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My Foggy Late Night Story
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Add: 4 March 2016 / 00:00
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It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do anything, including exercising, which was another problem I had to deal with since I hadn't exercised in nearly a month.
I looked at my stomach in the mirror. I couldn’t believe it. I felt like I was gaining a bit of weight.
"Fuck!" I said to myself out loud. "My tummy feels bloated! I need to get in shape again. I'll wake up early to go running."
Normally, I would wake up before 5:00 am to do some stretching before running. I usually dressed in men's workout attire on weekdays. On weekends, however, I'd change it up and exercised in my female attire, dressed as Sasha, my feminine alter ego. It had been that way for about a year now.
Currently, I live in a quiet neighborhood about five miles from my junior college. I moved out of my parents' home for my own sanity's sake. I have a job, a girlfriend (who is completely unaware of my crossdressing, and would like to keep it that way), and also loads of free time to be the girl I that I am inside in the privacy of my own home.
I live in a small in-law studio adjacent to the main house. The family I'm renting the unit from are very cool with my personal life. They pretty much don't care what I do or who I bring over, as long as I keep it quiet and pay the rent on time. Fair enough, right?
The back door of my studio unit leads me to the running trail. That's where I always start my morning jogging routine. I'll admit, the trail is a very lovely place. You could run as far as you like to enjoy the scenery, the tree tunnel, and if the mood strikes you, you can go to a certain area about a mile away from the trail path, where some go to have a little “fun”. I attest to this because I have gone there a few times with my girlfriend when she stayed over. When she didn't, I would go and have a few encounters with other people, if there were any available.
Three weeks ago, I had an encounter with beautiful, older woman. She was curvy, petite, and in her early sixties. I swear she looked not a day over forty. She had ginger red hair and almost no wrinkles on her face. She wore a black tight sweatshirt and leggings. While we were passionately making out, she stripped down to just her purple thong.
I bent her over, moved her thong to the side, and pushed myself into her pussy. All throughout our morning of sex, she acted like a woman of twenty-five; the way she pushed her soft and spongy butt back and forth at me with such force and passion. It was more than I could take. She cried out for me to come inside her. We remained in a doggy-style position until I filled her up nice and good.
I also had chance encounters with a couple of guys when I went out as Sasha though they were individual spontaneous encounters. I will admit that I had considered having a threesome if that moment came around.
I always fantasized myself being in a threesome like this: I was on all fours, wearing only my bra and thong panties with my ass up and one guy behind me as he is sticking his thick cock through a slit I cut open on the back of my thong. I have another guy lying in front of me, legs spread, completely shaved with his dick in my mouth while I suck on it good and slow.
While he watches me get pounded by my other lover, he begs me to let him fuck my ass after the first guy dumps his hot load inside me. After the first guy unloads himself in me, the second guy comes and shoves his hot dick and fucks me harder until he comes inside me.
Damn, I want a guy in my ass so badly, I thought to myself. That fantasy made me hot and horny, I couldn't help myself but jerk off until I shot my own load all over me.
Seconds later, it hit me. I thought to myself, Why wait to run tomorrow morning when you can do it now?
Sure. It's a great idea, but it was nearing midnight. Who knows what kind of people are out there this late at night. Not to mention it was a late Friday night, and it was really foggy. Some psycho could be prowling for anyone. I could get into a lot of trouble, yet it actually made me want to go out and do it more. Yes, I was still horny, and, yes, I also needed to get some exercise. While I thought these things, I noticed a few running out late, too. So, I figured it was safe. I hadn't heard of any recent incidents that involved defenseless people running in this trail. The only real risk I took was getting caught by a ranger or police for violating a park curfew.
"To hell with it!" I said. “Let’s do this. Sasha is in the mood for fitness and some fun!" But, before anything, I went off to take a shower to clean off all my cum after I let myself go crazy in my own daydream.
After my shower, I got dried up and pulled out my running clothes. Since it was foggy, I needed to wear something bright so that I could be seen in case someone bumped into me while they were running. I put on a special white workout thong with a gaff that pushed my nether regions in. I cut a slit on the back of the thong before I put it on.
I also wore a black workout bra with my silicone breasts to give myself a slightly busty look. Then came my white fleece pullover, white flared bell-bottom yoga pants, and my socks and trainers. Of course, I didn't forget to put on a bit of foundation and lipstick, and a small black wig. I was ready to go!
I decided to take a spare thong in case of an emergency, and I put it in my fleece top pocket.
So, there I was, about half a mile already in, and it was ten past midnight. I was out jogging in this cold, wet, and foggy Friday night, and I was thinking how the hell was I gonna get lucky this late at night? There was nobody around, and I began to feel stupid and scared. And pretty soon, I would get into trouble. What would happen to me? And what would my family and girlfriend think when they heard that something happened to me in this trail?
Or worse, what if I had been caught dead dressed as a girl? Well, firstly, they would say: “Why did you go running this late at night?” Secondly: “Why in the fuck did you dress as a girl?" Oh, boy! If that happened, and I survived whatever accident it was, I know I wouldn't hear the end of it from my parents. In my girlfriend's case, it would be the end!
Dammit, Sasha!, I said to myself. You could get into a lot of trouble now. Let’s turn around and go back. That was enough for one night.
Yeah, fun indeed.
Before I could turn around, I heard what sounded like footsteps. And they were getting louder, and faster. Oh, shit! I wasn't going to turn back. In my mind, I thought that this was it. If something were to happen, better I wound up dead after it. My heart was ready to jump out of my throat as the sound of running got louder. And then, slap!
"Wake up, girl!" a middle-aged black man yelled as he slapped my ass. It hurt!
"Ouch! You dumbass!" I yelled.
Suddenly, he stopped. I thought: Oh, shit! He’s gonna kick my ass now!
He walked back and stopped in front of me and said: "Look, bitch! You was in my way. Now, I could’ve just ran into your hot ass and hurt you, or just move to the side and give you a heads-up that I was running and smack your hot ass. Either way, I was gonna hit ya!"
We glared at each other for what seemed like an eternity, only for him to kill the mood and yell: "WHAT?”
What? What, what?, I thought. I couldn't say anything. I was still in a terrified state. I just looked down. "Sorry, man," I said in my raspy, timid feminized voice. "You just caught me off-guard."
"Hey, it's cool. Shit like this happens all the time. Just gotta watch yourself, baby. What if it was some wacko who wanted to rape you, only to find out you are a dude in girl’s clothing? Then, you better pray hard that he don't kill you!"
Eh? How did he... how did he know?
"You’re shocked because I said that, huh? Because I knew you’re a crossdresser?”
I mumbled out a, "Yeah, little."
"Don't worry. As far as I'm concerned, they are women, too. Only, they still have a dick. It’s nothing to worry about," he assured me.
I chuckled. "Thanks."
"So, what's a cutie like yourself doing at this hour?"
Stupidly, I responded, "Would you believe, to exercise?"
"Damn, girl. You don't have to be so rude. It was just a simple question."
I felt bad.
"Sorry, man. I'm just a bit nerve-wracked from your hard slap on my ass. But, yeah, I just needed a bit of fresh air. Trying to get back in the groove of things."
"I heard that. You and me, both. My wife is trying to push me to get some exercise, too. Can you believe that?"
"Hey, she loves you. That's important," I replied, giggling with him.
"Good thing my wife is pulling a half graveyard tonight, so I wanted to prove to her I got some running done today. She checks my pedometer every day."
"Really?" I asked. "Why?"
He said, "She's a nurse. Plus, she checks my glucose levels every night just to make sure they're normal."
Wow, I guess he was diabetic. That was the only thing that came to my mind. I didn't want to ask him, though. Then, he got closer and put his hand on my ass, which sent my blood rushing from his touch.
"Sorry, I hit you so hard," he said as he began to massage my ass cheek. I felt so hot with lust, and a bit nervous at the same time. I didn't know whether to let him keep groping me, or scream bloody murder. But, I reminded myself why I came out. To be fit, maybe not now. To get lucky? Well, hopefully.
"It's okay. It doesn't hurt so much now."
"No?"
"Nope," I said. "In fact, I kind of like what you're doing to my ass."
"Do you? You like getting your ass groped like this, baby?" His touch suddenly got a little rougher. I was enjoying it. I let him know that after I let out a little "Ohhh" from out of me.
"Damn. You transvestites and crossdressers sure know what you like," he said, all while he grabbed my ass harder.
"Yeah? You know what we like?" I asked him in my sexy voice.
He got behind me, placed his hands on my thighs, and whispered in my ear, "Yes, sexy. I know what you t-girls like. And I know you want it badly."
He started to peel my bellbottom yoga pants down to about the middle of my ass, exposing my white thong. He pulled my thong up a little bit, giving me an unexpected wedgie. It felt so good getting my thong pulled up like that. I leaned my head back and asked him to do it again.
"Pull it up, you dirty boy!"
As he pulled it up again, I felt my asshole burning. It felt so good, I begged him to do it again by pushing my ass against his hard cock.
"Damn, you are getting really freaky now."
"You started it!" I said accusingly.
"I know. And I will finish it," he said, as he gave my thong one hard pull that made me squeak.
"You better finish it, or I will be on your ass all night until you do!" I threatened.
I moved my hand down towards his bulge that was just urging to pop out of those pants. I unbuttoned his fly and pulled out his long dick, already wet from his pre-cum, and started to stroke it from behind me.
Through the fog I spotted a tree wide enough to hide ourselves in so that nobody saw us. I pointed to the tree and said, "Let's go over there. I want to suck your cock behind that tree."
"Sure," he whispered while he rubbed his cock against my ass crack. Oh, how he was itching to get it inside me. I wasn't going to let him just yet.
Once we got to the tree, he grabbed me from behind and started teasing me with his long cock moving up and down my ass crack. I responded to his tease by moving my ass up and down on his dick. He slapped my ass hard, causing me to moan. He would slap it again, and again. I loved it. I wanted more. He turned me around and pushed his mouth against mine. We started French kissing so passionately, slobbered our mouths to our heart’s content, all while he was grabbed on my ass cheeks, and pulled my thong up my ass harder and tighter.
It sent more shockwaves throughout my body. I moaned really loud into his mouth. He slapped my ass harder. It was hurting so much, but it hurt so good. After about four minutes of passionate kissing, I got down, pulled his pants down and grabbed his nine incher and just started to lick up and down his shaft until he forced it into my mouth. Man, his cock tasted so good. I bobbed my head back and forth a little faster, and the harder he got, the faster I sucked him.
He seemed to enjoy that a whole lot.
"Fuck me, you have really been wanting this for a while, haven't you?" he asked.
"Mm-hmm," I mumbled, as I didn't want to let go of his yummy cock. I was aching for my hole to be fucked by this thick stick.
Before I could ask him to fuck me, we heard another person walking towards us. It was an older white man. He caught us off guard. Apparently he liked what he saw, as he already had his dick in his hand and whacking off to our little sideshow.
"Howdy, fellas! You guys, don't mind me. I'm just enjoying the show," the fella said. He got a look at my ass and said to my new friend, "Man, you sure are a lucky bastard to pull her out of the crowd, huh?"
"She's one-of-a-kind," he replied.
"Just look at how she sucks that thing," said the fella. "Man, I wish my wife sucked me off as good as your lady friend here."
"Hey, uh," my friend uttered before he let out a loud moan and fucked my throat a few times. I nearly gagged. I'm not a deep throat kind of girl. I gag too easily.
"Oh, my gosh. I was about to puke all over you. Don't do that! I don't deep throat. I don't have good gag reflexes!"
"Oh, sorry, baby. Uh, what's your name, again?" he asked.
"Again?" I thought. He didn't even ask me the first time. I nearly laughed.
"Sasha? You forgot, sillyhead?" I said. I had to go with the flow. The fella looked at us like we never met before, which is true. We just met half an hour ago. I looked at the fella and said: "We just started dating. Can't believe he would forget my name after, how many dates?"
The fella laughed. "Haha, I gotcha. Man, the way you're pleasing the man, you'd put any guy in a trance. Isn't that right, buddy?"
"Oh, yeah. You're darn tootin'!" my friend replied, as they laughed, and I continued sucking my friend's cock. It was not long until I heard them introduce themselves and I found out both of their names.
"Darius", my friend said. "Don", the fella replied. Good. Now, I can call them by their actual names.
"Hey, Sasha, why don't you hold off on my cock and help our buddy Don out?"
Don, the fella, was already on his knees and grabbing my ass. He had quite a gentle touch. I raised my ass so he could grope on me a little more.
"Wow, Sasha, you have a nice soft round caboose," he said, admiring it. He kneeled down further and started to kiss all over my ass cheeks. It really made my cock precum at the touch of his lips on my ass. Too bad I can't hit that tonight. My wife will kill me."
I stopped sucking Darius and turned over to Don. "It's okay,” I told him. “At least if I suck you off, she won't know anything. Pussy and ass juices will give it away, but a person's spit can't."
"O-okay, honey. If you're sure about th..."
Before he said another word, I lunged at his thick fat cock and started to suck him. His pre-cum didn’t taste bad. I was enjoying it. Don was getting shaky in his legs, so he said he wanted to lay down while I continued to suck him off. He thought he died and went to heaven when I started to flick my tongue under his cock. It seems to get every guy going when I lick there.
Darius kneeled behind me and kissed my ass cheeks passionately. He moved my thong to the side and pushed his hot tongue into my hole, which sent me to the edge. I loved it so much. The way Darius was tongue fucking my hole caused me to bob my head faster on Don. Darius wasn't done, though. He wanted to fuck me. I put my thong back in the middle and guided him to the hole I cut on the back. He liked what I did.
"Want me to put my dick through that hole in your panties?"
"Mm-hmm," I muffled. After he poked his cock through the hole in the thong, Darius slowly pushed himself inside me. It was hurting. I was feeling the burning of my hole as he continued pushing his fuckstick inside me. It hurt, but I loved how it hurt. I moaned so loud while Don's cock was still in my mouth. Don seemed to like what he saw.
"Wow, Sasha. You sure know how to please men, you little doll. It's too bad you're on your period."
Darius and I laughed. He thought that I was a real woman. I'd hate to disappoint him, though. I just went along with it.
"Yeah, but I don't mind getting it in my ass, too," I told Don.
"Yeah, a lot of you young girls seem to like that more these days, just like them homos. But, that's their lifestyle. Who am I to tell them how to enjoy sex?"
A bit relieved to hear that, I popped his dick out and said, "Exactly. Me, I love it both ways. But I always love when a man comes inside me, regardless." And I went back to sucking Don's dick faster. Darius' poundings got harder and Don was about to reach his peak. Because as he heard me say those words, he cried out, "Oh, honey, what I would do to fill up that pussy of yours. Oh, shit, I'm gonna explode!"
His dick got thicker inside my mouth as my sucking got faster on him. He started to buck his hips on me, grabbed my head, and started shooting gobs of his hot load into my mouth. Don let out a loud cry. His cream tasted so good. Darius couldn't believe his luck.
"Damn, Sasha. You made Don's day, let me tell you."
After Don emptied his load into my mouth, he slumped back on the ground, exhausted and shattered by how good it felt to get another chick help him get off. He rubbed his hand on my face and assured me that I didn't need to swallow if I didn't want to. That's good because I never swallow. He said his wife never swallows, but she's okay if he wants to come in her mouth. So, I spit it out.
We all needed a breather, so, Darius pulled out for a bit, and we got back up and adjusted ourselves. Don thanked me and kissed me on the lips. "You're gonna make a mighty fine wife, the way you pleased us. Just one rule of thumb. When you get married to that lucky man; no offense to you, Darius. Suppose it's you or another man..."
"No need to clarify, Don. It's cool."
"Well, as I was saying, when you find him, stay faithful. Don't do what I did. Or Darius."
I laughed. I told him it's okay. I wasn't looking to get married anytime soon. Not to another man, anyway, I thought to myself.
Then Don patted my butt like a gentleman and kept walking until he disappeared into the fog. It was nearing 1:00 am. Darius and I looked at each other. He moved his hand inside my pants and groped my hot ass again.
"You know, I'm getting hot in these pants. I'm just gonna take them off." As I peeled them off slowly, giving him another full show of my ass, he got all excited again.
"Are you sure you'll be okay without them on? It's gonna get cold again." Darius said.
"Don't worry. I'm still hot from our little fuck session that you haven't finished yet!" I said this as I bumped my ass on his cock.
He grabbed me and whispered: "Baby, you're gonna get it. Hard! Grind that ass on me, bitch!"
As I was grinding on him, I told him about this special place where people go to fuck, so I guided him there. It was about a mile up, but I told him no one would hear how crazy we would get once we were inside.
It's an abandoned fallout shelter left from the fifties or something that later turned into a haven for druggies, nymphomaniacs and all kinds of stuff. It was still fully functional with electricity, light and a door to lock ourselves in and do whatever we want.
As we got inside, checking to see if all was clear, kicked all the pipes and condoms from inside and away from the entrance, we finally lock the door and settled down on one of the wooden bunkers, turned the light on and just got back to making out. Darius stopped and asked me if it was ok to record us having sex. I said ok, and he gave me a copy of it when he came to my place later on in the week. I used my phone to record our wild moment as well.
After all was settled, we got back to making out, then I pulled his pants down and resumed sucking his thick cock. My ass was facing the camera. I bobbed my head faster up and down, getting him harder. He pulled my thong up my asshole. I begged him to pull harder. He did, and I moaned so loud. In this shelter, we can scream our lungs out. I was going to make sure to him that I will love every moment of his thrusting inside me. His cock got so thick. He pushed me hard onto the floor.
"Get on your knees, slut! Face on the ground, ass up! I'm gonna fuck you good!"
"Fuck me, baby. I'm all yours! Make me your bad bitch!" I screamed at him. I needed his cock. I was desperate. He found the hole in my thong, pushed through it and thrusts himself into me. Oh, the pain I felt when he impaled me so hard with his cock. I screamed bloody murder. I wanted more of it. Our camera phones were facing to our sides as he started pounding his dick harder into me.
I felt so hot. I pushed back on his cock. I begged him to fuck me more. The feeling was so euphoric. I was screaming words only the Almighty would know I said. Darius looked funny to me. His voice seemed to calm me, though. I let out a few deep “ooh” moans. I was loving every moment of his dick inside me. Darius loved watching me get so aroused.
"Damn, Sasha. You really this freaky with all the guys who fuck you?" He asked.
"Oh, fuck yeah. You have no fucking clue. I'm that bitch every man wish they had."
"You ain't kidding. I'd rather fuck you over my wife any day of the week. You got an ass a girl would kill for!"
Just hearing him say those words made me fuck his cock back. He pulled out and made me get up. He forcefully pinned me against the wall with my ass jutting out like the desperate and submissive slut that I was. He positioned our camera phones on the floor at the right angle, looking up at us from the side. Darius returned and thrust his enormous cock into me real hard, leaving me gasping for breath from the intensity of his fucking.
"You like it when I take control?" He asked.
"Oh, yes, Darius, baby. I love how you control me. I love how you control my tushy. You like to fuck your bae's big round tush?"
"Only when she's being really bad."
Then, he slapped my ass hard so many times while he fucked the shit out of me.
"Serves you right, bitch. Getting wild and hot on me like that!"
He then thrusts his cock real hard, leaned over and said, "You're bad. Really bad!" I pushed my arms against the wall so that I could push myself on his ass. He grabbed my arms and pinned them high up on the wall and thrusts his cock three more times. He leaned over again and whispered: "Now you're my slave bitch! I'm taking control!"
"Yes, please be my master! Aaahh!" I yelled as he went on thrusting his cock violently so many times. I was in a natural haze. All I remembered was that I was screaming and moaning so fucking loud, begging him to come. He wasn't finished yet. I didn't care how long it took, I needed his seed. Then we moved onto the ground, facing the camera, and cried out for him to come inside me. I needed his seed in me. He quickened his pace. He grabbed my hips so hard. He was about to come.
"Bitch, that's what you get for getting in my way earlier. Don't do that again, okay bitch? Now you're gonna take what's coming to you. Ready?"
I just screamed out: "Come inside me, baby! Fill your bitch's pussy up now!"
He screamed: "Here I come, bitch!"
He was at maximum speed, pounding my worn out ass, then locked into position, howled as loud as he did and grunted hard as he filled my ass up with his creamy hot load. It felt like an eternity, the amount of cum that was shooting into me.
"Oooo! Mmm, your cum is so hot and good inside me, baby!" I moaned out while I pushed my ass onto him back and forth slowly. I started to feel faint, probably from all that work and passion. It felt strange. Then, I got dizzy and suddenly passed out. I didn't know what happened after that night. I remembered waking up an hour later in the shelter with a text sent by Darius.
He got my number by calling out from my phone to his. My ass still ached so badly because of how hard he fucked me. I read from his text that he kept my panties. Dammit. Well, lucky for me, I had an extra thong, a red one. So I put them on, and just walked out without my pants. I didn't want to put them on anyway. So, I walked back down the foggy trail, just in my sweater, thong, shoes, and my pants wrapped around my waist so at least my ass was covered up.
I looked at my phone. It was nearly three in the morning! I thought about stretching a bit to shake off the pain and go jog about halfway down the foggy trail before I go back home. So I did. As I headed home, I noticed another man heading towards me. He looked about middle-aged, and whitish. He said he saw me getting fucked by this black guy while I sucked on another dude.
 He waited for me to see if he could get some as he showed me his cock. I just couldn't resist. Licking my lips to his thick cock, I said to him: “Oh, why not? All I ask is for you to be easy on me.” I also told him that I didn't care for his name or number as he tried to offer it to me. I just told him matter-of-factly: "Look, if you're just looking to get off, I'll be glad to help you out. It's what I love to do. But, that's it.".
He was okay with it. Before I could go down on him, I collapsed. "Are you okay?", the guy asked.
"Honestly, no. I partied too hard. Sorry that I can't help you tonight, sweetie", I said, feeling tired and beaten up.
He wasn't going to let me struggle. He pulled me up, grabbed me by the waist and helped me walk along. I told him I live about twelve houses down from where we were standing.
"I'm Billy, by the way."
"Sasha," I replied back.
"Sasha? That's a sexy name."
"Thanks. I like the name Billy, too."
He asked me why, and I just simply told him I was a fan of Billy Bob Thornton. Although this Billy looked nowhere near him, he was still very handsome. He looked to be in his forties, average build, five-feet-ten in height, and he had long and wavy salt and pepper hair tied up in a ponytail. He started us off. As he got comfortable talking to me, he moved his hand down to my ass.
"You got a nice ass for a crossdresser," he whispered. I just smiled back at him.
As we arrived, I thanked him, gave him a hug and told him he could meet me later tonight and I would take him to the shelter. Tonight, I could suck him off before he leaves. He didn't budge. He insisted on staying to help me. Curious.
"Well, yeah, I wanted you to blow me, and then fuck your brains out, but I felt bad seeing you in this state. The least I could do is comfort you for the rest of the night. If you don't want to get fucked and don't want to suck, I completely understand. But, at least, let me take care of you just for tonight."
His wide hazel eyes darting at mine, and the way he was softly stroking my butt was enough for me to believe how serious he was. I almost fell in love with him after he said that. I had to be real with him, though.
"Look, Billy, I'm flattered and grateful for your generosity, but, before we go any further..."
"You're seeing someone. That's totally cool"
"Well, yeah, I am. In fact, it's a woman."
"Hey, I totally get it. I'm bi, myself. But, I've always had a thing for crossdressers and transvestites, and I hope to date one soon."
How cute. I told him that I wish him the best. Still, he wanted to make good on his word. So, I hesitantly allowed him to stay the night. He made himself comfortable while I did the same by putting on a black satin thong babydoll nightie. His pupils widened at the sight on me.
“Damn, Sasha. You look so foxy in that babydoll,” he said. I modeled it for him, letting him see how it looked all around me, even teasingly jutting my ass in front of him. I was awarded with a hard slap on my ass. “Ow!” I yelled, giggling at him.
“Then you shouldn’t tease me like that, doll,” he said. “Look! You really woke up little Billy.” He pointed at his cock, which grew enormously inside his tight little red boxer briefs. I just winked back at him and jutted my ass again to tease him more.
“Oh, so it’s like that, huh?” he shouted. And before he tried to slap my ass again, I darted to the kitchen to get the wine. I conceded to the fact that I liked Billy and would let him fuck me, even if I was battered from Darius’ magical and maniacal fuck. I wanted Billy to fuck me, so I wanted to get us drunk.
“Vino?” I offered.
“Don’t mind if I do, babe.”
I went back to him and set the wine glasses next to the little table in the middle of the room. I purposely teased him by jutting my ass out to him while I bent over and poured the wine. He had fun fondling my ass that whole time.
The whole time, we were drinking wine while we talked about life, and what got me to like dressing up like a girl. He was petting me and cuddling me, rubbing my ass cheeks softly, sometimes giving me gentle wedgies. Billy said how much he loves seeing a thong disappear in a girl's ass. He loved how it looked on me. After maybe two bottles, he started to feel randy.
Billy lowered his face towards my ass and kissed it. He pulled his boxer briefs down and let me suck on his cock. It looked about eight-and-a-half inches and it was very thick. It was a good size. He was clean shaven all around his cock and balls. As his cock entered my mouth, he smiled so wide. It was a smile that moved me in some weird way. I went on sucking him slowly. "Sasha, you're so beautiful", he whispered to me while he rubbed the back of his hand on my cheek.
I just gave him a wink and went on enjoying the taste of his dick in my mouth.
I was okay to get fucked now, but we needed to be slow and quiet since I was back home. I moved the table away to make room for us and I put several pillows on the floor to position myself. The bed was off limits because it squeaks and I didn't want to wake up the landlords. Billy came behind me, found my hole on the back of the thong, put some lube in my hole and slowly pushed himself into me.
It was hurting a bit, so I asked him to be gentle. He agreed. Then after a few minutes, the pain subsided, and he pushed himself deeper into me. I was now enjoying this awkwardly romantic moment with Billy. The way he was pumping in and out of me felt like the way I moved when I made love to my girlfriend. My heart was beating so fast. My moans got deep and soft. I called out Billy's name so many times. It was a natural high. His sawing into my hot ass back and forth felt so sublime, and the noise of his ball sack slapping against my ass was like hearing music playing.
"Wow, Billy. Is this how you fuck every transvestite or girl you date?"
"More or less," he replied. "Why? Is it taking an effect on you?"
"Ugh, yes, it is, baby. Oh, I love how you're doing me. You put so much passion into it."
"Yeah, when I fuck, I make sure I put some love into it. I want her, or you, in this case, to feel my vibe every time I thrust in and out of you. I want you to feel the passion. I want you to feel the love."
I forgot that I was at home and I was supposed to keep quiet, but I was lost in the moment. I moaned so loud and pushed my ass really hard onto him so I could feel all of his cock in me. I wanted him deeper in me. Just the words he was saying, the way he was talking, I couldn't help what had followed.
"Oh, shit. No guy has ever made me feel like this. Oh, my God!"
“Feel like what, Sasha?” he asked, picking up a little speed in his deep thrusts. I arched my ass higher, begging him to go deeper in me.
"Dammit, what you're doing t... holy fuck! I'm gonna... ooooh!"
Before I could finish talking, I came all over myself. I was paralyzed by the way he talked and fucked me. He watched my reaction as my eyes rolled to the back of my head. My body convulsed. It was a feeling I never imagined would ever happen to me. Just after I climaxed, Billy quickened his thrusts.
"Sasha, you're so beautiful. I never thought my love-making would cause you to feel this good. You're such a beautiful creature. Are you ready to feel my love take over you?"
His thrusts got harder and deeper, and he felt so hot inside me. I was ready. Ready than I ever was.
"Yes, Billy. Fuck me harder. Give me your love. Give it all to me! Cum inside me! Please cum inside me!"
I pushed my ass faster on his cock. He grabbed my hips kept my ass arched really high. He stopped as he moaned softly and shot gobs and gobs of his really hot loving semen inside my love hole. I felt all of it. Every single shot he made. I was in heaven. This was beyond anything I had ever felt.
After a few minutes, he pulled out and got cleaned off. I still laid there with my ass in the air, totally mesmerized by what just took place. Honestly, I didn't want it to end. As I got up, I felt his semen run down my ass. I looked at how messy my thong looked after I came so hard in it, all thanks to this lovely man. I got cleaned up and changed. I wore another blue thong babydoll nightie. It was almost 5:00 am. Man, where did all that time fly?
"So, how did you like our little love session?" He asked while he patted my ass.
"Oh, shut up. You... you... ugh!" I said, exasperated.
"It's cool, babe. You never experienced the art of making love from a woman's perspective, until tonight."
Well, that's one thing I have to admit. It was an awesome feeling.
As I got into bed, Billy followed. As he spooned me, I felt his cock getting rock hard again. I responded to his erection by pushing my ass back on him.
"Billy?"
"Yeah, Sasha?"
I got pretty emotional, but I managed to hold my tears.
"Thank you... for making love to me.” I paused for a moment, swallowing my heart-filled tears. “No one has ever done that before."
"No worries, babe," he whispered. Then, he kissed my shoulder.
He made slow love to me one more time, emptying his love deep into me until he fell asleep. I loved how this night ended.
It wouldn't be the last time I met with Billy. Some secret dates and passionate love-making sessions later, he gave me the most wonderful present that only a girl could ever dream of. Of course, it didn’t come without its problems and dilemmas. A huge dilemma, in particular: making a choice between him and my girlfriend.
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