. I immediately called hotel security and medical personnel arrived quickly. But it was too late. Jimmy had passed away.

I stayed in town an extra couple days for Jimmy Joe’s funeral. Samantha didn’t. Massive heart attack the coroner said, likely brought about by some sudden traumatic event.