This is Chapter two in a series. Make sure you read the first part first!
After the disaster with Matt I was torn as to who to date next. I still wanted a real man inside me in spite of how good as Tina was with the dildo. On the other hand, I was kind of over my passive stage and wanted to fuck some ass. I didn’t care who it belonged to…
The week flew by and I figured I’d go to 'Eric's', one of my favorite clubs Saturday night and just pick up whoever I could. At this point I just didn’t care. I was horny, my hormones were raging and couldn’t wait to unleash it all on some unsuspecting dude or dudette.
Saturday evening finally arrived! I got to the club early and got a seat with a great view of the dance floor. I watched a really cute gay couple dance together, with other guys and with a few ladies too. Over the course of the evening they got racier and racier until one of them crossed some boundary. It looked like the cute one let some girl put her hand down his pants but apparently that was supposed to be off limits. His partner called him a bunch of names and stormed out. He stood there in the middle of the floor with everyone staring at him. I caught his eye and motioned him to come over. He was maybe 5’9”, slightly built and had incredibly delicate features for a guy. I was instantly attracted to him. And I’d have killed him for his shoes. The only problem with dressing as both men and women is that I have to cut my wardrobe money in half. This guy knew how to dress! His two-day stubble was super sexy and his hair was neatly messed up just SO.
“I’ve been watching you two all night. Damn man, you sure have the moves,” I said with a smile. “I’m Chris by the way.”
“Hi Chris,” he said with an amazingly deep voice. “I’m Jake.”
Tonight I was dressed in a guy’s black suit coat, guy’s dress shirt and black slacks. With the hat tilted down over one eye I thought I was looking pretty hot.
“So what’s with you? You here alone or with your girlfriend?”
I figured I go with his plan and said “Yeah, she acted kinda like your boyfriend. Felt threatened by all the hot pussy in this club.” I winked at him.
“Hey, they terrify the hell out of me too,” he said with a laugh. "Not sure what I’d ever do with one of those. But I’ve always been curious.”
“You should try one! They’re great fun!”
He laughed and looked at me like I was crazy, but I let it go. We chatted for a while and he was totally charming. I realized that he still thought I was a guy, so I decided not to disappoint him. I was running my hand up and down his thigh and finally grabbed his cock while looking into his eyes. I could see my lust echoed back to me through his steel grey orbs. Time to make my move!
Upstairs at Eric's
“Meet me upstairs in that dark corner with the booth in 5 min. I have to pee.” And with that I got up and left him there with his mouth open. Sure enough, in 5 minutes he came wandering back to me. I kissed him deeply and ran my hand down into his pants.
"Oh man that feels so fucking good Chris," he whispered breathily in my ear.
“Do you want me? Do you want me to fuck you? Right here?”
“Oh my God, yes,” he nodded enthusiastically. “Fuck my ass right here!”
“We can’t right here. But follow me.” I got up and turned left down the hall, opening the first door on the left. It was a small meeting room, but one wall had windows that opened up onto the dance floor below. I pulled a small table over in front of the window and pushed him down on his stomach across it. I walked around to the other side in front of his face. I yanked down my pants and pulled my cock out through my fly.
“Suck it. Make it all hard and slippery for your ass.” I grabbed his hair and shoved my cock into his mouth. My width made it hard for him to take more than half of me without gagging, so I just fed him what he could take. I wasn’t going to be so easy on the other end. He slobbered all over my length, getting it dripping wet. I was dripping wet too! Walking around behind him I ducked my fingers into my panties and smeared my cock with my own pussy juices before laying my tip against his rosebud. My tip is pretty small, but it flares out quickly into a huge width just behind the head so getting the tip in is pretty easy. Then it is just a matter of giving the recipient time to get accustomed to the increasing width as it slides in. Lubrication is the key! I pushed the tip in and Jake moaned deeply. He pushed back towards me, impaling himself a little bit at a time. He looked back and his eyes got wide as my full width stretched his ass to the limit. As the widest part slid past, he groaned long and low.
“Fuuuuuck, that feels so good! Pound my ass. Come on, give me that fat cock!”
I built up a rhythm and soon was giving him all I was worth. The table was rocking alarmingly on the floor and for a moment thought the whole thing was going to topple over. Finally I could feel my release building and then went over the edge in a rush, emptying myself into his bowels. I lay on top of him as we wound down and suddenly I had a plan…
Just then we heard some drunken couples coming up the stairs so we quickly got dressed and hurried back downstairs. The couples looked at us and I could tell they knew what we had been doing but at that point I didn’t care. I dragged Jake outside for a break and we sat on a bench and drank some cold beers I’d grabbed from the bar.
“Thanks for that,” I said truthfully. “But I owe you one! How about you come back to my place and I let you return the favor?”
“I don’t know,” he stammered.
“Oh come on. I’ll let you in on a little secret and you can have my way with me. I mean, have YOUR way with me. Wait, those are the same things,” I said slurring my words slightly. The lust returned to his face. Nothing like a drunk horny date to get your libido up! I grabbed his hand and started walking down the sidewalk towards my place.
“Your boyfriend is a dick. I saw the whole thing and I don’t think you did anything bad at all. You’re a great dancer and you have a fascination with women’s bodies. WTF is wrong with that?
“Ok, so you’re right. I mean I love being gay. I do. But I’ve always wondered…” and his voice trails off to nothing.
“What?” I ask. “You wonder what they look like? Feel like? Taste like?”
“Well I’ve seen plenty in magazines and porn. But yeah, I’ve always wondered what it feels like to sink my dick into one.”
“It feels fucking great! A pussy is so much softer than an asshole. There’s not nearly as much muscle and the sensation includes sliding along the walls. A butt doesn’t feel like that at all. Once you’re inside, there’s nothing, you know?” I could tell he was thinking hard about it.
Home Turf
We walked into my apartment and I opened a bottle of wine. Soon we were sitting on the couch and laughing like we were sorority girlfriends. Eventually I steered the conversation back to the club.
“I think if I remember correctly that I owe you my ass. Seeing as I fucked yours at the club. You ready to collect, Jake?”
“Oh yeah, I’m ready,” he growled.
I stripped my pants off and leaned down on all fours, wiggling my ass at him.
“Damn, you have a really narrow waist! Or really wide hips,” he said quizzically.
I lowered my boxer shorts until just my tight hole was exposed, and grabbed a bottle of lube and squirted some on my ass.
“Do you wish I was a girl? Just to play with?” I say over my shoulder.
“Oh, that would be so hot!” he said as he knelt between my calves.
“Jake? Remember that secret I said I was going to share with you?”
“Yeah,” he said hesitantly.
“Look right at my asshole.”
“Okay…”
I slowly pulled down my boxers, exposing my dripping snatch.
“What the fuck?” he said quietly. But he wasn’t freaked. He was mesmerized.
“But, you fucked me. I sucked your cock. How is this possible?”
“I’m really a girl. But I was born with a penis too. I can come either way. And now you
have a choice. You can fuck my ass. Or you can fuck my pussy. But I’d love it if you do both!”
I think Jake thought he’d hit the lottery. “Can I touch you?" He asked enthusiastically.
"Can I finger you?”
“Yes, please finger my pussy. And my ass,” I beg.
He slowly rubbed a finger around my tight sphincter, sending shivers through me. He probed deeper until his finger slid inside. Soon he had two fingers in my ass and the sensations drove me wild.
“Can I do this to your… your…”
“For God’s sake Jake. Say it. Say ‘Pussy.’”
“Okay. Can I finger your pussy?”
“Yes, but use your other hand.”
“Oh,” he said, thinking I didn't want his ass-fingers in my pussy. He started to pull them out.
“No, no! I mean – leave your fingers in my ass and use your other hand. That way you can really feel the difference."
The fingers of his other hand slid up and down my wetness as he slowly explored my lips. I could tell they were like nothing he’d ever felt before. And I was happy to let him explore me that way. His grin told me he was enjoying himself so I just let him take some time. Finally he started working his fingers around the entrance to my pussy and when he slid his two middle fingers inside I thought I was going to come right then and there. God, it felt so good! I don’t exactly know what he was doing but he hit every button, spot and zone in my body. I shrieked that I was going to come and I exploded, clamping down on both sets of fingers as my body’s spasms wracked my pussy and ass.
He kept gently fiddling with me as I wound down sending delicious aftershocks through me.
“Whew, that was fucking FABULOUS,” I said dreamily. "But I really want your cock inside me. Why don’t you try my pussy first and then you can finish in my ass if you want?”
Jake loses his virginity - again
“Uh, ok.” It isn’t going to hurt you or anything will it?” he said sheepishly.
“Oh heck no, I love it in all my holes!” And with that he lined his stiffening cock up against me and for the first time in his life entered a woman. I felt his entire cock slide inside me. I was so touched I almost teared up.
"Jesus," I thought as he slowly stroked in and out. Had he GROWN since the club? I was completely filled and his delicious balls were dangling against my ass. I couldn’t wait to feel them slapping against me.
“Oh wow, that’s NICE,” he groaned. "Damn, you’re so slippery! Is it always like this?”
“Well, yes and no,” I said. “If I’m not turned on then you’d have to use lube just like on my butt. But if I’m into it I’m always a soaker. Though not all women are this wet.”
He stroked in and out of my aching folds for a while, reveling in the new sensation. Then he pulled out and laid his rock hard tool across my wrinkled sphincter. I panted with anticipation. Slowly rubbing his tip against me made me crazy with desire and my hole relaxed enough that he was almost pushing his tip inside me with each pass. Finally the head slipped in, and I groaned with that unique feeling of something full and alive in my bowels. I love sex in my pussy. I really do. But there is something so intimate about anal sex that nothing really compares. It is dirty, naughty, intimate, private all rolled into one.
God, I love it! Jake added a little more pressure and soon he was balls deep in me. I reached into my night stand and took out one of my favorite toys – a nice thick 8” cock that was quite lifelike in heft and feel. I worked the tip between my lips and with a groan slowly shoved its full length into my sopping pussy. Jake could feel it as he plunged in and out of my ass. With a shoulder on the floor I could thrust my toy into my pussy with one hand and stroke my ready-to-explode cock with the other.
“Fuck that feels fantastic,” I cried.
“Yeah, but I have an idea,” Jake said with an evil grin. With that he pulled out of my ass, yanked the dildo out of my hand and went to the bathroom to clean them off. Returning, he lay between my thighs and just gazed at me.
“I’ve just never imagined anything like this,” he said quietly. “I mean, you’re perfect. You have anything a guy or gal could want! Why are you single? I’d think you could have anyone, anytime.”
“Ha!” I laughed. “You’re gay. You know how incredibly close-minded people are. How rude, and judgmental and just fucking MENTAL people are! I am fucked over by EVERYBODY. Guys can’t handle that I’m better hung than they are, and they have the whole homo-phobic thing going on which you understand. Women just don’t know how to deal with me. Some days I’m feeling masculine. Other days I cry for no fucking reason and then want to kick the shit out of someone over nothing. I really don’t fit in anywhere. I’m lonelier than you can imagine…”
“That is so sad,” Jake said with real feeling. It was the nicest thing anyone had said to me in a long, long time.
“Let’s see if we can improve your mood!” With that he worked the dildo up and down my sloppy folds. He scooted up close and ran the tip against my sphincter. Within a few minutes he had about half of it in my happy ass. Suddenly he got up on his knees and speared my pussy with his shaft. When he got a bit more than the tip in his pubic bone hit the back of the dildo, which had a lifelike pair of balls hanging down. As he leaned into me, his cock slid deeper into my pussy and the dildo was pushed further into my ass. Holy shit, was I full! Long determined strokes worked the rest of the rubber cock into my ass. Every thrust pounded against the base sending shivers of delight deep into my bowels. He grabbed my hips and really started letting me have it with long savage thrusts. His balls were slapping against my clit and I could feel a humongous orgasm approaching. His breath was getting ragged from all the exertion so I didn’t mind him leaning forward until he was lying on top of me. What I didn’t expect was his hand snaking underneath us to grab my cock! He’d lubed it up without me noticing and when his grip tightened around me and started pumping I totally lost all control.
I screamed, bucked against him and thrust my cock through his tight fist. When the orgasm hit me I came so hard, so violently I thought I tore something inside of me. Jake bellowed and blew a huge load in my ass. I couldn’t breathe, couldn’t see and passed out on the floor, Jake and the dildo still deep inside me.
“Oh my God!” Jake screamed. “Chris! Chris! Are you ok?”
I slowly came to with my head in his lap. He’d rolled me over and was cradling my head in his hands. “Jesus H Christ you scared the shit out of me!”
“Yeah? Well you literally fucked the shit out of me! I’ve never come that hard before in my life! How the hell did you do that?”
“I guess we’re just really compatible, huh?”
“Yeah, you could say that.” I lifted my head and kissed him even though I was upside down. “I’m really wiped. Why don’t we take a breather and relax in my bed?” I got up and shakily wobbled back to my room, Jake in tow. I was asleep before my head hit the pillow.
Morning wood
I woke up the next morning on my side, with Jake curled up behind me. I slowly ground my hips against him making him groan in his sleep. His morning wood had a mind of its own and happily slid between my thighs. I rocked my hips back and forth spreading my wetness along his length. I tilted my pelvis backward and centered him against my pussy and slid him deep inside. His mind was asleep but his body knew what to do. He started humping into me gently and I responded to each thrust with a twirl of my hips. Suddenly he woke fully. It took him a moment to figure out what was happening. I couple thrusts of my hips left him no doubt what I wanted. He started fucking me in earnest and in no time I could feel him getting close. I banged back against him driving every inch into my body. His last lunge was just an inch too far back. His cock slipped out and slid along my lips. His come shot out of him and landed all over the sheets, my thighs, our pillows and in my hair. We both laughed as I tried to wipe up the mess with some tissues.
“Shit, dude, did you have to blow half a gallon of cum all over everything?”
“It wasn’t my fault! You started it!”
I grabbed his face and kissed him lightly. “Let’s get cleaned up and then come back to bed. I still haven’t gotten mine yet.”
Jake looked at me like I was kidding. When he realized I wasn’t a huge grin spread across his face.
“You know what Chris? I like you. I like you a lot! I think I’m going to die a horrible dehydrated death but I’m willing to risk it!"
The shower went about as expected. Neither one of us could stay terribly clean for long. We weren’t in there 30 seconds before Jake soaped up his hands and then ran them all over my breasts. My nipples are super sensitive and in no time I was rock hard and panting heavily. I spun him around and soaped up his chest, then worked on his shoulders letting plenty of soap run down between us. After rinsing that off, I took a handful of conditioner and rubbed it all over his ass and balls. He groaned and leaned forward more, pushing his ass back against me.
I rubbed some conditioner on my cock and ran my tip up and down his crack. He was totally turned on and my tip sank willingly into his tight butt.
“Fucking hell, that feels good,” I moaned in his ear.
“Yeah it does. Come on sweetie, give it to me like you mean it.” With that he thrust back bottoming me out inside him.
I grabbed his hips and pounded him in earnest quickly building my need until I couldn’t hold back any more. I dumped my load deep in his ass and then smacked it hard.
“Ouch! That stung,” he said rubbing his cheek. “Let’s see how you like it!”
Jake spun me around and kicked my feet apart, spreading them wide. “Grab your ankles, biatch!” With his raging hard-on in his hand, he guided himself between my folds. In one thrust he buried himself in my pussy and without a millisecond pause started pounding me furiously. My vision blurred from the power of his onslaught. I don’t know if I have a prostrate or not or whether he was hitting my g-spot. All I know is that I felt an unusual heat in my belly and my cock rose magically from the dead just minutes after a huge orgasm in Jake’s ass. But there is was, rising slowly until it was pointing up my belly and waving around with each thrust from Jake. I took myself in my slippery hand and started yanking my meat in time to the pounding I was taking. With my legs spread and only one hand on the floor I was pretty wobbly. Jake grabbed my hips hard and kept up his onslaught. I could hear the change in his breathing and I knew he was going to blow.
I increased the speed of my hand hoping to catch up. Just as I went over the edge so did Jake. He pumped one last time and spewed inside me.
Damn, could that guy dump a load! I could feel it running out of my pussy and down my thighs. I squirted my load in long roapy strings all over the floor. The water streaming down on us slowly washed big clumps down the drain while we tried to regain our breath.
“Ok”, he wheezed while helping me stand up again. With all that blood rushing to my head while I was bent over, the room was spinning pretty hard. “That was AMAZING! I love being gay, but damn, pussy is fabulous!” I laughed at him and shook my head as I turned off the water and retrieved a couple towels.
“Yes they are. I love having one and being able to fuck them too!”
“Alright girl. I’ve got to run but can we do this again? Soon?” He looked at me like he was afraid this was going to be a one-time deal.
“Oh hell yes,” I replied eagerly. What are you doing this weekend?”
"Nothing really," he said slowly. "What were you thinking?"
I smiled wickedly. It’s good he couldn’t read my mind…
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Other stories by J. J. Krause
10 Minutes - An erotic anthology of 9 short stories. What would you do with 10 minutes?
Road to Darlon - Set in the distant future, two friends search the Galaxy for the Mulae, the best sex in the entire galaxy. But one friend has a secret that could get them both killed... How far would you go to find the best sex ever?
Check back often for the release of 'Triple Play'! Adam, auto garage owner and part-time racing driver meets two lovely ladies. Can he choose just one?
About the Author
J.J. grew up in Northern Indiana, but has lived all over the US, including accidentally spending a year in Las Vegas. (Long story. Maybe another book?) He also spent 6 months in Belize, Central America working with elementary school students. For over 25 years he has taught high performance driving for BMW, Porsche, Ferrari and other exotic and sports car and motorcycle groups. He can normally be found in the left lane, traveling "Mach Schnell." Watch your mirrors, and give a friendly wave...
I write under jjkrause so be sure to search for all my stories!