Mikes First Transgendered Pt. 20

20

Please read parts 1 -- 19, before reading this.

Our night with Walter.

David and I are about 14 months in and moving along greatly. I have enjoyed him in my life and have fully transitioned over to Samantha since our 1-year anniversary. During our time together I have met several of David's friends as he has met several of mine. One guy in particular, Walter, is quite he unique character.

Walter is a middle-aged man David used to work with. Walter is coming up on 45, he has a receding hair line, a big ole beer belly, quiet, shy and kind of an outcast. Walter comes by David's a lot to get out of his house and away from his wife. From what I've been told and heard through conversations, Walter is married to this rather large, big-mouthed, aggressive, obnoxious pig. He's stuck in the marriage because she doesn't work and they have 3 kids together. Walter probably hasn't had a blow job from his wife since their wedding night and I would venture to say their sex life is all but non-existent. Walter was one of the first people to know David was gay and accepted him without reservation. Walter knows about David and I and has even seen prior to my transition; and now as Samantha

One evening at David's the three of us were sitting around having drinks, playing cards and just passing the time, when Walter let it slip that he was intrigued by our relationship. Over the course of some mild questioning Walter admitted he thought about homosexual sex and has even watched "tranny porn," masturbating to it when his wife goes to bed early or he has time alone. David and I are grateful for his openness and can appreciate watching something different or new, or in his case, out of his normal realm.

After Walter leaves David and I continue talking about his situation. We both know that Walters not gay, it's just that he hasn't been turned on, made love to, or at least given a good sexual experience in a long time. After days of thought, I suggest to David - if he agrees - that we should invite Walter over and let me give him a blow job, just so he gets some relief from his lack luster sex life. David and I know whatit's like to be alone, in a sexless relationship and how hardit is to find that spark that keeps romance and fantasies alive. Doesn't matter if you're, Straight, Gay, Lesbian, or just Bi-Sexual. We all have had our moments alone, without someone to love without experiencing something fun, erotic or even daring.

David ponders on it for a few days knowing it's hard to watch your significant other with someone else, but he also realizes how unloved and unfulfilled Walter must feel. David agrees with my thoughts and decides to propose the idea to Walter. At first, I believe Walter was a little taken-a-back by the offer, but after some consideration he is receptive to the idea, as long as it stays between us and I am dressed as Samantha. I agree and we make plans for an upcoming night.

David orders me a new dress for our special occasion and I piece together the sexiest outfit I can find that night. David tells Walter to be over at 6:30 for a romantic dinner for the three of us. The dress David bought for me is a long maroon flowing evening gown, with an open top and mini-straps. I compliment the dress by wearing a pair of black panty hose, matching black panties, a strapless bar, my breast forms, a long blonde wig, with my pearl necklace, two-inch black high heels, my make-up done, nails painted and a light spritz of my favorite perfume. Walter arrives and I greet him at the door. He gives me a big hug and gives David a man hug. We sit down and have dinner having several glasses of wine. All three of us are nervous and uneasy for a while. But, throughout dinner, sipping wine and just communicating, the tension starts to ease. After dinner David and Walter head to the front room as I clean up.

I join them later and continue serving wine as the night progresses. I am horny -- because I am dressed up more than a usual Friday night -- but hornier because I'm hoping to suck a new dick tonight. In all reality I wasn't sure if Walter was going to go through with this. He's never experienced homosexual sex and as close as he and David are; and as much as I may look and dress like a woman, I still have boy parts. Truth be told, I really have no interest in Walter. He wouldn't be someone I would date if I was single, but the thought of experimenting and giving someone new a blow job, is a turn on for me.

As the night progressed, conversation flowed, tensions lifted and the more buzzed we got from the wine, Walter seemed more relaxed and excited about our adventures. When the time came, I asked him; "Would you prefer to watch David and I first to make sure you're okay with this, or should I just focus on you?"

Walter replies, "You and David first."

David is sitting to the left of Walter on the couch. I lean down and kiss David softly on the lips. Our mouth's part and we deepen into a heated French kiss. I feel his hands caressing my fake breast as my hands rest on his chest. I get down onto my knees and unbutton his dress shirt. I softly kiss from his neck, down his chest, stopping to suck on his nipples, making my way down between his legs. I unbuckle his belt opening it up. I unbutton his pants button and unzip his pants. At that moment I actually realized I am a bit nervous myself. I have someone watching me as I am about to give my boyfriend a blow job and knowing "the watcher" is next.

But I can see Walter's eyes are affixed on me as my hand reach down into David's boxers. David moans as I grab a hold of his cock. He gets hard in my hand as I begin pulling it out of his boxers. Walter's eyes light up seeing David's dick coming out of his pants with my hand wrapped around it.

I slide my hand and away and grab at the side of David's pants. He lifts his hips and I slide them off tossing them to the floor. I reach up again along David's hips and slide his underwear off. David is now naked from the waist down, with his hard cock standing erect. I grab a hold of his shaft and slowly start stroking it as I look into Walter's eyes. I lean forward and down and place David's dick in my mouth. I slowly bob up and down on it as David eases back in his seat. My motion is soft and erotic. A slow up and down as I'm sucking his cock. David's hands are on the back of my head as I swallow every inch of his cock down my throat.

After a while of sucking David's cock, I take my left hand a place it on Walter's left thigh. I hold it there for a few minutes letting him get used to my touch. I slowly slide my hand back and forth and up and down his thigh getting ever closer to his crotch. Walter doesn't seem to mind and is clearly watching me sucking on David's cock. I finally reach Walter's crotch area as my hand softly and slowly cups the bulge in his pants. I feel him jerk back in fear and surprise, but he rests back down and just lets me keep feeling him up.

I slowly and gently rub up and down his bulge getting him more and more turned on. I feel Walter's hand cover mine as I continue rubbing his dick and balls over his pants. I pull David's cock from my mouth and look over at Walter. He is turned on and assumably partially hard in his dress slacks. I shift my whole body over and I get in-between Walter's legs. The look in his eye was of fear and shock, but he knows this is all for fun and experimentation, so he's going with the flow.

I spread Walter's legs apart further and start using both of my hands to rub up and down the top of his legs and inner thighs over his pants.

I ask Walter, "Are you okay with this so far?"

Walter replies, "Yes".

I slowly push my hands all the way up passing his budge to his belt. I unbuckle it and start rubbing his bulge more. I softly and slowly caress him more wanting to make him feel comfortable and secure. I reach for Walter's button and unbutton his pants and unzip them. I see Walter is wearing a tight pair of white underwear. I reach and pull the flaps of his pants further open and downward so I can slide my hand into his pants over his underwear.

Walter arched back and gasped as I reached my hand into his pants over his underwear, getting my first feel of his dick, which was only partially erect. I rub over and across his cock, still hidden in his underwear, until I feel him respond more. I remove my hands and grasp at the side of his pants along his hips. Walter is definitely nervous, barley lifting his hips, making it hard for me to get his pants down. I pull his pants off and throw them onto the floor and slowly start sliding my hands up and down his legs again working my way back towards his cock.

I can see Walter is starting to get harder, because the white undies are starting to pitch a tent. I place my hands at Walter's hips and start to slide his underwear off. He is really leery at this point and probably rather embarrassed, but lets me pull his whitey tighties off. His dick is smaller than David's and mine. It is short, stubby, unshaven and only partially hard.

I tell Walter, "It's okay, you're going to love this."

Walter smiles at me and looks over at David. David is now affixed on us and seeing his buddies dick and it's exciting him. I place my hand on Walters cock and slowly start rubbing, pulling and stroking on it trying to get him harder. I can tell he's beyond petrified and scared at what's taking place, but I will make sure by the end it will be the best blow-job he ever had. I lean forward putting Walter's partially hard cock in my mouth. I slowly suck up and down on it, trying to get him fully erect. After a bit of sliding up and down and the flicking of my tongue around his tip he starts getting harder.

I take his cock from my mouth and hold his shaft in my fingers as I lick up and down it, making heated sexual eye contact with him. A look of extasy is brewing on Walter's face and he is getting more excited about this. Finally, Walter is fully erect. I place his hard cock back into my mouth and slowly start bobbing up and down on him. I can take his cock all the way in my mouth without gagging, so I proceed to jam it deeper and deeper with every thrust. I start hearing Walter moan aloud and out of the corner of my eye I see David shift to his right hip, facing Walter. I watch as David begins stroking, rubbing and caressing his own cock as I am blowing Walter.

In my younger days, like most men, I had fantasies of a FFM threesome. And throughout some of my dating and experimentation of years past, I managed to have a couple of them. I was the boy with the two girls. And I openly admit this now, because I wouldn't have back then, there were days -- even before all of this -- that I fantasized about having sex with a man.

But since Sara and Enna and now David, the fantasies have shifted to having two men at once. Two cocks at once! Being "the girl" of that MMM threesome. And now it looks like my fantasy will come true, as I sit here on my knees giving Walter a blow job, while my boyfriend is involved.

As I rest on my knees face buried in-between Walters legs, my panties are budging and my ass is begging to be fucked. My fake boobs rock back and forth as my head continues bobbing up and down on Walters hard cock. I take it out of my mouth every so often and stroke him with my hand as I look deeply into his eyes. I can still see David in my peripheral vision, stroking his cock. I am past horny; I am rock hard and really want my dick played with too. I slide Walter's dick back into my mouth as my hand slides under my dress and I begin rubbing up and down the inner part of my thighs, over my silky panty hosed legs.

***For those who never had the opportunity or pleasure of being cross-dressed. To feel a pair of sexy panties holding in your dick, coupled with a long flowing dress over panty hose and high heels, while giving head is beyond imagination. ***

I love being dressed, being a woman; on my knees sucking cock. And now I'm giving a blow job to a friend, while my lover is watching and stroking himself. As I continue sucking Walter off my hand is cupping, grasping and dry stroking my cock inside my panties making myself harder and hornier than before. The feeling is beyond amazing!

For the next few minutes, I continue sucking Walter's cock bringing him closer and closer to orgasm. I hear his breath start to get heavier and he is moaning out small mumbling words as; "umm yes, oh yes, oh yah."

His body is light shifting back and forth and I have no doubt he's enjoying every second of this blow job. When I look up again, I see David and Walter are engaged in a deep kiss and I about shoot a load in my panties. I never expected David to even consider making a move on Walter, but I guess hormones, got the best of them both. My cock is bulging and throbbing as I watch them make out. My left hand and arm are resting on Walter's right leg and I stop fondling myself and slide my right hand over to; and up David's legs finding his hand wrapped around his hard shaft. I start stroking David off as I continue sucking Walter cock.

I hear Walter moaning through his nose as he and David kiss. He is about to cum and I am awaiting my prize. I suck harder and deeper and faster hearing his breathing increasing, as loud slurpy sucking "blow job sounds" emanate throughout the room. As my speeds and depth increases, I feel his fully hard boner sliding in and out of my mouth making me want it more and more. Walter starts to whimper more and his legs start shaking as I feel his cum start shooting into my mouth. His dick pulsates and shakes back and forth with every blast of cum he's releasing. He is moaning loudly into David's mouth as he ejaculates deep down my throat. My hands grasping and squeezing David's cock as my head bobs up and down swallowing every drop of Walter's cum.

As I slow down, Walter's breathing slows and him and David break from their kiss. I keep Walter's cock in my mouth for a minute or so longer than usual, just feeling his boner and making sure I get every last bit of his cum. When I pull his cock from my mouth, I lick my lips and moan, "Umm."

I shift back over to David get back in-between his legs, look up at him and say, "Your turn baby."

David shifts back on to his butt. His cock rock hard and waiting for attention. I lean right down and put his throbbing cock back into my mouth and start bobbing up and down on him. Tonight, I am the blow job queen and I fucking love it. I continue sucking David off as I see Walter siting there staring in awe. I suck and lick David the way I know he likes his blow jobs. It doesn't take long until I feel both of his hands on the back of my head. lightly ramming my face further and deeper into his lap. He's pushing his cock as deep into my throat as I can take it almost gagging on it. I slurp and suck his cock until I feel him start breathing heavy. He's whimpering, "Yeah baby just like that."

I know he's about to cum, so I pick up my pace and suck him as hard and deep as I can.

David moan outs, "I'm going to cum, I'm going to cum."

My cock is literally pulsing in my panties, my asshole wide open wanting to be banged.

I feel David start shooting his load deep in my mouth, his cum swirls around my tongue and teeth. I continue slurping up and down making sure I get every bit of his heavy thick hot white load. I look out of the corner of my eye to see Walter is rock hard again and absolutely affixed on David cumming in my mouth.

When David finishes, I can't take it anymore and I need to cum.

I stand up, reach under my dress and slide the pantyhose down to mid-thigh. I pull my dress up holding it up with my left arm, as my right hand pulls and lowers the tip of my panties down, setting my hard cock free. My cock is bulging and throbbing and needing to be played with. David leans forward and wraps his mouth around my shaft, I moan I pleasure. I feel his mouth sliding back and forth along my shaft as I stare at Walter. I am in absolute pleasure looking down on him as he's watching me getting my blow job, after I swallowed down two loads of cum.

I am so turned on, knowing how turned on he was getting a blow, and now he's watching David sucking me off. We stare deeply into each other's eyes as David is blowing me and it drives me to an even higher hormone level. I switch hands to hold up my dress and reach out my left hand towards Walter. Walter reaches up with his left hand and grasps my hand. I stand there holding hands with Walter, keeping deep eye contact with him, as David sucks my dick. Just looking at him sitting there with a partially hard cock, knowing I just gave him head, gave David head swallowing down to loads of cum, and now getting head makes me harder than I have been in a long time.

I moan out, "OMG David! I'm going to cum."

And before I am even finished my sentence, I start shooting my load deep into David's mouth. My explosion is tremendous and long lasting. I can't stop cumming as David continue sliding back and forth sucking my cock. My legs shake and my body tingles as I release every drop.

After David finishes up and withdraws my cock from his mouth I stand there, rock hard, sweaty and catching my breath. I look down and see my boyfriend bottom less with a flaccid cock and sitting next to him is his buddy also bottomless with his partially hard cock as I stand here holding my dress up, dick sticking out of my panties slowly coming down from this orgasm.

Walter left a while later and whispered to me as we were hugging goodbye, "That was the best blow job I ever had."

I smiled and whispered back, "I'm glad to hear."

David and I cleaned up a bit more, talking about our night and getting ready for bed. We both admitted how fun and erotic it was to experiment with Walter and to try something new. I changed into my long white night shirt with just my panties on and climbed into bed. As we laid in bed, I was so aroused, so excited and so ecstatic that I had just given two different men a blow job tonight. I was actually proud of myself, that even though I wasn't interested in Walter, the opportunity for a threesome had arouse and I took full advantage of it.

In the dark quiet of our room, I laid there in deep erotic thought. Thoughts of what had just transpired. Fulfilling a MMM threesome fantasy while transitioning. What lies ahead for us. Sucking two guys off. But...wait... What about 3 men, or 4? My mind raced; my creative thoughts took over. What if David invited Walter and/or a few gay guys from the bar over for a football game and I sucked every one of them off throughout the night. I could be the waitress / maid, serving food and drink, dressed up all sexy. And when one of them wanted a blow job, I'd take care of their needs. All kinds of dick! All colors and sizes. OMG... I want this.

The vivid fantasies in my mind, got me overly aroused. I was budging in my panties again and my ass was throbbing and pulsing. I wanted to suck more dick. I wanted a lot of cock. I needed to be fucked! David was just about asleep when I started rubbing and touching him, trying to arouse him and seduce him. I wanted to give him another blow job, I needed more cock. I need to have a dick in my mouth again. I needed to be touched, but more importantly I needed to be fucked.

After a bit of seduction, David got aroused again and I went down on him. After sucking him for some time, I climbed on top of him and rode his cock. I came within minutes of him penetrating me, while thinking about a room full of men I could suck off. But then, my focus returned to him fucking me hard and deep -- like he should -- until he came deep in my ass.

The next morning, I started it all up again after breakfast, when without a word, I got down on my knees in front of him while he was sitting on the couch and sucked his dick until he was hard and ready. Eventually he slid off the couch and up behind me and fucked me from behind until he came again. I didn't cum that morning. I didn't need to. I really didn't want to. I just wanted to suck dick and get fucked in the ass. Funny how sexual desires change for someone, based on their situation.