A Good Time With Stacy Ch 05

Author's note: Thank you for your comments and I hope that you enjoy the next couple of chapters in this story. I will finish this story, but please, keep posting you comments. I love reading them.

######

Les and I were having regular sex and on one occasion I was giving Les a sloppy teabag and blowjob when my saliva dribbled down his perineum. I held his balls and gently massaged them using my saliva to slide my fingers over his scrotum. I slowly moved my fingers down his perineum and when I knew he was close to coming, I pressed my finger against his anus.

"Oh... fuck," said Les, as my finger twirled around his sphincter and slowly entered his anus.

I guessed that he liked what I was doing, so I masturbated him with one hand as I massaged his balls and fingered his bum with the other. He came within seconds and he shot his semen all over his belly and my fingers.

I let Les rest as I washed my hands and returned with a wet face-washer for him to clean up his mess. Fingering Les's bum became a regular part of our sexual repertoire.

~~~

Besides having a few friends from work and neighbours, there were three groups of people that I tended to mix with: people in Les, my boyfriend, and Brad's, my best friend Stacy's boyfriend, bicycle riding group, who were really nice people; some people involved with the theatre group, who had great parties after performances, and students from the Teacher's College, who had great parties, which Stacy and I, and sometimes Brad and Les, often attended.

One such party, with the students, was a fancy dress party. We didn't go to too much trouble: I suggested that the boys wear a summer dress each (because they already epilated their legs) and Stacy and I wore bikinis and kids, luau, hula skirts with lei, which we bought from Woolies for a couple of bucks. We got stoned, before arriving at the party, and drank some alcohol. Many people slipped out for a bong or joint and Stacy and I often joined them.

We had a great time and some of the costumes were really well thought out. One fellow wore a T-shirt with bullet-holes drawn on it and little round glasses -- it was just after John Lennon's death. There were two, different categories of responses: some people thought it was too soon and others thought it was really funny. I was in the latter group.

The four of us agreed that we would make a better effort with our costumes at the next fancy dress party.

Les and I arrived home from the party, fairly inebriated and horny. He was still wearing my old, summer dress and I imagined Les being a woman, so I asked him, "Do you like anal sex, Leslie?" [Note my use of the female form of Les's name.]

"I'll give it a go, if you like," answered Les.

I surprised him by putting on my strap-on harness, with the small dildo jutting out from my pelvis.

"Oh..." said Les, "I thought you meant different anal sex..."

"Why would I grant you that access if you haven't granted me yours?" I asked.

"Don't worry, I won't hurt you and, besides, you're dressed for the part."

Les looked at my summer dress that he was wearing. He wasn't wearing anything else feminine: no makeup; no bra; no other clothes, besides his male underpants and his sneakers. I didn't give him much time to think: I kissed and hugged him passionately and my hands groped his buttocks. My fingers spread his cheeks and my right, index finger crept closer and closer to his anus as I groped his globes.

Les's penis hardened against my abdomen as I kept poking at his anus so I pushed him backwards onto the bed. I grabbed a condom and rolled it onto my phallus. I pulled a disposable, latex glove onto my right hand. I grabbed the personal lubricant from the bedside drawer and Les became fully erect as he watched me lubricate my gloved fingers.

"On all fours, baby," I said, as I crawled onto the bed. Les immediately rolled over onto his knees and elbows.

I ran my fingers along his smooth calves. He looked like a woman in a dress from where I was kneeling so I lifted the hem of his dress and sighed, in disappointment, when I saw his manly boxer-shorts. Next time, I'll have to dress him in sexy panties.

I pulled down his undies and he lifted his knees and then feet to allow me to strip them off him. Now, with the hem of his dress up on his back, he looked more like a sexy woman ready to take it doggy-style.

I spread his buttocks with one hand as I twirled my index finger around his anus. I watched his anus pucker and dilate in anticipation. I pressed the tip of my finger against his anus and his sphincter immediately relaxed to allow access. I smiled and then twirled my finger as it penetrated his rectum.

Les gasped as I pressed my finger against his prostate. His sphincter relaxed more so I pushed another finger into his bum and Les groaned. Les lowered his head onto the pillow as I gently fingered his prostate for a few minutes but I didn't want him to come; not yet, anyway.

He grunted when I pulled out my fingers and I generosity lubricated the small dildo protruding from my crotch. I placed the glans against his anus and slowly pushed. Les gasped and slid forwards until his head hit the bedhead as the glans penetrated his sphincter.

"Please be gentle," whispered Les.

"Yes... at first..." I answered.

I slowly moved my hips, backwards and forwards, as my phallus slowly worked its way into Les's anus. Soon my hips were gently bumping against his buttocks. The length of my thrusts slowly increased and soon the full length of the small dildo was sliding in and out of Les's anus. I thought of pegging Stacy for a fraction of a second but then concentrated on Les.

"Are you okay, baby?" I asked, as I slowly increased the rate of my thrusting.

"Yes," gasped Les.

That wasn't enough for me, so I asked, "Are you sure?" as I thrust into him, faster and faster.

"Yes," said Les, louder, "It feels... good..."

"Just good?" I asked, as I held his hips to give me better purchase.

That, somehow, opened up Les's vocabulary. He gasped, on each thrust, "It feels... very... good... It feels... terrific... tremendous... brilliant... wonderful... glorious... marvellous... heavenly... fantastic... epic... phenomenal... magnificent..."

"Are... you going... to come?"I asked, in between thrusts.

"I think so," answered Les.

"Touch yourself... baby... Make... yourself... come," I suggested.

"OH... FUCK!" yelled Les, as he appeared to come.

But I wasn't finished. I kept thrusting, rubbing my clitoris on the harness and the bigger dildo inside me stimulated my vagina. I was really close to my own orgasm.

"Oh... god..." said Les, as I kept thrusting

"Do you like being buggered?" I asked, somehow Les's enjoyment was contributing to my imminent climax. My body tingled with heat as my orgasm arrived.

"Yes... yes please... I'm so close..." answered Les, as his body squirmed.

I almost lost consciousness as I came but I kept thrusting.

"I'm... coming... again..." declared Les, as his body bucked. "Oh... Bradley..." whispered Les, as he collapsed onto the bed with me on top of him.

I laid on top of Les, catching my breath, and trying to interpret what he just said. Was it 'Bradley'?

I rolled off Les and he groaned as the dildo slipped out of his bottom. I gazed into his eyes and saw his shameful expression. I waited for an explanation but received none. I needed to know if I heard him correctly. "Bradley?" I asked.

Les blushed and looked away, and although he looked cute, I needed answers. "You're not in trouble," I said, as gently as I could. "I just want to know."

Les looked me in the eyes and nodded.

"Did you... um... imagine... that Brad... was... buggering you?" I asked, benevolently.

"I... I don't know..." answered Les, unconvincingly. I kept looking at Les until he answered, "I think so but its... you know... a fantasy."

"Yeah, I get it," I lied. I caressed Les as lovingly as I could and he seemed to relax.

I pulled the condom off the dildo -- it was much easier to take a condom off a flaccid penis -- and threw it in the bin. I took off the harness -- it was so nice to feel something still hard being pulled out of my vagina -- and stored it, ready to be washed.

I handed Les some tissues and he cleaned up most of the mess. It was nice of him to try. Other men would just clean themselves and leave the rest of the mess for me to clean. "Thanks for cleaning up," I said, with a relaxed smile.

"You're welcome," said Les. "Um..." he said, as he indicated my dress that he was wearing.

I chuckled and said, "I'll wash it. Who knows what damage you'll do to it if I let you wash it."

Les laughed and changed into his casual clothes that he wore before getting changed for the party. I was so glad that he understood my sense of humour. He left and I masturbated to help myself get to sleep.

~~~

The following Friday, as we were eating dinner, I mentioned to Stacy that I'd pegged Les -- I didn't mention his reference to Brad. She asked, "Do you think he enjoyed it?"

"Of course," I answered." Why wouldn't he?"

"I don't know," answered Stacy. "It's... not... natural..."

"Are you kidding me?" I asked. "Lots of mammals have anal sex so why wouldn't homo sapiens?"

"Does it feel good?" asked Stacy, and then I realised that she was an anal virgin.

I needed to be honest with her, so I answered, "Well... with the right... partner, who's considerate, I find it very... um... stimulating." I gazed into Stacy's eyes hoping that she would take the bait.

"Are you a considerate, anal partner?" asked Stacy, with a twinkle in her eye.

"I think so," I answered, hoping that she'd agree.

Stacy leant across the table, held my hand and asked, "Would you like to take my virginal bum?"

I smiled, and answered, "I'd love to."

Stacy leant back into her chair, and said, "Well then... we'd better finish dinner," and smirked, coyly.

Stacy laid, naked, on the bed as I donned the harness with the small phallus poking out from my groin. I rolled a condom onto the phallus in preparation and looked at her waiting for me to do something.

Her body was so beautiful: there's something about the feminine curves that makes a woman beautiful. There's probably a formula to explain the change in radii, maybe quadratic? But it didn't matter. Women's bodies are just... so... beautiful.

"Roll over," I said, and Stacy rolled onto her belly, exposing her curvaceous back end. The sex-blanket was underneath her, ready to absorb the consequences of our activities, so I generously lathered her buttocks with personal lubricant. Stacy sighed, as I massaged her buttocks. She spread her legs in anticipation when I reached her thighs, but I didn't touch her crotch -- that was an objective for later.

My massaging progressed to spreading her buttocks, wider and wider, exposing her beautiful anus. I watched it ruck up and then relax as it was exposed. I blew on Stacy's anus and it almost retracted. Stacy gasped, "Don't... um... lick there... I haven't... recently washed."

I smiled at her bashfulness and that she hadn't fully rejected the idea of anilingus, she's just attached conditions -- that'll be another treat for later.

I kept Stacy's buttocks spread as I kept blowing on her anus. Soon she was conditioned to relax with that gentle stimulation, so I dribbled lubricant onto the top of her cleft and watched it slowly flow towards her anus. Her anus relaxed as the lubricant flowed over it and I cupped lubricant with my fingers at her perineum before it reached her vulva. I slowly slid my fingers upwards and gently touched her anus, as I spread the liquid between her cheeks.

At first, I touched her anus ever so softly, but once she became used to my contact, I applied a little bit more pressure, each time my fingertips passed over her anus. Soon Stacy was lifting her pelvis, each time my fingers passed over her entrance, trying to encourage further incursion. I smiled.

Stacy gasped as I changed tactics and slowly twirled my fingertip over her anus. I was having fun with Stacy's impatience so I postponed penetration and gently tapped her anus with my fingertip, as if I was knocking, asking for entry. Each time I tapped on Stacy's anus it would pucker. Minutes later it just dilated. I now decided to concentrate on the objective.

I tapped my finger onto the middle of Stacy's anus and held it there. My finger had ever so slightly penetrated her anus so I twirled my fingertip in the little indentation. I applied slightly more pressure and Stacy's sphincter adjusted to allow access. Soon my finger was slowly twirling against her orifice. Her sphincter resisted so I pressed just a tiny bit harder. I held my finger against her sphincter's resistance until it fatigued and allowed my finger entrance. Stacy sighed as my fingertip passed through her sphincter up to the first knuckle. I held my finger there until her sphincter relaxed again and my first knuckle passed through.

"Are you okay?" I whispered.

"Yes," sighed Stacy, as I felt her sphincter pulsing around my finger.

I turned my finger around in her anus, without pushing any further. Stacy sighed with each breath as her sphincter relaxed, so I added pressure as my finger rotated inside her.

"Oh," sighed Stacy.

I let her become used to the invasion and once she'd become acclimatised to the intruder, I slowly pulled my finger out until my first knuckle passed out of her sphincter. I paused before pushing my finger in again, past that first knuckle. I slowly repeated the process until her sphincter showed no sign of resistance each time my knuckle passed through it, so the next time I pushed, I kept going until my second knuckle passed through her sphincter.

I had my finger deep inside Stacy's anus so I slowly turned it clockwise and anticlockwise until her sphincter relaxed again. I then slowly wiggled my finger, in a come hither motion, hoping that I was pressing against her G-spot through that thin membrane between her rectum and vagina.

"Oh... frig..." gasped Stacy and I smiled. I think that she liked what I was doing.

I kept wiggling my finger and then added an in and out motion until, after a few minutes, I was definitely thrusting my finger, in and out of Stacy's bum.

"Oh god," gasped Stacy.

I still felt a slight resistance to my finger, from Stacy's sphincter, as I kept thrusting. However, after a few minutes of constant thrusting, Stacy was pushing back, on each thrust inwards, and pulling back, on each outwards motion.

Stacy was humping my finger so I added sideways pressure to stretch her sphincter. I soon saw a gap around my finger as I kept thrusting and so I pressed my middle finger against Stacy's anus. She stopped humping as I stopped thrusting and she allowed me to slowly insert a second finger into her anus.

"Oh... bugger..." gasped Stacy, as my two fingers penetrated her.

Noting Stacy's reluctance to swear, unless she was in the throes of orgasm, I said, "Soon, Honey... soon... I promise."

Stacy's sphincter relaxed around my two fingers so I slowly thrust them in and out. Minutes later I was thrusting, twirling, rotating and pulling my fingers against Stacy's anus. She was thrusting backwards and forwards against my invading fingers. She lifted herself onto her knees and violently thrust against my fingers.

"OH... FUCK!" cried Stacy, and I felt her anus throbbing around my fingers as she sat back onto her haunches, trapping my hand under her and my fingers deep inside her anus.

Stacy slowly rotated her hips on my fingers as she rode out her first climax. Her anus stopped throbbing and she started to rise up and down on my fingers.

I pushed Stacy forwards as I kept fingering her bum and she kept thrusting against my fingers. She was really into anal, so I flipped the cap off the lubricant and spread the slippery solution over the condom encased dildo, extending from my crotch.

I positioned myself on my knees behind Stacy. I pulled my fingers out of Stacy's bum and she demanded, "No... more... please."

I held her hips as I pressed the glans of the dildo against her anus. I said, "This is a bit bigger than my fingers. It might hurt a little bit."

"Give it to me," demanded Stacy.

I pushed forwards and Stacy's sphincter resisted. I held still as the glans pressed against her indentation. I let Stacy control the penetration; she slowly pushed back and wriggled her backside. She tilted her hips, up and down, as she pressed back onto the dildo. She gasped as the glans slipped through her sphincter. Her body trembled as she waited.

I watched the glans slide in and out of Stacy's anus as she slowly moved backwards and forwards. She then moved further backwards than forwards, on each thrust, and I watched, in amazement, as the dildo slowly progressed deeper into Stacy's rectum.

Stacy ground her buttocks against my hips when the little dildo was fully buried deep inside her. She slowly pulled forwards and the dildo emerged from Stacy's anus. She slowly pushed backwards and continued to bugger herself on the dildo.

"Fuck me, Honey. Fuck me hard," demanded Stacy, as she kept thrusting against me.

My puritanical Stacy had become an anal slut, but who was I to deny her pleasure, and maybe I'd get a bit of stimulation too. I grabbed Stacy's hips and obeyed her command. I rammed the dildo in and out of Stacy's rectum.

"Oh... YES..." cried Stacy, as I pistoned her like a steam train driven at full speed. At first Stacy braced herself against the bed head but then she thrust back against my thrusts. Stacy grunted each time the dildo rammed into her and she started to violently pigroot.

"FUCK YEAH!" yelled Stacy, uncharacteristically.

I touched her clitoris with the fingers of my left hand and she violently climaxed. Not only that, I felt her squirting over my fingers as she thrashed around in orgasm.

Stacy collapsed onto the bed and I collapsed on top of her. She grunted as my weight pressed the dildo deep inside her rectum. She feebly pushed against my hip so I slowly lifted myself off her and she grunted as the dildo slipped out of her anus.

I collapsed into my back, pulled the condom off the dildo and disposed of it. I released the harness straps and wrapped it the sex-blanket.

Stacy rolled onto her side to face me, and asked, "Did you come?"

I frowned, and honestly answered, "I don't know. I certainly enjoyed myself. Did you?"

"Oh yeah," answered Stacy. "That was... brilliant. No wonder guys like being pegged. I'm going to have to peg Bradley."

"Maybe ease him into it with some anal fingering," I suggested. "Guys are sometimes unwilling to have anal sex. They might think that it subverts their masculinity."

"Okay, I'll keep that in mind," said Stacy.

We laid there in silence, happy with each other's company without the need for conversion. Soon I drifted off to sleep.

~~~

Stacy later confided in me that she did peg Bradley and he liked it. She also allowed Bradley to bugger her but he always wore a condom no matter what form of penetrative sex they had; she didn't like that messy stuff inside her. I revealed to her that I also didn't like semen inside any of my orifices.

~~~

We were invited to another party, with the theatre group, to celebrate the end performance of a successful play. Stacy and I were invited because we volunteered with painting and setting up the stage.

It was a cross-dressing party, because the play had a bit of a cross-dressing theme, and we were determined to make a big effort with our costumes. We were fortunate that we didn't have to buy many clothes: Stacy and I wore Brad and Les's suits, respectively, and Brad and Les wore some of Stacy's and my clothes, respectively.

We ladies didn't have to go to much trouble: we donned the men's clothes; drew moustaches on our upper-lips, stuffed the men's, business shoes with tissues, so that they'd fit us, and pinned up our hair under bowler-hats that we'd bought from Vinnies.