3 comments/ 163064 views/ 3 favorites My First Ladyboy By: hornyrider At 27 I reckoned I had the best job in the world. Twelve months ago I'd been appointed by the London-based international group I'd joined some five years before, to monitor the performance of our agents throughout the Far East from South Korea down to Indonesia and across to Thailand. No doubt one of the deciding factors in my appointment was that I was unattached. A great deal of travelling was involved which I loved. I also enjoyed the first class hotels I stayed at, the wonderful variety of food and of course the company of the readily available women in many parts of the region. One of my favourite countries was Thailand which was just as well as our agent there was causing us lots of problems which required frequent and on occasions, prolonged visits. Early on I'd linked up with a resident pal, Ian, about my own age, who introduced me to numerous bars, massage parlours and other night spots in and around Bangkok. One night Ian said he'd take me to a special bar where there were usually some interesting girls to be found. On arrival Ian introduced me to a dark-headed beauty with lightly tanned skin and a very ample bosom which she did nothing to conceal. I was immediately aroused, the more so when she spoke in a rather deep sexy voice. After just one drink I suggested we move somewhere more private. She agreed and suggested we take a taxi to her nearby apartment. Tam's apartment turned out to be one large room with a large bed, a couple of chairs and a small bathroom with a shower, a basin and a toilet. Tam wasted little time in pulling me to her and kissing me open mouthed and passionately. I ground my full erection into her belly which caused Tam to say 'That feels just about my size darling. I'd love to feel it deep inside me but I've got my period. Don't worry though. I'm going to give you a blow job unlike anything you've ever had before.' Now although I prefer to fuck I'm quite partial to a good blow job so raised no objection when she unbuckled my pants, unzipped me and pulled both my trousers and underpants off before getting down on her knees and taking my aching tool into her mouth. 'Play with my tits' Tam breathed sexily while licking the tender underside of my cock before once again gobbling it down deep into her mouth. I pushed down Tam's blouse and took hold of two hard mounds of flesh which I squeezed and stroked while continuing to enjoy the ministrations of Tam's mouth and tongue on my eager cock. Despite my preoccupation though I took note of her unusually small nipples. Tam pulled off to draw breath and as she returned to her work she said "Fuck my face darling.' There was only one way I could react to that and that was to push deep into Tam's mouth. I'm a bit better than average length, a bit fatter than most but Tam accepted everything I had to offer. Tam was very obviously an experienced cock-sucker and I was delighted when she angled her head to take my knob into her throat. This was turning out to be one hell of a blow-job and I knew it wouldn't be long before I blew a load down her throat. Reaching up under my shirt with one hand Tam began pinching my nipple while with the other she inserted a finger in my arse hole. All this proved more than I could take and with one final thrust I exploded in her mouth jet after jet of cum spewing into her oral cavity. Tam waited until the flow stopped and then gently pulled off licking the fuck-cream from my shaft. Then she got to her feet and pressing her lips to mine dribbled my cum into my mouth. This was some woman. 'Let's lie on the bed for a while' suggested Tam and we both moved across the room and made ourselves comfortable, Tam spooning her back into me. 'Let me do something for you darling.' I asked. Tam remained silent. 'Let me stroke you clit and bring you off.' Again no response. I thought Tam had gone to sleep but then she said quietly 'If I tell you something will you promise not to get mad?' 'You can tell me anything you like and I promise I won't get mad.' 'Give me you hand.' I reached across and Tam guided my hand under her skirt and then placed it at the top of her panties. This I took as an invitation to slide my hand down inside. I did just that seeking her clit which I then intended to stroke hoping to bring Tam off. My hand groped and came to rest on what I first thought was an unusually large clit but I quickly realised was in fact a smallish semi-stiff cock. My first thought was to pull my hand away but something about the appendage I was now holding felt so good that I left it there. 'You're not mad? Asked Tam. 'No not mad. Just very surprised. I've read about ladyboys but you're the first I've come in contact with.' 'Do you like?' 'I haven't held another guy's cock since I was a boy but with you it's different. To me you're a very desirable woman and the fact that you've got a bigger clit than I expected doesn't change that. Yes I like but the absence of a hole is a disappointment I have to admit.' 'I do have another hole darling and you're welcome to use that. In fact I'd love to feel you deep in my boy-pussy.' 'I've never fucked anyone, boy or girl, in the arse though I have to admit I've thought about it.' 'Then why don't you try? Just pretend you're fucking a woman with a very tight fuck-hole. I'm sure you'd enjoy it.' 'OK. But first let me look at your cock. I want to understand everything about you.' 'Let's get undressed' said Tam. I agreed and stripped the rest of my clothes off while Tam shed her panties, skirt and blouse. She lay beside me spread out and naked. I moved down and took in something I'd never expected to see. Tam had a bush of fine black hair in the midst of which lay a small brown penis, about two inches long with a darker foreskin covering her cock-head. I peeled it back to reveal a pink knob. I felt for her balls but found nothing or close to nothing. Without thought I leaned forward and sucked the full length of Tam's cock into my mouth teasing back the hood and licking the soft sensitive spot under the head. 'That's so good darling. It gives me big warm feelings.' 'Can I make you cum.' 'No my balls are almost gone now because of the female hormones I take to make me more feminine. My tits of course are implants but the hormones help to keep them firm. My nipples are all mine. I only wish they were bigger. Now I cum more like a woman – inside. It's especially good when I'm being fucked in my boy-pussy. Are you ready for me? Let me feel your cock. Yes, it's hard again. Get on top of me.' I did as Tam instructed though I was surprised she didn't get on her hands and knees which I thought of as the usual way to arse-fuck. Tam reached behind her and took a pillow which she placed under the small of her back and then pulled back her legs exposing her dark brown wrinkled hole surrounded by matted fine black hair. 'Lick it darling. Make it wet. Don't worry, it's clean. Get it ready for your cock.' I have to admit I was somewhat reluctant to put my lips to Tam's arse hole or boy-pussy as she preferred to call it. Much to my surprise however the taste was by no means objectionable and I quickly fell into a rhythm of licking and sucking. By her murmurings it was clear Tam was greatly enjoying my tongue and my lips and as I pulled away I saw that her hole was slightly open, invitingly so. I moved up between her legs and Tam grabbed my stiff shaft rubbing the head around her wet hole. I was now leaking pre-cum freely and was getting increasingly aroused. Tam stopped her movements and placed my knob at her entrance. 'Push darling. Slide into me.' Despite my cock being absolutely rigid, I felt resistance, so unlike what I was used to in entering a well lubricated cunt. Then I felt Tam's arse hole push out and the head of my cock slipped into a very tight space. 'You're in darling. Just hold it a second and then push in slowly.' I did as instructed and very soon found my cock firmly embedded in the tightest fuck tunnel I'd ever known. The feeling was indescribably good.' 'Now fuck me darling. Fuck me as a woman. Make me cum inside as you shoot your love juice deep inside me.' I needed no further encouragement to begin a steady pounding of Tam's arse her legs locked behind me urging me on. Happily, the wonderful blow job I'd enjoyed just a half an hour before had taken the edge of my appetite and I luxuriated in the thrill of a long steady fuck embedded in a tight, hot hole. With Tam kissing me passionately I forgot completely that I was fucking a guy's arsehole. As far as my cock was concerned, and my head for that matter, I was fucking a highly desirable woman. As the saying goes, all good things must come to an end and I was not about to prove this old adage wrong. Before long I began to feel the ache in my balls start to overtake the pleasure my cock was experiencing and I knew that I would not be able to hold back the flow of fuck-cream for long. I began to pound Tam's hole faster as she encouraged me with her words and her body. Reaching down I found her little cock was stiff and on pealing back the hood found it quiet wet. At least her prostate was still working. With one final drive I pushed into Tam's bowels as far as I could reach and dumped jet after jet of cum deep inside her. I held my hard cock inside her relishing the gentle squeezing of her anal muscles. 'Jesus Tam, that was the most fantastic fuck I've ever had.' 'I'm so glad darling. Very good for me too' said Tam. 'You know I had this strong feeling for you when you walked into the bar. I wanted very much to be with you but was scared to tell you I wasn't totally female in case I frightened you away. Sorry darling. But after you kissed me and I sucked you off I felt very close to you and decided to take a chance.' 'Darling Tam you're the first ladyboy I've had anything to do with. I'd heard about them but never had any thoughts of being with one. Now I know better and I promise you'll see me every time I visit Bangkok in future and I'll do my best to make that as often as I can.' That was the beginning of quite a long association with Tam who proved to be a wonderful lover and very good friend during my frequent visits to Bangkok. After our first coupling she refused to take any money from me but of course I bought her many gifts. Although Tam was a working 'girl' I always fucked her bareback. Mind you this was before HIV and AIDS came on the scene. It would be a very different story today. 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. My First Ladyboy A fuck is a fuck is a fuck, but an ass fuck is just something special, exotic even. The sheer forbiddingness of it makes it so hot. It is nasty, exotic even because most women won't allow it and even fewer will ask for it. Guys, well it is usually part of it but never a guarantee and for me not always wanted. Now days most women suck cock, all fuck but few give up their ass. Any guy into it will suck cock and most of them will fuck you at least and near as many will fuck too. Still for me it is very special, that excitement of preparing your partner to be penetrated, the fingers, and the tongue, the spreading of the lube and finally that so special feel of your cock head spreading open that forbidden place. With a woman it is thinking that not every lover of hers has been where you are about to go. I am probably wrong about that but I like the thought. With guys everything is so primal. There is no thinking there is any love here, it is just pure sex. Animal lust, just fucking. All of this and more that I cannot verbalize runs through my mind. I know Billi has had cock in her ass before, probably many but she feels like I am the first to pass into this tight hot opening. How does the inside of someone's body always seem hotter than their body temperature? Oh Fuck! She is so tight as I pass all the way down into her. I can feel her welcoming me into her but she is so tight. As I hold deep inside her we kiss tenderly making love to each other's mouth with our tongues. Without breaking out kiss I roll my hips to slowly pull my cock back from her bowels. She grips me tightly like she doesn't want to lose me. I pull almost out of her and wait with just the head of my cock inside of her heat. As I push back into her she raises her legs so that her knees tuck under my arms. She closes her lips and I am driven to push my tongue into her mouth as I do the same with my cock. Releasing her grip on me I slide my pulsing cock into her as she sucks on my tongue as it enters her mouth. "Oh baby, you are touching part of me that no one else ever has. Fill me with your wonderful cock. Take part of me that no man ever has been able to touch. Oh fuck me, fill me with your cock." She tells me. As I find myself deep inside of her I cover her lips with my mouth and gently bite them as I slide my tongue back into her mouth. I feel her fat cock throbbing between us and her balls pressed to my groin. She tries to work her hand between us and I push it away to stroke her cock myself. I cover the head with my thumb and roll her skin around and then stroke her length. I match my cock inside her with my hand on hers and my tongue to fill and stroke her in time with each other. Things move fast for me now and before long I feel my balls tighten up and I start shooting streams of hot cum into her as she does the same between our bellies. I love the feel of a cock pulsating in my hand. To feel each load run the length of the member and know how much pleasure it brings and that you have done it! After we have both cum we are quite, she has slowly let her legs slide down my body to come to rest by mine and this causes my softening cock to slide from her ass making her shudder and wiggle her hips as it happens. Moving me to the floor she kneels beside me and says: "Are you staying? Because I need a shower if you want to... My First Ladyboy Ch. 02 We had just fucked ourselves senseless and Billi was leading me to her shower. After she adjusted the temp we got under the spray. First off was to clean my cock of the lube and cum. I leaned back to the shower wall and spread my legs like a slut as she covered me with soft soap from cock tip to balls and back to my ass. I was sexually spent but she easily got me to a semi hard state. I love having my semi hard cock stroked and when you add some anal play I am a happy guy. As my cock rose to full tumescence I had to stop her so I wouldn't cum. I reached out to move her from the spray so I could stroke that wonderful cock of hers. Now that she was completely naked I could see she had small titties with hard pointy nipples. As I was washing her fat cock I was sucking on her tits. I was now under the spray and turning to let the water wash away the soap from me. She was hard too and both wanting to prolong our fun switched to the other parts of each other's body. She was very soft and had no hair anywhere and I got lost washing her ass with both hands. I took the shower head down and spreading an ass cheek directed the spray to her butt hole. She helped by spreading the other cheek for me and my cock got harder just seeing that wonderful opening remembering how great fucking it felt. I thought I saw some of my cum wash out and it excited me. Hanging the shower head back up she started washing me and when she got to my ass she said: "You have such a hot ass! I just love it." She was working my cheeks over it so well and I just love my ass caressed. After a while she ran her fingers down my cheeks and lingered over my ass hole. I spread my legs and leaned into the wall as she played with my hole. Much to my disappointment she let go of my ass and said: "Give me a moment hun and I'll meet you in bed." I stepped out and after drying off went in search of her bed. Finding it I slid under her covers and easily drifted off to sleep. Sometime later I woke to the feel of someone caressing my ass cheeks. I was on my side facing away from her with my top leg spread forward giving her access to everything. As she was caressing me she said: "Do you shave love? You feel so smooth?" "Yes, I shaved everything before I came to meet you, do you like me this way?" I said flexing my ass under her touch. "Oh yes, but you should wax, it is so smooth and last longer." She adds. "Ah, I don't see me asking for a wax at a salon any time soon!" I laughed. "Oh, love I have someone who can come to you or better yet you can go to him. He is a gossipy little twink but you might get a BJ at the end and he can do it in his place. I'll give you his contact info." She tells me. As she caresses my ass she moves her hand over my hip to run her fingers down and around my semi hard cock. With my ass cheeks spread she moves her cock to rest between them as she runs her hand around my cock. She holds it softly and slowly strokes me while sliding her cock in my ass crack. As she runs her semi hard cock up and down my ass crack she says: "You have a wonderful ass love, do you think I might make love to it?" "You keep caressing it as you are and you might just get your wish." I say as she feels my cock come quickly to its full size. Spurred on by my desire to enjoy her attention to my ass she continues by spreading my cheeks wider and running her cock between them. She was stroking my neck with her free hand and whispering in my ear. "You have such a nice ass. I didn't realize how much I wanted it until I saw it in the shower. All nice and smooth, but so strong and manly. I am usually only a bottom but every now and then I want it all. When you let me fuck your mouth before you tried to fuck me you cannot know how hot that made me." She whispers as she concentrates on my ass as my cock is all but forgotten. Sometimes during anal play my cock shrivels up to its smallest size. But usually on the few occasions I am penetrated and relaxed it returns to its full measure. As Billi is enjoying playing with me it is shrinking and all my sexual energy is focused on my ass. She continues her kisses from my neck and down my spine as she is now rolling me onto my chest freeing up both of her hands to work my ass cheeks over. By the time she is kissing the small of my back she is really turning me on with her hands on my ass. I am not often a pure bottom but from the time I let myself go with someone who I lust after. She was immediately on that short list of ones I really lusted after as soon as I saw her. That is why I was so hot to have her use my mouth. Now I wanted to give it all up and welcome her into my ass. We were in the midst of a high sexual connection because she easily slid into being the active participant in this scenario. I easily slid into the submissive. I wanted to be penetrated, to be entered, to be fucked. I wanted my ass to be the center of my being for this. "Do you want me Billi love? Do you want to fuck me? If you want my ass show me how much." I plead, offering her what she desires but wanting it as much as she did. She was now facing my ass and as she spread my cheeks I could feel her hot breath on my anus. I raised my ass up almost begging for her tongue when she said: "Take that pillow and place it under your hips and help me make this wonderful for both of us." "You're a nasty, naughty boy aren't you? You are offering your tight little ass up to a girly boy. You are just another slut aren't you? Just want to get fucked..." Before she could finish I said to her: "Yeah, I am a horny fuck, but I only offer up my ass to the best, the hottest. I have fucked my share of guys but you are the first that I wanted to surrender it to. So, my hotness take what I am offering and make me forget any others." She squeezes my ass and runs her tongue from my balls to the base of my spine. I am completely at her mercy as I lay my head down and spread my legs opening myself up to her desires. She is quick to feel my surrender and continues to lick my ass crack. She knows her way around a man's ass and quickly brings me to a new level of excitement. I have offered the last of my maleness and she has taken it. I don't even think of myself as giving up any of my manhood, just being completely able to enjoy all the pleasure that one's body can experience when he has an experienced partner. She progresses from running her tongue the length of my ass crack to licking my ass hole driving me insane with lust. She covers my anus with her mouth and works it with her tongue until I want more. I want to be penetrated. Looking up I see the bottle of lube and reaching for it break her connection with my ass. Seeing where I am reaching she leans to meet my hand which brings her hot cock head into the cleft of my ass and it easily slides up my crack to come to rest on my ass hole. As she leans forward the tip of her cock presses into me opening me up. But due to her impressive size I cannot relax quickly enough to allow her complete entry. She knowingly feels me tighten up and quietly says: "Relax my love, I won't hurt you. I will make sure you are open enough to enjoy my cock. I know how to treat a nice ass like yours when it is offered." Using the lube to cover her fingers she takes them to quickly cover my ass hole. Gently running them around it she quickly returns me to my relaxed state and before I know it she has two fingers deep into me. She works them in and out of me as she crosses them and flexes them opening me up even more so that she tries to push a third into me. This is a lot more than I have felt in a long time and she realizes it and moves to stop. I tell her: "wait just a second and let me relax for a moment. When I take a deep breath fill me with your fingers so that I can accept that beautiful cock of yours." She rest her fingers around my anus and holds my cheek open with the other as I prepare myself for what is about to happen. "I am about as ready as I'll ever be, take me sweets." I say as I exhale and when I inhale she easily slides all three fingers into my ass. I feel so filled but know that this is just the beginning and after she is working me open she pulls her fingers from me and I feel so empty. This quickly changes as I feel her cock head touch my ass hole. My moan is all the encouragement she needs to push into me stretching me like I have never been. It should be painful but it feels so good! As she slowly fills me with her hot fucking cock my entire being is centered in my ass. I feel her being gentle with me and it makes it easier for me to accept her fat cock. She has the biggest cock that has ever entered me but I am aching for it. I feel her stop and then I feel her balls come to rest on mine I realize I have her entire huge cock inside me. She rest there and I remind myself to relax and enjoy this. I was so worried about not being able to take her girth that I forgot to enjoy it. Relaxing I stretch out my arms and legs and push my ass up trying to take more of her into me. Sensing that I am ready she slowly pulls almost out of my ass and when I try to open myself up for her she pushes back into me. We continue like this until I am relaxed enough to beg her for more. Having taken all the cock she has all she can do is speed up her fucking of my ass. She is now laying forward on my back and softly talking to me saying: "Your ass feels so good love. You are so wonderfully tight. You are more man than any before you because you are the first to take all of my cock and reach for more." I squeeze my ass and she says: "Oh my fuck, stop that, you are so tight that I cannot take much more of that!" It is now that I realize that my cock is very hard and uncomfortable under me so I reach down to move it to rest along my stomach. I almost cum from just that slight touch. I want her to remember the man who took all of her cock and wanted more so when she pulls back I squeeze her and just as she reaches the end of her stroke relax and open myself up as much as possible begging for more. She moans and bites my shoulder as she pushes back into me. We fuck like this lost in our shared pleasure. I can feel her balls tighten up and come to rest close to my ass hole and this pushes me to the edge. I want her to cum with me as I am so close. "Cum with me baby, shoot your hot load into me and fill me with it as I cum too. Let's cum together so we both remember this night. As she grabs me by the shoulders she speeds up her fucking. God it feels so good and as I scream: "I'm cumming baby, cum with me! Fill me with your cum!" And slamming her cock as deep into me as she can she holds me and I feel the heat of her cum shooting into my guts. After a couple of intense shots she moves back to fuck me as her balls empty themselves into me. I feel my own balls tighten up as they shoot their load out my throbbing cock. The motion of our coupling is enough to bring my orgasm on and I cover the pillow under us with my hot sperm as she does the same with my insides. She slowly stops and runs her hands down my sides to reach under me and find my cock with one hand to stroke it and the other to squeeze the last few grams of cum from my balls. When she feels that I have been drained she pulls her cock from inside of me and this is so incredible I cum a little more and surprised she milks this from me. "Wow baby, I didn't expect that. Did you cum twice for me?" She asks. "Once, twice, I am so high on your cock that I just don't know. I do know that what we have done today is more exciting than anything I have ever done." I say to her meaning every word of it. As we lay side by side coming down from the experience I hear a door opening and being unsure of what to expect have to ask: "What was that? Is someone here?" "Relax love, that's just Mia, my roommate coming home. You will like her." Billi says looking at me with a smile. "What is she like? Is she..ah...like you?" I query. "Do you mean does she have a big cock like me?" seeing my embarrassed nod she says: "No, well, maybe not quite as big, but the boys we play with have always been happy." "Why, wasn't I enough for you?" She questions. "Oh my sweet you were plenty, but really, what would you say if we were at my place and a friend of mine arrived?" I ask ...the rest is to be seen...