My First Ladyboy


I was in my forties and was bored with life. My job sucked, my night life was the same over and over. Bar hopping hoping to get lucky and pick up some woman who would fuck me and not be crazy in the morning. Or maybe a hot guy just for the change of pace. Guys were just about the sex and usually didn't bring any baggage.

So I was surfing the internet and getting turned on to sexy places I had never dreamed of. It started with threesomes with bisexual guys and that really turned me on. Then I was looking at strictly gay stuff and these guys acted like they loved eating ass. I really did too and having eaten every woman who would let me and always tried to lick their ass if they were willing but only found one woman who would eat mine. Too bad she wasn't a keeper, just a one night stand for each of us.

All the guys I had been with were pretty much a blow and go. Both of us would blow if I was lucky. I had fucked and even been fucked a few times.

Then I saw my first she male and now I was really hot. They looked like beautiful women but had cocks. I thought if one of them would lick my ass I would do anything for her.

I was looking at girly boys and got on a chat site that catered to them. I had a few short chats with some but was kind of nervous about going farther. But one kind of made me hot. We talked a lot before we got to sex and then things heated up. She wasn't new to the life and but was keeping it from the outside world only dressing up at home. She had a couple of dates that were unsatisfactory for her. She went on to confess sucking cocks at adult shops in movie booths thru the glory holes and a couple of blow jobs at gay hang outs in a local park.

She confessed that she loved sucking cock and tasting all the different sperm she swallowed. Shyly she confessed she even liked being fucked but wanted to be treated with respect and most of her partners had taken their fears out on her. All only verbally but she was hurt by it and was afraid of meeting a new partner unless she felt respected.

I must of made her feel comfortable because she invited me to her place and we set a date. I asked her to dress up in her hottest outfit and be ready for anything just in case I could let lose my hang ups and explore my fantasies and hers.. I was wild beyond my hottest imagination.

I had read so many stories online and seen so much I shaved my cock and balls. I even did my ass hole. It was then that I slipped even farther into the fantasy and gave my ass a good douching. That made me even hotter. I liked sliding the tube into my ass. The few butt jobs I had been part of in the past were unplanned so they weren't as pleasant as they could have been.

I went to her address and was stalled outside her door. I couldn't ring the bell! Frozen in fear I finally pushed the button and quickly the door opened but on the chain. We had exchanged pictures, even sexy ones, but she wanted to make sure the person she was expecting was in fact at her door.

As she looked me over she smiled and said: "Just a sec hon."

As she pulled me inside we got our first real look at each other. She seemed happy with my appearance and I was wowed by hers. Tall and slender she had black heels and hose that went to her hips. Kind of panty hose but open in the front. She had sheer black panties that hugged her cock and balls tight to her body. Her balls were drawn up to her and I could not see their size, but her cock was hard to hide! Laid to the side it had to be seven inches and equal in thickness, and she appeared not to be hard. She had a sort of diaphanous top covering her small bra, also black but leaving a bare mid-drift. She had dark eyes with black eye shadow and ruby red lipstick being the only color other than black in her appearance. Long black hair and pleasant smile completed the affect.

She seemed equally happy with my looks as she stepped to me and caressed my quickly hardening cock.

"Is this bad boy for me? I think he likes me if his movement means anything." She says stroking me. "Do I please you?"

"Baby, you are more than I had imagined!" I exclaim as I reach for her cock too. It feels wonderful in my hand and she is swelling too. I wonder just how big she will get and if it will all fit into my mouth?

"Here let me make you more comfortable she says as she undresses me barley inside the door. When I am down to my underwear she pushes me gently back until I feel an arm chair behind me and fall into it. She is running her hands down and over my chest, stomach and legs. By passing my cock and balls, which are straining against the material.

Finally she covers my crotch with her outstretched fingers and as she strokes my cock with one hand she cups and squeezes my balls with the other.

"Would love like to get out of these and show me what you have for baby?" She asks seductively and reaches for the waist band. I lift my ass off the chair as she pulls off my underwear.

"My what a nice present you have for me. Here slide forward so your other toys can hang free for me." She says guiding me so that my cock is bobbing straight up and ball sack hangs down over the edge of the chair.

Knowingly stroking my shaft and rolling my balls in their sack she says to me: "Tell Billi what you want I need to hear it, say it out loud."

"Billi, I want you to keep caressing my balls and cock. I want you to lick my balls and suck my cock. And I want you to make love to my cock until I shoot my load down your throat. Is that what you want to hear?" I say.

"Like this?" She says as she sucks one of my balls into her mouth and runs her tongue around it. "And this?" She asks as she takes my cock head into her mouth and runs her tongue around it too.

"Oh yes, that's perfect." I moan.

"How about this?" She asks as she takes my shaft down her throat.

I can only moan and nod my head.

As she sucks my cock tightly she runs two finger tips behind my balls to my taint and presses inward bringing more deeper moans from me.

"But how about this, how do you like this?" She asks looking me right in the eyes as she runs those finger tips over my anus and pressing on the forbidden opening.

"Oh, yes, that too, especially that too." I can only beg.

"Now we know things you want, what will you do for baby? Will you do these things for her?" She asks coyly.

"Baby, I will do all those things for you and more!" I gladly say.

"Say it out loud, I need to hear it and you need to say it." She commands squeezing my balls and pulling down on them as she also squeezes my cock shaft while running her tongue over the tip.

"Billi, I want to suck your cock too, I want to feel it sliding in and out of my mouth and between my lips. I'll suck your balls. I want to lick and kiss your ass and if you want I would love to feed my hard cock into it and fuck you. I bet you can get me to do a lot of things I have done before and some I might have not. Is that what you want to hear love?" I confess.

"Yes, I love to hear all that nasty shit! I do it all but still love to hear it too." She confesses.

"Suck me baby, suck my cock and make me cum down your throat. And, oh God if you keep fingering my ass hole I'll cum so fast!" I moan.

She goes back to work on my cock and anus. She sucks me like a champ and the way she so willingly fingers my ass makes me think she has done this before. It excites me thinking she is a slut and is sucking me off now. I want to hear about all the cocks she has sucked and probably fucked too. I want to tell her about the cocks I have sucked too. The pussy I have eaten too if she wants, but right now all I want is her mouth on my cock and fingers in my ass.

As she sucks me I run a hand through her hair and find it is not a wig and that makes me even hotter. Our eyes meet and she is beautiful with her mouth full of my cock.

She has a finger deep in my ass now and as I throw my head back in ecstasy I see a bottle of lube on the side table. I reach for it and she offers up her hand and I lube up her first two fingers. Without taking my cock out of her mouth she groans letting me know that if I soon want two fingers I am a slut too and she may be in for a fun night!

After I drool some lube over her fingers she quickly returns to my ass hole. One finger easily slips in over half way and smiling as well as she can with a mouth full of cock she presses the second finger in beside the first.

Still working up and down my cock she has my nut sack in one hand and two fingers in my ass.

"Come on fucker, talk to me, be more than just the cock in my mouth, tell me everything you like, what you want. I bet you can't ask me to do anything I won't do!" she says challenging me.

"Right now I want your mouth on my hot cock, so shut up and suck." I say.

Softening my voice I tell her: "I want you to suck me until I cum down your throat. Keep fingering my ass, I love ass work. I love having mine worked over and love making hot wet love with my mouth on someone else's. I will love doing yours."

"I'm gonna cum in your mouth soon and then I want to suck that big fat cock of yours until you fill mine. I want cock then, all I want is cock but after you cum I'm gonna roll you over and eat your ass like no one else has you slut. Then when you beg for it I'm going to push my hot cock into your slutty ass hole. I'm going to fuck you until I dump my burning load into your guts."

"I think you are a cock slut and just knowing you have sucked a lot of cock and fucked some makes me hot! How's that my little cock sucker, is that what you want to hear?" I tell her while keeping eye contact with her.

Breaking loose from my cock she says, as she moves her ball squeezing hand to stroke my shaft: "I love it! Yeah I'm a cock slut, I sucked my first one at 13 and haven't stopped for almost 8 years. I love yours in my mouth and want to feel and taste your cum. I want you in my tight ass too. Sure I've been fucked but I bet you have never fucked anything as tight as my little boy hole."

"But, you know what? With all the cocks I have sucked and fucked you are the first guy who I think really loves it without any hang ups. A lot of guys can't get out of here quick enough after they cum and I hope you aren't one of them. Which kind of fucker are you?" She continues.

"Keep sucking and after I fill your mouth, kiss me and find out who I am my bitch, now get back to work. You might be the best cocksucker I have ever been with if you would get back to it." I tease.

By now the sun is setting and the room is filled with a warm red glow really setting the mood as she gets back to her wonderful sucking. All kinds of men and women have sucked my cock for all kinds of reasons. Some little better than a hand job and some excellent. Some guys and women really like sucking cock or at least act like it. But this bitch really loves it. I can tell she would suck a cock just for the joy of it without any reciprocation expected and I am just the same. I love sex. Period. No deciding whether it is straight, gay or bi. Just sex. The best would be a threesome with a bi guy so I can eat a cunt filled with someone else's cum and suck her juice off his cock. I can't wait for that to happen.

But right now the slut sucking me off is as close to perfect as it gets and with her working my ass over so well I quickly shoot my hot creamy load into her mouth.

"Oh fuck baby that is so good! Keep fingering my ass and don't stop that wonderful sucking. Oh fuck you're beautiful. Try to save me some of that juice." I say shooting my load into her wonderful sucking mouth.

Finger fucking my ass and sucking faster and faster as I shoot. As my orgasm slows she slows her work so perfectly that when my cock is softening and sensitive she is sliding it out of her mouth as she does the same with her fingers.

All I can do is stretch out my legs lay my head back and sigh.

When I open my eyes she is still sitting between my legs and I wrap them around her and pull her up to meet my lips. She rubs her face across my still semi hard cock and slides her body across it until our faces meet and I take her face into my hands and kiss her. She opens her lips and I slide my tongue into her mouth to find my cum. As I hungrily eat her mouth she feeds me my cum, a lot of it, and it excites me so that combined with her rubbing her hard cock inside her panties over mine, I start to harden too.

"Maybe you are one of the good ones." she says as she licks some of my cum from her lips. "Do you want my ass now, love?" She says.

"No I want that fat cock in my mouth! I want to taste your cum first. I can't fuck your cute little ass when you have that big hard on going unloved." I tell her as I roll from the chair and guide her up to be seated like I was.

As I got comfortable between her legs I gently spread them as wide as I could. There was the object of my lust, her fat cock and balls. She was shaved clean and uncut, just like I love my cocks. Having her black nylon covered legs around me made it so much hotter. I ran my fingers down the length of her hard cock. It was held tight to her body at her thigh. It was the biggest I have ever touched. She was easily eight inches long now and equally fat. As I leaned forward to cover her cock head with my lips I cupped her balls.

Moaning with desire I say to her: "Baby, your cock is so fucking nice. I just love it."

As I run my lips up and down her length I am getting it wet with my spit. I love it covered by her panties but have to have it in my mouth so I pull the top down just enough to let her cock pop free and I pull her balls out just enough for me to feel them. Her cock is beautiful and as I cover the head with my mouth I pull her balls free and down from her body. I am caressing her sack but her cock is the object of my desire. I am running my tongue around the head and under the foreskin. I pull back and suck her soft skin so that it is stretched as far as it will go. I suck it like it is a separate being but her cock quickly reaches its full dimension and pulls the skin back to tightly cover the crown.

Still playing with her balls I stroke the impressive shaft as I suck the end, running my tongue over her. She is squirming and making all kinds of sex noises so I know that she is loving this and it excites me even more.

I wanted this cock more than any before it. I was a little unsure with my first but once I felt it slide through my lips and onto my tongue I was hooked. I wasn't about to give up women this was just more.

Trying to bring her to new heights and fuck her with my mouth I yearn to try something I have never done. I have sucked some cocks but never let one fuck my mouth as I lay back passively. One of my favorite stroke photos is of some naked stud on his back with an equally hot stud kneeling over his face fucking it.

I tell her to stand up and turn around as I lean back with my head lying on the seat of the chair. I ask plead actually: "Fuck my mouth, put that fat cock in my mouth and give me your seed!"

As I settle in she has to squat over my face as she feeds me her throbbing cock. With her legs spread her balls hang down as she feeds me her hot manhood. As her cock head passes my lips to find my wet tongue I reach up to caress her hanging ball sack and hear her moan.

Can a woman have a manhood? Whatever, it is way too big to be a clit, maybe just cock.

As she pulls back to enjoy the feel of entering my hot wet mouth I say: "Come on, fuck my mouth. Push that beautiful cock in me."

As she does just that my eyes roll back in my head as I wantonly suck her into me. My lips and tongue are the center of my being as I eagerly suck her cock into my mouth. "Fuck me" this feels wonderful! This beautiful cock fucking my mouth as I caress her balls with one hand and her ass cheeks with the other. I could almost cum with no stimulation of my cock.

Taking my head into her hands she works this hot man-ness in and out of my yearning mouth. I suck on her using my entire mouth, working my lips and tongue over her until we have a rhythm experienced by few lovers. This has no name, no label, it is pure pleasure for both partners and we are swept up into a world of pure erotic pleasure.

All too soon I feel her nuts tighten up into her body and I hold her by the ass as she fucks my mouth rhythmically and finally climaxing into it. As she shoots her hot cum into my mouth she says: "Look at me cock sucker, look me in the eyes while you suck my load from deep within my balls."

Our eyes meet and we are joined by more than cock and mouth, we are joined on a much higher level and it makes my balls tighten up into my groin and as my cock painfully grows, throbbing like I was the one cumming. My anus aches with yearning to be filled as part of this experience.

I try to hold as much as possible before she cums so much it fills my mouth and is forced out between my lips and her shaft to cover my face. I am forced to swallow some but am able to hold enough to savor her essence. This is one of the most sensual, sexual, erotic things I have ever done and my cock and balls scream for relief as her thrusting slows and she gently pulls her now tender cock from the heaven that was my mouth. To give this much pleasure to another is joy itself.

Standing with her legs bent and spread around my face our eyes are still connected when she says: "God, I need you to fuck me right now!"

"Turn around and give me your ass so I can make love to it like I loved your wonderful cock. Spread your cheeks and show me where you want me to make love to you." I pant.

She does just that and as she rests her hands on the chair arm she lowers her ass to my outstretched tongue. As it enters her open anus she moans and with shaking legs almost loses her balance but I have an ass cheek in each hand and support her. I cover her ass hole with my mouth and kissing it wetly I work my tongue into her. She is no virgin to anal play and easily welcomes my tongue. I feel her ball sack come to rest on my chin and what can only be her soft but long cock. I wonder can I make her hard just by eating her ass?

Soon she says that she cannot stand it any longer and must get in a better position. Standing she helps me up and kisses me forcing her tongue into my mouth. She must be able to taste all of the flavors I have just experienced and I try to feed her the last of her cum as I turn her to be seated.

I see the bottle of lube on the end table and ask her to pass it to me. Opening it I cover two fingers with it and quickly run them over her opening.

I had barely touched her when she grabbed my hand and forced my two fingers deep into her ass. I started to work them in and out while twisting on the out stroke when she said: "Oh fuck me baby, fuck my ass like you own it. Use your fine cock now, fuck me now."

Wanting to please I slid my fingers from her hot ass and covered my cock with more of the tube and pressed myself to her ass hole which easily opened up for me. Always aware of how easy you must be when fucking someone's ass I was being careful.

Leaning back in the chair she rolls her ass up making it to enter her. She wrapped her legs behind me and pulled me deep into her bowels. Once I was balls deep inside her she pulled me down to wrap her arms around me and thrust her hips up forcing me even deeper than I thought I could go. Our faces were so close it was only natural to kiss and we did with open mouths and with lots of tongue.

As I was working my manhood in and out of her ass as we kissed like familiar lovers. It was hard to believe we had really just met tonight. I have had sex with quite a few guys but I always thought of them as guys and I was just after cock. To suck or be fucked by was my object but with Billi I thought of her as a girl or woman because that is who she thought of herself. I don't think the cock was better but in the experience this has been special. I was looking for cock and all that went with it but wanted some of the softness, romance if I am honest, that only a woman can bring. Or someone like one.

Report Story

by69plus1© 5 comments/ 83832 views/ 31 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: