For context: My fictional self has befriended Jen, a small framed scientist that was introduced in the very first chapter of the series. After a series of mini dates together, the two end up in Mike's bungalo bathroom. Both Mike and Jen are lightly intoxicated from scotch and tropical mixed drinks, respectfully.

I started filling the bath. Jen understood my plan and sat up. I helped her out of her red dress, exposing her little breasts and protruding nipples. My earlier theory of her forgoing a bra proved true. With the girl fully naked, I took my time as I removed her hair tie carefully. The girl's blonde hair fell to her pale shoulders, wavy and beautiful.

“Thank you for taking me out,” Jen said with a blush.

“You're welcome. Did you enjoy our evening on the water?"

We were both salty and a bit grimy after a sunset cruise in the red daysailer.

"Yes. It wasn't what I expected to do when I asked to go out on the boat. But I enjoyed it a lot.” Jen conceded.

We locked eyes for a moment. Without any further discussion, Jen pulled meinto an embrace and kissed me deeply. My eyes were wide open for thisaction. I was fuzzy from my scotch, but I suspected that Jen was quite drunk from her Pina coladas. And she was naked. And kissing me.With tongue.

“I think...we should both clean up,” I prompted.

I broke the embrace and pulled the plunger on the bath spigot. Water began spraying out of the shower nozzle onto the puddle of water in the tub. I checked the temperature of the water, adjusted the setting slightly and pulled the plug out of the bottom. Then I ushered Jen into the shower and closed the curtain. With the girl out of sight, I shed my clothes and took a quick look at myself in the mirror. I wasn't hard yet, but it probably wouldn't take long for that to change.

I carefully climbed into the shower. Jen was soaking wet already and pulled me into a embrace. We kissed, passionately, for some time. Her hands were all over my head, then worked their way down my back. Jen grabbed on to my ass playfully. I snickered and did the same for her petite posterior. We made out for some time as steam fogged the mirrors and filled the air in the bathroom.

Our naked, wet bodies clung close to each other. I grew hard and felt my cock poking the girl's pale belly button. Jen looked down atthe offending organ briefly and snickered.

“Somebody is happy to see me I think.”

“You think?"

We made out some more, then both bathed each other. Jen took care to scrub my intimates gently with lots of body soap. It amounted to a brief, but hot, handjob in the shower. I returned the favor, illiciting a feminine whine of pleasure as I rubbed the girl's clit. Soap and water sluice dacross her small breasts, down her flat stomach and across her shaven groin. Eventually, we had both run out of excuses to stay in the water and the shower was secured. I was reaching for my boxers when Jen stopped me gently.

“Let's just go lay down,” she prompted.

Yes! Finally!

We retreated to the bedroom. Jen crawled under the covers, completely naked. Meanwhile, I went into the living room and turned the TV off. I pounded the last of my scotch, got us both glasses of ice water, then returned to the bed. Jen had the covers pulled up to her chin.

She eyed my naked form with a smirk. The smile continued as I crawled under the covers and pulled her into an embrace. We made out for a bit more.Then my hand slowly made its way down to the girl's clean shaven groin. I touched on either thigh, then slowly ran a finger from the bottom of her little, wet, hole to the top. Jen wriggled beside me with eagerness. Then I slowly began working on the girl's clit. Jen, as I found, was quite easy to please. The girl climaxed in less than two minutes. Her orgasm sound was high pitched and breathy and hot as all Hell. I was as hard as could be.

Jen was soaking wet now. It was easy for me to take my index and middlef ingers and moisten them before easing my fingers inside her extremely tight vagina. Jen inhaled sharply as I penetrated her sex up to my knuckles. I surmised that it had been some time since she had had any internal stimulation. I used my second hand to play with the girl's clit as I slowly began finger fucking the girl's vagina. In short order, Jen came again. This time, I could feel her vaginal walls clenching down on myfingers, trying to suck them upward into her body.

“Oh, that was a good one,” Jen moaned happily.

“I can feel that.”

I stopped finger fucking, but left the digits deep within the girl.

"I want you,” I said flatly.

“I know you do. I want you too,” Jen conceded.

“Are you ready for what comes next?” I probed.

Jen nodded after sighing.

I withdrew my fingers, then started to crawl on top of the girl.

“Whoa whoa. Do you have protection?” Jen said.

I stopped, hovering halfway on and off the young woman's body.

“Uhh...hold on. I think I have some condoms in my sea bag.”

I jumped off the bed and began tearing through my closet. I retrieved astring of Trojan “for her pleasure” condoms and sprinted back to bed. I showed Jen the purple foil package triumphantly.

“Mike, that's not going to work...”

My heart dropped.

“What? Why? It's for your pleasure. There's no need to worry. I've got other kinds if you would prefer.”

Jen shook her head.

“Mike. I told you this, I thought. I'm allergic to latex.”

Shit. Every condom I had in my possession was latex. I knew that they made latex-free condoms but I'd never used or purchased one.

“I must have missed that...”

I felt like the rug had been ripped out from beneath me. But I was drunk and horny and I knew she was the same. I wasn't ready to give up on sex just yet.

“I'm guessing that you're not on birth control?” I asked.

“No. Every time I've tried one, it makes my cramps awful,” Jen explained.

Jen was hot. I liked her, a lot. But completely unprotected sex wasn't a risk I was willing to take with a girl I barely knew. Pregnancy was a scary prospect with a virtual stranger.

A bit crestfallen, I lay beside Jen and stared at the ceiling fan above us.Jen, sensing my defeat, snuggled up to me for a bit. Then she kissed me.Then I kissed her back.

The next thing I knew, Jen was on top of me and we were making out again.Jen ground her hips onto mine, forcing my boner to drag on her shaven landing strip. I was so close, yet so far. I grabbed onto Jen's legs, then ass. I had a handful of cheek in each hand as we made out. The room was a mix of darkness, warmth, wetness and arousal. I wanted Jen more than I'd wanted pretty much anybody.

Jen managed to sit up a bit, exposing my erection. With one hand braced on the bed, she teased my cock with her other hand. I nearly cried with the attention. Spurred on, I reached my fingers towards each other, grabbing more and more of her butt cheeks. My index finger brushed across Jen's little butthole and the girl arched her back slightly, relishing theattention. I continued playing with the puckered stretch of skin for a fewminutes as Jen ground her hips into mine. I pressed on the opening a bit, expecting to hear a complaint, but none were emitted. The girl took the posterior attention in stride.I pulled a hand away and sucked my index finger quickly. Then I placed the finger on Jen's rosebud again and slowly eased it inward.

Jen exhaled sharply but did not stop her kissing me or playing with my erect penis. Eventually, I had my whole index finger buried in the girl's extremely taught and warm ass. With no complaints filed, I began to finger fuck Jen's ass. The girl moaned and arched her back like a cat.

“You know, there is something we could do that doesn't require a condom...”I posed carefully.

“Yes. I'm aware,” Jen conceded, breathing deeply.

My gentle but deep fingering of the girl's rump continued. Jen abandoned her attempts to give me pleasure with her hand and used both hands to brace on either side of my body.

“Have you ever...you know...?” I probed as I probed.

“Well yes...but no...” Jen replied.

“You seem to be taking a finger pretty well,” I pointed out.

Jen nodded before groaning with, presumably, pleasure.

“Yes. But still...”

I slowed my digital penetration of the girl's rectum a bit.

“I would go slow and be super gentle. I'd stop if you wanted me to, at anytime,” I explained.

Jen arched her back a bit, grinding her front onto mine.

“You have lube, I assume?” Jen asked.

“Yes. KY. Great stuff. I'd use a lot of it and go super slow,” I answered and promised.

Jen clenched her ass around my finger a bit, considering my penis sliding into that tight spot.

“You promise to be gentle?” Jen posed.

“Of course hun.”

“Okay then.”

“Okay then?” I confirmed politely.

“Okay then,” Jen repeated.

I removed my finger from the girl's rump and rolled over to my bedside table. A bottle of KY jelly was retrieved and a healthy dose of the gelatinous liquid was distributed on my already moistened index finger and middle finger.

Jen rolled onto her side, presenting her backside to me and adjusted the covers. Back under the covers, I spooned up behind the girl and kissed hershoulders and neck. The latter contact made the young woman sigh a bit. I worked my left hand across her side and began teasing a nipple seductively.Jen mewed in appreciation as I gently twisted and pulled the sensitive bit. Next, I used my right hand to part the girl's cheeks slightly, then dabbed a bit of lube on the girl's button anus. Jen tensed up a bit.

“Relax. I'm not going to hurt you,” I promised softly.

My index finger was placed on the girl's butthole as I said this. After a moment of pause, Jen wiggled her backside. I took the hint and slowly pushed my finger into her deliciously warm and tight ass. The KY was much better than my saliva, I found. My digit invaded her hind quarters with ease. I gently withdrew the finger, then pushed back in a bit,then pulled it out entirely, spreading lubricant with each stroke.

“See, not so bad, right?” I posed.

“No. That lube works really well,” Jen admitted.

“Agreed. Told you it was good stuff.”

I placed both of my lubricated fingers on the girl's opening and applied abit of pressure. Initially, I felt Jen fight the intrusion, but then,suddenly, she opened up a bit. Both fingers slid into her back end. I gently spun the fingers around a bit, trying to spread more lube and open the girl up some more. All the while, I was still pulling on the girl's nipple gently. I removed my fingers slowly and heard a distinct pop as Jen's ass closed up.

I rolled away and used a baby wipe to clean my now slightly sticky and stinky fingers. Then I picked up the bottle of lube and squirted a dollop of the jelly onto my raging erection. I spread the substance across my girth, then squirted just a bit more onto my tip. I cleaned my hands off again and rolled back over, under the covers. I snuggled up to Jen, letting my erection find its way between the girl's taught ass cheeks. I reached around with one hand and began playing with the girl's clitoris. The other,however, was used to feel for the girl's anus and line my cock up forpenetration. The tip of my dick was placed directly on the girl's opening before I paused.

“Are you ready?”

“Just go slow,” Jen said with a nod.

I gently began to ease my girth upwards, pushing against a taught sphincter.

“Relax,” I chided gently, stopping my progress.

Jen breathed deeply, bracing herself. This action caused her ass to loosen slightly. My dick slid in a half inch. The girl panted for a moment, then relaxed herself again. Again, I slid in another half an inch or so. But then I was past her sphincter. It felt like I'd stuck a rubber cheerio around the tip of my dick. I repositioned, then pushed in a bit more. The resistance was a bit less now as I penetrated deeper and deeper. Finally, I could fit no more of myself in Jen's ass. Everything was was gloriouslywarm and amazingly tight. Once I was fully inside the girl, I stayed put,letting the young woman acclimate while gently rubbing the girl's clit.

"That's...that's a lot,” Jen said, clearly a bit overwhelmed.

“Are you okay?”

“Yes. I'm okay. It's just. It's just big. I feel so full right now.”

I don't care what any other man claims: When a woman states that you are well endowed, regardlessof the situation, you feel a sense of pride unlike any other. Nevermind that I'd finally, after a lot of waiting and sometimes awkward conversation managed to work my cock inside Jen. This too, made me feel pride. I'd reached a point that surely very few people had in the past. Or maybe this was the girl's first time engaging in this form of intercourse? Her answer had been somewhat vague.

“That feels really good, by the way,” Jen said.

“What this?” I asked, rubbing her clit a bit harder.

Jen whimpered happily.

“Or this?” I posed before moving out and in an inch or so.

Jen breathed deep. I took that as a warning to slow my roll in her backhole. I stopped any motion of my penis that would cause me to slide in orout.

I continued my attention on the girl's clit. After a minute or two of the rubbing, Jen began to move around a bit. I felt her ring muscle sliding up and down the base of my shaft a bit and it was absolutely epic. Jen started to breathe heavier and faster. I increased the pace of my clit rubbing.

Jen continued to writhe around, pushing her front into my hand. This caused my cock to slide out a bit. I answered this by pushing my way deeper with my cock while pushing harder with my hand.

“Nearly there,” Jen panted.

“Good,” I pulled out a bit then pushed back in gently.

“Nearly there,” Jen repeated.

I answered with a slightly longer stroke.

“Sooo close,” Jen relayed.

I could feel the girl clenching herself around my cock as she approached an orgasm. It was the hottest thing I could imagine at the time.

“Nearly there...” Jen said again.

“You can do it baby. You can do it,” I urged.

I was now rubbing the girl's clit with even more fervor than before.

“And! And! THERE!” Jen cried out as she orgasmed.

I felt the girl writhing all over, causing my dick to slide in and out ofher ass. I could feel her muscles tightening and loosening in spasms. The girl practically cried with pleasure. I pulled my hand away from her groin.

“Feel good?”

“Very. How, how about you?” Jen panted.

“You feel amazing,” I replied honestly.

“Good.”

Jen took a moment to collect herself, but then started to move her torso and ass in slow waves, causing me to slide in, then out of her asshole,then back in. It felt amazing. I reached down and started firmly but slowly working on Jen's clit again as we slowly side humped on the bed. This went on for a minute or so before my hand was brushed aside.

“I'll do this. I want you to focus on you,” Jen said.

Immediately, it became apparent that the girl was accustomed to pleasingherself and that she wanted more force with her clitoral stimulation. Jen climaxed again in short order. Again, she clenched onto my cock with her ass like a vice. I began slowly grinding and humping with a bit more forceafter the wave of the orgasm had ended.

“How's it feel?” Jen asked, resuming her clitoral rubbing after her brief pause.

“Amazing. You feel A-mazing”

“Good. I want you to finish. You deserve to cum,” Jen urged.

That sentence was hot as all Hell to my drunken mind. I increased thestroke and speed of my humping a bit. I could feel that Jen was now a bit more relaxed than before.

“Here, let's move a bit,” I prompted.

I pulled out of Jen's butt entirely, eleciting a moan from the girl. Using the opportunity, I quickly reapplied lube to my member. Then I guided Jento reposition herself on her back, facing me. I brought the girl's legs upto her chest, exposing her anus and sex. The girl got the hint and was rubbing her clit frantically as I slowly guided my girth back into her ass.I paused to let her acclimate for a bit, then resumed humping. I bent down and kissed Jen passionately, with tongue, for awhile. Then, I repositioned again and began sucking on a nipple.

"Getting close again,” Jen announced.

“Good. Me too,” I replied.

I could feel the tightening in my groin that indicated an upcoming explosion.

“Wait. Am I allowed to come in you?” I asked as I pumped a bit harder.

“Yes...yes...of course,” Jen replied, straining with effort from her rubbing and taking me.

“Good. It's coming really soon...oh real soon...”

Jen nodded and rubbed her clit ever harder. I switched nipples and sucked real hard. The girl let out a wail of pleasure. I felt her body tighten and moving all over beneath me. Jen yelled out as she climaxed and that was allI could take. I drove as deep as possible and unloaded into the girl's tight ass. Her ring muscle gripped and slid up and down on my cock, milking every last drop of semen. Then I collapsed on the girl's chest, spent.

The room span from the alcohol and exertion. I felt like I was going to pass out. But I'd done it. I'd finally had sex with Jen. Not only had I hadsex with her, I'd had anal sex with her! We stayed like that, sweaty, dirty and intertwined for some time.

Eventually, I grew softer and softer until Ifound that I was no longer within Jen's hind quarters.

Freed, Jen nudged me to the side and made a beeline for the bathroom. A few minutes later, I heard the toilet flush and the shower come on. We bathed together, for the second time that night. Then dressed in actual bedclothes and fell asleep in each others arms. I resolved to buy latex free condoms for future use, a notion which Jen appreciated.

I was, for the moment,content and it seemed Jen was as well.