This is a 100% true story that just happened 2 weeks ago, and I have not stopped smiling since.

I'm 26 and consider myself mostly straight, but you would probably call me bi. I've been into trans women for about 2 years or so now, and also have a thing for femboys. I've been with two trans women before, but only received oral, and never had sex. That all changed recently, when I was fucked senseless by a beautiful trans porn star.

About two weeks ago I had plans to hangout with my ex gf over the weekend. We dated years ago, and have remained on again off again fuck buddies since breaking up. We don't have much of a real connection anymore, and have somewhat of an unspoken understanding that it's just about sex. This all honestly made it a lot easier to flake on these plans, when I noticed one of my favorite TS pornstar's (**I'm going to call her J)** posted on her twitter that she was coming to my city that Friday. "Holy shit...no way", I thought, is this something I'd actually consider? I knew this meeting would require a donation, which is something I would have never ever have done before. I wouldn't actually do that would I? ...Fuck yes I would. I put any pride aside and admitted this was an experience I wanted.

I texted my ex to break the plans, told her I wasn't feeling well. No questions asked, and I was now in the clear to try and set up my date. I texted the number provided on J's ad, and had a response back within the hour. She asked me a few questions to vet if I was serious, and I sent a pic to expedite the process. After a brief back and forth, we made plans to meet at her hotel Friday at 9:00pm, and it was currently Wednesday. "Should I bring anything?", I asked her. "Weed and Wine if you like" she added with a kiss emoji. I was shaking with excitement.

Friday night rolled around and I began to get ready for her. I have always had a thing for wearing thongs and jockstraps, and was elated to have a chance to put them to good use. You could call it somewhat of a fetish I guess, nothing too kinky, I've just always loved the feeling of wearing them. After showering and shaving I laid a few options out on the bed. A red thong, a black thong, a red and black sporty jock, a blue Hawaiian style fashion jock and a black leather jock. So many choices, so hard to pick, but I went with the red and black jock. Still torn by the other great options, I threw them in my bag as well. Maybe things would get a bit messy, and I'd need something to wear afterwards.

It was now time, I texted her for the address, got all my things together, and hopped in the uber. When I arrived at the hotel she texted me her room number, top floor in a very large hotel. I found myself shaking with excitement again in the elevator, as I watched the numbers tick by, it felt like an eternity. As it finally hit the top floor, I took a second to catch my breath and stepped out of the elevator. "Left foot, right foot...you fucking got this", I tried to reassure myself and I felt my palms racing with sweat. I dried them off on my jeans while I walked, finally reaching her door at the end of the hallway. I knocked, she answered, I stepped in, and my fantasy began to turn into reality.

"Hey sweetie, nice to meet you" she said and she stepped in for a kiss. We kissed a few times as we embraced each other in a hug. She was wearing just a bath robe and smelled amazing. She grabbed my hand and lead me to the bedroom, as I put my bag down, took off my shoes/jacket and started to get comfortable. She poured us both a glass of wine from her open bottle as we both laid down on the bed and started in with some small talk. As we get to know each other we eventually kill the bottle, she asks to get the donation out of the way. I say I was hoping for 2 hours of her time, and I complete the process. She wastes no time after that and begins attacking my face, kissing me passionately and shoving her tongue deep into my mouth. I was taken a bit off guard, but I loved how she took control. Quite literally wrestling her tongue against mine, while she rips my t shirt off of my body. After she pulls my shirt over my head, she pulls me on top of her and looks me right in the eye. "Are you a top or bottom?", she wastes no time asking.

"I"ve only had sex with ciswomen, so top I guess? But I.." I began explaining, but she cut me off.

"What about this? You interested in this?" She boldly asks as she unties her robe, signalling me down to look between her legs. I look down and see a beautiful bulge, covered by a pair of silky black panties. She rubs her bulge slowly, squeezing it just enough to accent the outline of her rock hard cock. "Yes...very much so.", and shyly say back to her with a nervous smile. "Good answer sweetie..why don't you give me a nice kiss down there?", she says back to me in a sexy but powerful manner. I happily oblige, starting at her tits and kissing my way down her stomach, until my lips have met her the tip of her bulge, now wet with pre cum.

"You haven't done this before, have you", she accurately asks me. "No..I haven't", I admit. "I can tell", she says as she slowly runs her fingers under my chin and across my lips. "Such a nervous boy...tell me what you want to do," she gently commands. "I want to um..suck you off", I quietly utter, face turning beat red no doubt. "It's okay babe, tell me. It's our secret," she reaffirms me with with a sly smile, certainly enjoying how nervous I am. "I want to suck your cock, give you a blowjob", I say as I slowly run my tongue up and down her panty covered shaft, shifting my tongue underneath her panties the end, to remove the throbbing member from the silk pouch. "Mmmm, that's such a good boy", she says as she begins to run her fingers through my hair, softly but firmly gripping the back of my head. I start slowly, but eventually she begins guiding my head up and down in a steady motion, pumping her cock into my mouth.

"Breath through your nose baby..you're doing such a good job", she encourages me. It has not even fully hit me yet..but I have a cock in my mouth. Not only that, but I seem to have taken it up quite quickly, because before I know it, my lips are completely kissing the base of her pelvis. I went from never have touching another person's dick, to having one punching my tonsils over and over. "You are a natural baby..I can tell you've wanted to try this for awhile." Guilty.

After giving her my throat for about 10 minutes, she pulls my face up and slaps me in the face a few times with her dick. "Mm..you love yourself some lady cock, don't you boy?", she asked me in a playfully teasing manner. I love how she called me 'boy', it made me feel submissive, and like she was the teacher in this situation. I think there is only a 6 year age difference between us, but I wanted to play into the role of being a younger 'boy toy' type, a plaything for her to have.

"Yes, ma'am", I said as I rise up off her cock, starting to undo my belt. "I love women like you", I proclaim as I slide down my jeans, revealing the front side of the red/black jockstrap I was wearing. Her eyes light up and she gets a sight of the sexy underwear I chose. Getting up and stepping forward she says "mmm..lets fuck!", reaching between my thighs and grabbing a tight grip on my bulge. As we begin kissing again, we wrap our arms around each other, running our hands across one another backs, leaving scratch marks in the process. She only saw the front part of my underwear at first, and must have thought they were briefs. Because when her hands made their way down my back, to the top of my strap and across my bare ass, she broke off the kiss and gave my ass a very tight squeeze.

"Oooohh a jockstraaap!", she shouted, giving my a wink. She slapped my ass twice with both hands and then grabbed me on the shoulders. "Turn around! Let me see this thing!", she playfully said, while forcefully twisting my shoulders, and pushing my towards the coffee stable in front of me. Not gonna lie, I felt a bit man handled here. And I'm not a small guy, around 6'0 180lbs and in average shape. But regardless, she was in control and I loved it. Luckily, I kept my balance by placing both hands flat down on the coffee table. "Cute! White boy has a nice bubble butt!" (she is latina), she said with a laugh, giving both my cheeks another squeeze. I was at a total loss for words, all I could do was smile. Smile so hard, I thought my face was going to cramp. I was loving every single second of this.

"Anyone with these cheeks, and a jockstrap, is a bottom baby! You wanna be my little bottom boyyy?", she teasingly cooed in my ear, pressing her throbbing cock up against my virgin ass. "Yes mommy..please show me what to do," I begged. I was hers to own. All of a sudden, I felt a warm sensation between my ass cheeks. I look back, and see her beautiful eyes staring up at me, splitting my round globes with her tongue. I felt like a cat in heat while she licked me, getting my virgin ass ready. Eventually the tongue turned into a finger, then two, then three, as I was biting my lip so hard I thought my teeth were going to crack. "You're ready...I'm going to fuck you," she said as she slowly stood up.

I sensed her raising up to her feet as her fingers remained in between my cheeks, still rubbing my hole. Soon both those hands found there way around my body, squeezing my pecks as she pressed her cock against my bare ass, exposed by my jockstrap. "How do you want it...what position should I fuck you in?", she whispered in my ear, running her tongue up and down my neck. "Um..doggystyle. Will you fuck me doggystyle?", I asked, like I was needing permission. "You want me to bend you over, and fuck you from behind? Do you want your face in a pillow..while I pound you in the back?", she asked in a serious tone. I was aching for it, hearing her say this out loud, what she was going to do to me, and making me say it, I was leaking on the spot. "Fuck yes..I want you in me. Please pop my cherry", I begged.

She moved to the bed and placed one hand between my shoulders, pushing my chest down. With the other she grabbed my waist and propped it up, with a few slaps of her cock between my cheeks, she wasted now time, and began lining up to get inside me. My ass had a mind of its own, and it knew what it wanted, because she slide inside me with complete ease. No more than three pushes, and she was inside my ass, a virgin no longer. "Oohhh my godd fuck! Mmm what the fuck?!", was all that I could manage to say. I couldn't believe how good this felt, so..fucking...good. There was some slight pain at the beginning, but honestly, it was not that at at all. Tingles and bits of ecstasy were running all over my body, as I no longer had any control of what I was saying or doing.

"Fuck! Oh my god yes! More!"

"Mmmm...soo good God fuckk give it to me!"

"Why does this feeel sooo gooood?? Fuck me mommy!"

Those are some examples of what I was screaming at the top of my lungs. It was almost like an out of body experience. I wanted to stop saying those things, I truly did. I can remember saying to myself, "shut the fuck up, you sound like such a fucking whore right now", but it was no use. She had me face down, ass up, begging for as much of her lady cock as she could provide. She then grabbed the back of my head, pushing it into a pillow, and went into turbo mode.

"You want mommy's cock? Are you my little bottom boy?", questions she clearly knew the answer to.

"mmmmyesss!", my shout was muffled, because she was pressing me face down into a pillow.

"I can't hear you. Do you want my cum?", she asked and she pulled me by the hair, releasing my face from the pillows grasp.

"Yes please! Cum with me!", I desperately pleaded, rock hard and ready to release.

"Where do you want it? Where do you want me to cum? You want it on your face, don't you?", she confidently asked.

Guilty. Guilty as fucking charged. I wanted it, all over my face.

"I knew it", she said with a laugh, pulling her cock out. I squealed like a little bitch as her cock slide out of me. But next thing I knew, she flipped me over on my back, and scooped up my legs like a power bomb from a WWE wrestler, and threw them over her shoulders.

\*SLAP\* \*SLAP\* \*SLAP\*

The sound of her thighs clapping against the back of mine, and she furious pounded away at my inside. I couldn't take it any longer, and I gripped my dick as hard as I could. "Oohh my god fuckk, your fucking making me cum!", I wailed out as she continued to impale me. Cum shot up into the air and all over my stomach and chest. With every pump against my prostate, more streams jetted out as I was soon laying in a pool of my own cum.

"Cute baby...now it's my turn. Open your mouth,", she said with slight warning. She pulled off the condom, slipped herself between my lips, as my moans quickly turned into gags. I was now face to pelvis, as she pumped her cock in and out of my mouth. I've never felt like more of a slut in my life, laying there covered in my own cum, with tears, spit and pre cum dripping down my face. "Close your eyes!", she shouted, as she forcefully pulled her cock out of my mouth, flinging spit and precum across my lips and down my face. "Here you go baby!!", she shouted, as the hottest splash I've ever felt in my life erupted across my face. And it didn't stop. Every bit I licked up was quickly replaced by more cum. Warm and slick, and laid there taking in her moans, as she rubbed the remains out on my tongue and slowly painted it across my face like a brush.

"That was so, fucking, hot. Wow..you're fun," she said as she hopped off the bed. "Jesus christ..let me get you a towel."

I laid there on the bed as she washed up, in absolutely bliss. My biggest fear was that I would regret this as soon as I came. That I would never be able to look myself in the mirror again. What happened was the exact opposite, I was so happy. I finally acted on my desire, and I loved it. I just laid there hoping this moment wouldn't end.

I was in such heaven, I didn't even realize I had been laying there for 10 minutes. Long enough for her to take a quick shower. My moment was interrupted when I felt a towel quickly land on my face. "Sorry, I wanted to wash off real quick. Have you just been laying there with cum on your face...?", she asked with a raised eyebrow.

I was pretty fucking embarrassed. No reason why I should be, I literally just had this women's cock in all my holes just a bit ago, but her calling me out made me blush like no other. "Um yeah...keeping it as a souvenir...", I lamely joked back.

"Haha oh my god, you're cute!," she said to me with a smile, looking over her shoulder while she brushed her hair.

Fuck, me. I've never felt like more of a simp in my life. And you could call me that, and I couldn't argue. I literally funded this experience, but I didn't care, and I don't now. I was reveling in her affection.

"You brought weed and more wine right?", she asked with her back turned to me. I did, but I had also just considered the time. I had almost been there for two hours, and I was afraid my time was running up.

"Yeah I brought both", I assured her. "Cool, you can stay the night if you want", she offered nonchalantly.

I kept my cool, "Oh really? Yeah, I'll stay over", masking my excitement to not seem desperate. Inside I was dong backflips.

"Nice. You should open the bottle and roll something up", she said. "Gladly", I answered as I rolled off the bed. As I stood up, I realized what a sticky, cum covered mess my jockstrap was. I grabbed the sides and slid it off, as I stepped one foot out of the strap, and she walked by and gave my ass a smack. "Shame we made such a mess, that looks cute on you", pointing at my love covered jockstrap.

"Oh haha I have others!", I exclaimed, probably a little too enthusiastically.

"You do? You little hoe! Let me see!", she said with a playful slap to my chest.

I loved when she teased a bit like that, and she could tell. I was putty in her hands. As I walked over to my bag, I could feel her eyes gazing upon my ass. I got goosebumps feeling so exposed. I pulled out the thongs and jocks I brought, and laid them on the bed for her to pick.

"I like the red one", she said with a wink. The one she picked was a shiny red t-back thong, with a slit that opens in the front of the crotch. As I stepped into and slide the thong up, she grabbed the straps and pulled them high on my waist. \*SMACK\* she let go of the straps and they slapped against my waist, splitting my ass perfectly in two.

"My little thong boy. You're not wearing pants for the rest of the night, by the way," She said with a playful smack to the cheek. Fine with me. I had my order, it is was to be her play thing for the rest of the time I was here.

I began to break up and roll up my weed, as she started to open the bottle of wine. "Oh, you don't have a cork screw?", she asked. I didn't, and the bottle we drank before was a twist off. "That okay, I will ask room service," she said. Simple enough, she made the call, and I finished rolling up a joint. Right as I finish rolling it, we hear a knock at the door. It's room service with our cork screw, and she asks if I can answer the door.

As I get up and begin to put my pants on, I hear her protest. "Ahh ahh ahhh, remember what I said...?No pants mister." Was she serious? Did she really want me to answer the door, wearing nothing but my red thong?

"Are you..for real? You want me to..", I say with a nervous laugh, but she cuts me off.

"Yesss for real, don't be shy baby!", she says with a wink and a laugh. Wow, okay. As I walked to the door, I felt myself getting hard. This stranger is going to see me in nothing but this skimpy thong. Why am I getting hard, when did I become such a hoe?

I open the door with a forced smile as I'm greeted by the middle age house keeper. She gives me the elevator eyes quickly, tries to hide and smile and says "Um..you asked for a cork screw..?", she manages to say. "Yes, thank you very much," I say as I grab the screw from her and toss it on the counter, trying not to move too much and expose my back side. As I turn to close the door, we make eye contact again and I see her take a glimpse at my cheeks, split by the thong. I was not attracted to this women, at all, but I was to the moment. Something about being so exposed and vulnerable, walking around like a piece of meat on display, I loved it.

We drink a few glasses each, and decide it's time to spark up the joint I rolled. We make our way to the bathroom, run on the fans and put the shower on full blast. As she is walking around lighting candles, she takes off her robe, revealing her silky black thong. With no hesitation, she then strips the thong as well and turns to me, cock completely exposed. She catches me admiring her meat and says "I think I know something else you want to smoke too." Once again, guilty.

As we go about smoking the joint, drinking the wine and talking a bit more, I keep trying to sneak glances at her impressive shecock. Eventually, she grabs my hand an moves it right against her crotch, placing her rock hard dick in my hand. "Do you want me to cum in your mouth," she boldly asks. Straight to the point, didn't even bother asking if I wanted to suck it, because my eyes did all the talking for me.

"Yes...I want to swallow you", I said with the most confidence yet all night. She gave me a deep kiss, took my hand and walked me back to the bed room. I wasted no time and went right for it, quickly engulfing her cock in my mouth and down my throat. I went to town for what must have been at least 20 minutes, using every trick I've seen in porn and had used on me. I was bobbing up and down like a cheerleader on prom, and was loving every second of it. I finally came up to gasp for air, and as I opened my mouth a fountain of spit and precum cascaded down my face and onto my chest. I grabbed a handful with my left hand to use as lube, and started furiously jacking off, while using my right hand to guide her cock back in my mouth.

I lasted maybe all of 3 minutes, before I shot my load all her stomach. She used her hand to get the rest of the cum out of me, and instructed me to focus solely on her cock. I began to use two hands to pump, one fist on top of the other, whole sucking like my whole life depended on it. I could tell I was close, as I began to feel small jets of cum shooting into the back of my throat. \*SMACK\* \*SMACK\* I yelped with her cock still in my mouth, as I felt two swift spanks on my bare thong covered ass. "Yes, Yes, Yes, I am so fucking close!", she shouted. "I'm cumming!" \*SMACK\* She shouted, while simultaneously giving me another smack on my now very soft ass.

I have to give myself credit, I swallowed every last drop, and made sure everything was cleaned up after. I licked, sucked, kissed and detailed every inch of her dick until it was soft again. I laid there with my face in her lap, enjoying the after glow of the epic oral I had just given.

"Oh my god...that was so good baby,", she said, taking a few deep breathes.

"Really? Did a goob job?", I asked. Shamelessly seeking more approval.

"Yes...such a good boy. What're you doing tomorrow?", she asked, catching me off guard.

"Um I'm not sure, no plans I don't think", I said, trying to keep it cool.

"Well if you want, you can come over again. I have the room for another night", she offers.

"Yes", I say immediately.

"Cool, that'll be fun. Come here," she instructed me, softly gripping my hair and pulling my face up from her lap to her face. "Rest your head here, and suck", she lovingly requested, pressing my face against her tits.

And that's the last thing of the night I remember, falling asleep while laying on her chest, like a fucking baby. We woke up in the morning, and that is where part 2 of this story will continue.