Chapter 4

I stirred as I felt a sun ray cross my face. For a moment I was a bit disoriented, but then I realised where I was. Wow, it wasn’t all just a dream. I looked over at the bedside clock and saw that it was just 625am. I guess that was the flip side of having left the curtains open last night. Not that I would have traded those moments for anything.

Jillian rolled over next to me, burying her face into a pillow to shut out the light and groaning. I kissed the back of her neck gently, nuzzling against the soft fuzz at the bottom of her hairline. Her hair smelled interesting, very different than what I was used to from my wife. I felt a slight twinge of guilt as I thought of Amanda. Was I going to tell her about this? And if so, how would she take it? I quickly shut those thoughts out of my mind. I would have plenty of time to ponder them later, but for now my time with Jillian was too precious.

“Good morning beautiful”, I whispered in her ear.

She made a whiny sound and buried her head deeper in the pillow. There was a huge wet spot on the bed between us, evidence of our shared nocturnal activities. I pulled the comforter back slowly, exposing her shoulders and back as I traced my finger down from the nape of her neck down her spine. She let out a much happier sound.

“Mmm, keep doing that”, she muttered.

I pulled the comforter all the way off, leaving her bare ass open to full view. It was the first time I was seeing it in daylight and I savoured the sight, trying to commit the curves to memory. It wasn’t a Kardashian butt by any means, but somehow that turned me on even more. My eyes followed the faint tan lines from her pale hips down to where her thighs met, her pussy lips barely visible in the shadows there. I leaned foward and planted a loud kiss on each of the juicy butt cheeks.

“I love your ass”, I said matter of factly.

I heard her giggle as she rolled over onto her side to face me. Her front came into view now, allowing me to enjoy the spectacle of her slight saggy breasts with those delightful nipples that I had feasted on last night. She pushed the remainder of the comforter off me as well, leaving me naked on the sheets facing her. Her eyes drifted down to my groin where my prick was beginning to get aroused.

“Well, I love your dick”, she responded, trying to mimic my tone. She leaned forward and planted a gentle kiss on the shaft. It twitched at the contact and she giggled again.

“Jesus Georgie, I feel like a horny teenager again. All nervous and giggly about being naked with a boy!”

“I know what you mean. When I woke up next to you, I had to almost pinch myself to make sure I wasn’t dreaming. I mean, this was like the fantasies of half my teenage years.”

She grinned and wrapped her hand around my penis, squeezing gently.

“Oh really? Tell me about your fantasies Georgie”, she said sexily as her hand began to pump my cock slowly. “I love when you tell me sexy stories!”

“Oh Lord, Jillian no...”, I protested.

Still stroking me with one hand, she used her other hand to guide my fingers down to her crotch. I felt the wetness there and began to play with her in return.

“I’ll tell you if you tell me Georgie”, she continued to whisper at me. “Don’t you want to know what I used to think about when I rubbed myself?”

“Jillian...”, I protested again, much weaker this time.

She pushed my shoulder gently, rolling me over till I was lying on my back. I felt her lips kiss my nose gently and then trail a chain of kisses down my face, my chin, my neck, my chest and all the way down to my groin where my penis was now standing erect. She lifted one leg and straddled me, her wet pussy lips rubbing up just next to it. As I watched she lifted herself slightly, positioned my penis and sank down onto it with a sigh.

“Lets see if I can squeeze it out of you”, she giggled. “Go on, tell me what you used to think about when you jerked off in high school!”

I raised myself up slightly, propping my upper torso against the pillows. That gave me a much better view of and access to Jillian’s tits bouncing in front of me, as well as to the rest of her upper half. My tongue began to lick on one of her nipples.

“Well”, I confessed between licks. “Most of my high school fantasies actually involved you in some way!”

“Tell me more”, urged Jillian, her hand drifting down to her crotch in order to supplment the sensations that my dick was giving her. “Did you like to imagine me naked?”

“Oh yes”, I admitted as I sucked gently on a breast.

“Mmmmmm”, Jillian moaned as she rocked back and forth. “I used to imagine you naked too you know.”

I could feel my dick hardening at the thought. It was one thing to have my own teenage fantasies, but hearing myself featuring in hers as well was a whole new level of turn-on.

“I used to think you would be very nervous to be naked in front of me”, she continued. “I’d picture walking in on you changing and you blushed and tried to hide your pee-pee from me. But then I got to feel him up through your jeans and well, I realised it wasn’t something you could easily hide”, she giggled.

“And what about the reality?”, I asked as I switched my attention to the other nipple. “Did it live up to your expecations?”

“I love being naked with you Georgie. It just feels so right. It’s like so much was left unsaid between us back in high school, but now we’re like this there is nowhere to hide. No secrets, nothing.”

I moved my face up and kissed her squarely on the lips in response. Our tongues dueled gently while our hands ran up and down each other’s bare backs.

“You know”, I said as we finally broke for air. “It’s not the physical part of being naked that turns me on. Sure, you have a sexy body with an amazingly juicy ass, a real MILF if you don’t mind me saying so”. She giggled at that comment, as I continued. “It’s the intimacy of the situation that is the best part. Sharing secrets, baring ourselves, uh well, both physically and emotionally.”

“Jesus, it makes me so hot when you say things like that”, she said as she pulled me back into the passionate kiss. The rhythm of our lovemaking also increased as we poured our energies into each other. My hands moved down to squeeze the globes of her ass and she groaned into my mouth.

We fucked each other this time, raw primal lust taking over in contrast to our more gentle love making last night. Jillian was like a wild animal, her tongue, hands and hips all moving with a newfound energy. I thought back to what had driven her crazy last night and on a whim, ran my finger down her ass crack and pressed gently on the outside of her butthole.

Jillian screamed. Literally screamed in ecstacy. I felt her pussy muscles contracting over my pulsing cock, her juices flowing freely around my entrapped penis, and her fingers pressing into my back as she orgasmed strongly. The pressure on my shaft put me over the edge too and I spurted strongly into her, squeezing her sweaty body tightly to mine.

She lay on top of me for what seemed like days, both of us catching our breath and basking in the afterglow. I stroked her back gently, trailing my fingers down over the curves of her ass. Meanwhile, her fingers toyed with the hairs on my arm. The sunlight streamed through the window, warming up our naked bodies as we lay there silently. I felt my penis deflating inside her slowly, until it finally escaped with a gentle plop sound.

“Shit”, she said. “I’m gonna leak all over the bed if I don’t clean up.”

She swung her legs off me and stood up. I admired her bare butt again as she bounced away towards the bathroom, one hand cupped between her legs to catch any spills.

“Jesus fucking Christ Georgie”, I heard her exclaim through the open bathroom door. “Didn’t your mommy ever teach you to flush the toilet?”

I rolled myself off the bed and made my way to the bathroom. She was sitting on the toilet with her legs spread, trying to wipe stuff off her inner thighs with a wad of tissues. I leaned against the counter and watched.

“You do realise that half the stuff in that bowl was yours to begin with, right?”, I asked.

“Whatever. We both know that girl pee isn’t remotely as gross!”, she responded with a grin.

“Yeah right”, I replied as I poured myself another cup full of the hotel mouthwash. “And I suppose you poop strawberry scented rainbows too?”

“Well, lets hope you never find out!”, she giggled.

As I gargled the mouthwash, I heard the sounds of her peeing again. I looked over at her, but she stuck her tongue out at me and gave me the middle finger. It was funny how quickly we had slipped back into being so comfortable with each other. She finished wiping and stood up, once again without flushing.

“All yours Georgie”, she said, gesturing at the toilet like a game show hostess.

I stepped over and took my turn to urinate while she started to brush her teeth at the sink.

“We should order room service breakfast”, she said with her mouth half full with toothpaste. “My flight is at 2pm and the bus is leaving here at noon. That gives us a few more hours.”

“Sounds like a plan”, I replied as I finished peeing and shook myself off. “Anything in particular you want?”

“Fruit, eggs and pancakes”, she responded with her mouth now frothy from the brushing. “I need plenty of carbs to get my energy back after all this!”

I went back out to the bedroom and placed the order. They promised delivery in about 20 minutes. We set about picking up the discarded clothes from around the room as we waited. I pulled on my boxers, but Jillian decided to go with the shirt I had been wearing last night and nothing else.

Room service arrived shortly thereafter and Jillian signed for it at the door itself, blushing when she remembered that she was not wearing anything under it. I’m sure the young delivery guy sure appreciated the view in addition to his generous tip. We wheeled the cart into the room and tucked in, me sitting on the love seat and she on the desk chair that she had rolled over.

Stomach filled, Jillian leaned back in the chair with a content expression. My oversized shirt looked almost comical on her, except that it looked far sexier with the mix of covered and exposed skin.

“So Georgie”, she started. “Do you think you have the energy for one more round?”

I looked up from my last bite of toast with a raised eyebrow and another grin.

“I can try. What did you have in mind?”

“Well”, she whispered sexily as she walked over to me, straddling my lap. “Remember what we were discussing last night? The time you had permission to do anything? And nothing would be off limits?”

I nodded mutely, my heart racing now.

“Do you want to try that now Georgie?”, she asked as she blew softly into my ear. I felt my penis hardening already inside the thin cotton of my underwear, and no doubt she could feel it too.

“Try what?”, I mumbled, my mouth suddenly dry.

“Do you want to fuck me in the butt?”, she whispered with a slight giggle. “Your finger seems to enjoy playing around there after all.”

“Oh Jesus Jillian, are you serious?”

“George, I don’t know if we’re ever going to get together like this again, or if we’ll even have the chance to. I don’t want to leave here with any ‘what ifs’ hanging. I also want to know that even if it is twenty years too late, that uh ... that you were my first for something.”

“You’ve never tried this before?”, I asked gently.

“No”, she shook her head as she blushed. “I mean I know it drives me crazy when you rub your fingers around there, but I’ve never done full blown anal. Have you?”

“Not really”, I replied. “We tried some kinds of butt play years ago, I mean Anita and I did, but we never went all the way. And Amanda, well, the rear entrance is totally off limits with her.”

“Good”, she giggled. “We can be each other’s first for this!”

“Do you have any lube?”, I asked, my mind filling with a million thoughts.

“I’ve got some vaseline in my toiletry kit. It can probably do the job.”

She got up from my lap and went off to retrieve it. I just sat there, unable to believe my luck.

“So, how do we do this?”, she asked when she returned, handing me the jar.

“Well, we probably need to get naked first”, I joked.

She quickly unbuttoned the shirt and shucked it onto the floor as I pulled down my boxers. My dick sprang free, not totally hard yet but sticking out almost horizontally from my body.

“Ok, get on the bed now and stick your ass up in the air”, I instructed. She followed my directions and crawled on her knees to the middle of the bed where she presented herself to me.

“I’m just going to warm things up here”, I said as I began to kiss and caress her ass cheeks. Her legs spread wider apart as I did this, exposing her starfish for the first time. I trailed my kisses inward until I was tracing a circle right around her most private hole. I blew gently on it, feeling her squirm slightly, before leaning in and giving it a gentle kiss right in the middle.

“Georgie, are you sure?”, I heard her say hesitantly. “I mean, it’s clean right now but I do poop from there after all...”

“Strawberry scented rainbows, remember?”, I responded, using my tongue to lick all the way around the hole. I could see it twitching slightly from the teasing.

I rubbed my fingers into her soaking pussy, ensuring that they were nice and slick before returning to her backside and and rubbing them around her tight asshole. My index finger pressed against the puckered opening and it slowly gave way.