It finally happened, I got fucked in the ass and loved it.
I'm 55yr, white, married, business man type (kakis and a golf shirt type, not a suit guy). I have a good sex life at home with my wife but occasionally crave sucking a nice cock and taking a load down my throat as I have been a closeted bi guy all my life. I used to be able to go to the M4M section of Craigslist and have some local hook ups, but since CL closed down the personal adds, and the local wild fires burned up all the cruisy parking lots and bushes, finding a cock to suck has been a lot harder to do.
A few months back I discovered a Thai Massage in the San Fernando Valley area of LA that has Ladyboys that I have begun frequenting. This has been really fun and typically consists of them starting out with me naked face down on the massage table then them massaging my legs and working up to my ass then reaching around to my balls, then I turn over. The routine has been for them to take their panties off, slide up over my face and feed me their cock and sweet asses, then 69 until they shoot down my throat. Don't get me wrong, I have had some hot times and may go back and write some stories about those adventures, but that was not what happen yesterday.
Yesterday is stopped by my favorite massage place in the valley and was greeted by a little Asian girl asking me if I had an appointment. I said, no..... and she asked if I wanted a girl or a TS. I said quietly.... a Teee... she says, TS? ok, you sit down I be right back. I take this time to use the bathroom right there and take a leak and when I came out the little Asian lady (she looked like she was 10yrs old, I found out later she was 30yrs old) says, ok, you follow me. Have you been here before? I said, yes, lots of times.
She leads me to a room and I stripped and layed face down naked and waited until there is a knock on the door. Usually they walk in after that, but this one knocks again, so I turn to my side and say... come innnn..... and in walks a tall thin black TS that I have never seen before. Very pretty with big tits and a really thin waist down to a skinny butt, skinny but a small bubble ass, wearing a tight skirt. I layed back down and she asked about the tattoos on my back as she gets a wash cloth and cleans my body with the damp cloth. It feels good on my back and ass cheeks, then she takes the cloth in to my ass crack and roughly wipes it in my ass, turns it over and cleans my ass again. I'm very meticulous about wiping my ass so I know it couldn't have been that bad.
She settles in to rubbing my legs up to my ass, then back down my leg and up the other leg to my ass. She did this for a while and I started to relax and I gently slide my legs apart. She continued on my ass and was doing some amazing things with her thumbs just below my asshole and I was starting to squirm on the table and pooching my ass up letting her know how much I am enjoying this.
Suddenly she left the room, then came back with another washcloth and wipes in my ass crack again. I'm thinking, she must be getting ready to eat my ass...... oh man, this is going to be great..... but instead, she goes back to massaging all around my ass, then reaches under and starts feeling my balls. I raised up on my knees and push back in to her and feel her hard cock in her panties press against my ass and she gently reaches around and strokes my cock.
She backs off and I turn over. She grabs my knees and pushes them up and puts her panty covered cock to my ass and starts slowing pumping as she squeezes my nipples and looks down on me with big dark eyes that are smoking with lust. I reach up and squeeze her tits that feel real but are probably some expensive breast forms but for now they are real and beautiful. She puts my legs down and slides up on my chest and pulls her hard cock out and starts sliding it around my lips, taping it on my lips but not letting me get it in my mouth as I stuck my tongue out and strained my neck up desperately wanting to get her cock in my mouth. Finally she stops teasing and slides it in my mouth and I let out a moan of pleasure as I get what I have been craving, a nice shemale cock. I feel her ass and pull her cock deeper in my mouth and can feel it grow and strengthen. It was about 7" and not super fat, just a nice manageable cock that fit perfectly in my mouth and throat. She reached over and grabbed a pillow and slid it under my head that propped my head up, then really started to face fuck me. I'm thinking, oh man this is fucking great, when she suddenly pulls her cock out of my mouth and bounds off the massage table.
She grabs my legs and spins me on the bed sideways and steps between my legs pushing my knees up. Leaning down over me and kissing my neck and biting my earlobes, pinching my nipples hard and whispers in my ear........ what do you like daddy?... I choke out.... uhhhhh I like to suck your cock and eat your ass, then take your load down my throat and swallow what you have. She says..... mmmmmmmm that sounds hot...... but not today. Today.... I'm going to fuck you. Your ass is mine. Do you want that daddy? All I could do is nod and she says, what was that? do you want me to fuck you? and I said out loud, ..yeah...... fuck me...
She grabs the side of the massage table and pulled it toward her which allowed me to put my feet against the wall. She reached over to a table and grabbed a condom and some lube and slid it on, then applied some lube to her cock and my ass. I have had 3 cocks up my ass before and all of them lasted about 3 or 4 pumps before I said it hurt too much and squirmed out from under them, so I have never truly been fucked. So here I am looking up at this tall thin black TS with my ass hanging off the edge of the table as she lines up her cock to my asshole. I think, ok.... and feel the head of her cock press against my ass, then she pulled back and grabbed some more lube, this time sticking her finger or two (I couldn't tell) in my hole as she applied the lube.
She jacks her cock a few times to get it back fully hard and lined it up with my hole again. This time I felt the head pop in then slide in a few inches. She stopped and let me adjust. I tried to relax but it hurt. It hurt on the edges and it hurt on the inside.... as she slowly started to pump in and out. The pain started to lessen and she started to pump harder. She grabbed my legs and pushed them off the wall and up to my chest, looking me in the eyes she just started jackhammering in to my virgin ass. I could feel our tail bones banging and hear the slapping. I moaned and put my head back.. It still hurt and felt uncomfortable when she stepped back some and slowed down. She reached down and started slowly stroking my cock with her oily hand and she steadily fucked my ass. I'm not sure how long this fucking and jacking my cock went on but I zoned out and totally relaxed and enjoyed what was happening. I came back to reality and noticed that it not only didn't hurt anymore, but it felt amazing, almost euphoric and I didn't want it to stop. I was moaning and telling her how good it felt.... when just like that with little warning I was ready to cum. I tried to hold it by grabbing her hand but it was too late and I screamed out, ohhhh I'm cumming.... and shot a massive rope up on my chest then shot after shot and she continued to fuck my ass and pull on my cock.
I felt like I was going to pass out but my cock was now so sensitive that I grabbed her had and made her stop when she leaned in and buried her cock all the way in my ass pressing me down...and I feel her cock pulse and she fills her condom in my ass. We stayed like that for a minute or longer, I lost track of time, until she slowly pulls her cock out of me and helps me slide back on to the bed. I see her pull her cum filled rubber off her cock and drop it in the trash can, finds her panties and slides them back on, pulls her skirt back over them and says, I'll be right back. She was gone for a few minutes and I just layed there, totally spent.
She came back in with a warm washcloth and cleaned up my cock, then lifted my leg and cleaned my ass. As I layed there spent, she asked..... are you ready for you massage now? I said, no..... I have to go, I heard my phone get a message. .... but she kept rubbing until I couldn't resist. She went on to give me the most intense massage I have ever had. So I sit here this morning with sore muscles from her massage and a sore ass from that amazing ass fucking..... trying to figure out when I can sneak out and do that again.