Helping Jess and Andrea

Andrea and I had had a thing, four or five years ago, way back when we still worked together.  It had only lasted about a week, but it had been a quite memorable week , and we had managed to stay good friends after without much weirdness.  We’d gone on to pursue different careers, and Andrea had become a dedicated, full-time lesbian, and occasionally we’d even dated the same girls (though never at the same time).  We were pretty close and we hung out a lot but things weren’t sexual between us at all; and (aside from the occasional masturbatory fantasy) I was fine with that.

And then one afternoon in early October Andrea told me that she and Jessica were thinking of having a baby.  She and Jess had been together over a year, and they shared an apartment.  They seemed really happy.

“Which one of you would get pregnant?” I asked over a large ice coffee.

“Ugh, not me!” Andrea said, slurping her coffee, “The idea of a fetus growing inside me kind of creeps me out… reminds me of that movie ‘Aliens’.  No, that would be Jess, absolutely.  She’s really into the idea of being a mommy.”

Jessica was cuter than hell.  She’s about four years younger than Andrea; a little shorter and a little chubbier.  They often get mistaken for sisters, which drives Jess crazy and amuses the heck out of Andrea.  To me they look like a mismatched pair of muppets, a dykey Bert and Ernie: one tall and skinny, one short and plump, both of them soft and fuzzy and kind of goofy looking with their matching black-rimmed geeky glasses.  A couple of sexy as all hell muppets.

“So listen…”

“Go ahead.”

“Well…” Andrea stirred the ice in her coffee with a straw. “We were wondering… we were wondering what you would think of being the dad?”

Wow.  That threw me for a loop.  It was so totally out of left field that I didn’t know what to say.

“Can I think it over?” I managed.

“Of course.” Andrea seemed relieved.  “It’s a big thing.  Of course you should think it over.  We’d be really honored though if you’d do it.  We talked it over for a long time. You’re the coolest guy either of us know.”

Huh, I wasn’t entirely sure that I’d ever been described as cool before.

“Would you do it by artificial insemination?”

“Are you kidding?? That’s expensive!  Besides… where’s the fun in that?”

We let it go at that, and I went home and thought about it and thought about it some more.

A couple days later, the phone rang.  It was Andrea.

“Have you thought about it?”

“Yeah, I sure have.”

“And?”

I took a deep breath. “I’d be happy to help you guys out.”

“Awesome!!” there was a pause on her end of the line, “Listen…”

“I’m all ears.”

“Next Friday is Jess’ 25th birthday.  I was wondering if you’d like to come over and help us… celebrate a little?”

Now that I had committed myself, I couldn’t wait to start.  “I’ll be there.” I said.

“Excellent!” Andrea said, “We’ll see you Friday!”

My dick was already hard.

The rest of the week crawled by.  Work was annoying.  I kept getting distracted.  And then on Friday, I had to work late.

I took the subway out to their apartment in Brooklyn as soon as I got out of the office.  It was already dark.  Andrea met me downstairs.  She was so full of nervous energy that she couldn’t stand still.

“Come on up!” she said, hopping from one foot to the other, “We’ve been waiting for you!  I mean, I have.  Jessica knows she’s getting a birthday surprise tonight, but she doesn’t know what.”

Andrea led me up the stairs, four flights up to their apartment.  She was wearing a black t-shirt and faded blue jeans, and I got to watch her cute little butt wiggle along in that tight, soft denim a few steps ahead of me.  She had the sexiest ass.  I was hoping that I’d get a chance to have another look at it soon, much more up-close and personal.

Andrea opened the front door of the apartment and pressed one finger to her lips in a gesture that meant ‘silence’.  We both kicked off our shoes in the front hall, and she took me by the hand and led me to the closed door of their bedroom.  Her hand felt small in mine, and it was hot and sweaty.

She opened the bedroom door and pulled me in behind her.  My erection was making an embarrassing lump in the front of my slacks, and it brushed against Andrea’s jean-clad ass as we slipped through the bedroom door.  She grinned at me, a nervous grin.

Jessica was lying face down on the bed.  She was wearing a blindfold and a little black party dress, and her hands were cuffed behind her back.  At the sound of us coming into the room, she turned her head.

“Your surprise is ready, my Love,” Andrea said, tugging me forward, “Are you ready?”

“I can’t wait!” Jessica said, “What is it?”

Andrea was obviously having trouble keeping from giggling.  She guided me over to the edge of the bed.  She mimed unbuttoning pants.  I got the hint and undid my slacks, letting them drop around my ankles in a heap.  I felt like a dork standing there in my work shirt, socks and boxer shorts with a prominent erection.  Andrea rolled her eyes at me and made pulling down motions.  I pulled down my boxers and kicked them and my pants out of the way.  I realized that I was blushing.  Andrea made a face and gave me a look.  I wasn’t sure what that look was trying to say.

I had never really seen Andrea and Jessica kiss before.  I mean, I had seen them kiss, casually, but not like this.  Andrea rolled Jess onto her back, still cuffed and blindfolded, and kissed her deeply and passionately.  I thought they were beautiful like that, and it made my dick even harder than it already was.

When they were done kissing, Andrea moved Jess so that she was sitting at the side of the bed, near where I was standing.  She winked at me and pressed her index finger to Jessica’s lips, encouraging her to suck it like a little dick.

Jessica is so fucking cute!  I remember when they first started dating, I had had fantasies about getting to watch just about exactly what I was watching now.  Jess stands almost six inches shorter than Andrea, five foot nothing, and has kind of scruffy short hair, big boobs for her size, glasses, and the cutest little upturned nose with a tiny silver ring in it.

She was sucking Andrea’s finger something fierce.  “God I’m horny Dre,” she said in between slurps, “God Damn I want you to fuck me cross-eyed!  Are you ready to give me my present yet?”

Andrea took her finger away and guided Jessica’s head down toward my dick.  I could feel hot breath on the head of my penis.  Her mouth was millimeters away.

“Take this in your mouth Baby Love,” she said, “Suck it real good for me.”

Andrea pushed Jessica’s head until her lips touched my waiting penis. Then Jess eagerly enveloped my cock with her hot mouth.  I was in heaven.  Andrea grabbed a big fistful of Jess’ hair, pulling her up and off my dick.  They kissed again, ferociously.  Then Jessica broke off the kiss.

“Holy fuck Andrea, it’s REAL! This is the best birthday present ever!!”

“Mmm-Hmm!” Andrea pulled the blindfold off and roughly shoved her (not unwilling) girlfriend back down onto my waiting dick.  Jessica licked and slurped with gusto.

Oh My God, her mouth felt so good, so hot and so wet, I couldn’t help moaning out loud.  Jess smiled up at me with her big brown eyes, keeping her mouth full of my cock.  Andrea was beaming like a proud parent.

Andrea pinched one of Jessica’s nipples through the black party dress, and with one hand on the back of her girlfriend’s head she forced Jess further and further down my cock, until her nose was buried in my pubes.  I was afraid that she’d gag or choke, but she never did.  I felt her swallow the end of my cock into her throat, and she kept doing the most amazing things to me with her tongue.

“Gawd Andrea, make her stop!” I wasn’t going to be able to hold out long, not at this rate, “I can’t help it.  I’m going to come!”

“Don’t you DARE come!” hissed Andrea, grabbing a fist full of Jessica’s hair.

“Mmmm-Mmmm-Mmmm,” agreed Jessica. Her boobs had spilled out the front of her dress and were shaking delightfully as she worked.  The fingers of Andrea’s left hand were busy underneath that black dress.

“Don’t you dare waste your come in her mouth!” Andrea warned me.

I felt my orgasm start in the bottom of my feet, I curled my toes and clenched with every muscle in my body.  I tried to concentrate on differential calculus.  What is the formula for finding limits?  I tried to remember the Fundamental Theorem. Jessica had lifted her mouth off my swollen dick and was looking up at me, one eyebrow raised.

I felt myself slipping over the edge, my penis twitching involuntarily, and I clenched every muscle in my body to fight down the orgasm.

One thick fat droplet of semen oozed out of the end of my enflamed cock.  Jessica grinned widely and wickedly, stuck out her tongue, and fastidiously licked it off the tip of my (almost) painfully hard erection.

“What a yummy fucking cock!” she and Andrea kissed a lot, hot and sloppy, “We’re going to have SO much fun!  Take these cuffs off, they’re chafing my wrists.”

After Andrea had fished out the keys and set wrists free, Jessica primly tucked her breasts back into her dress.  “You’ve got such a beautiful penis!” she told me, “Doesn’t he, Andrea?”

“Yeah he does!” Andrea was pulling her t-shirt up over her head.  She was wearing a lacey black bra.  Her breasts are a little smaller than Jess’, but I love how perky they are.  “It’s like the perfect penis size.  And it’s great for sucking on, huh?”

That made me glow.  I’ve always been a little insecure about my dick.  I knew my size was about average, but I guess I’ve been afraid before that girls thought it was too small.

“Is he going to get me pregnant?”

“He sure is!”  Andrea had her bra off.  Her boobs may be small, but they are just perfect in my book. They’re slightly upturned, and the nipples were pink and hard and pierced.  Steel bars gleamed in the low light of the bedroom.  That was a new addition since I’d seen them last.  “But first I’m going to stick my tongue so far up your pussy…”

She pushed Jessica onto her back on the bed.  The little black dress rode up and I caught a glimpse of black panties.  Andrea crawled on top, pulling the straps of Jess’ dress down around her shoulders, fully exposing her big beautiful breasts.  The aureole were wide and light brown.  “Aren’t they beautiful?” she asked, rubbing her own, smaller, more conical boobs against Jessica’s, “Aren’t they sexy?  I think she’s got a really nice set of tits.  Maybe later I’ll let you rub your dick all over them.  Yeah… that’d be pretty fucking hot to watch.”

Andrea slid topless down Jessica’s body.  She lifted up the black dress, gathering it around Jess’ waist.  Jessica was wearing black bikini panties with red hearts on the waistband.  Her sex swelled delightfully inside the thin fabric.  The room reeked of sex.

Jessica spread her legs wide apart, and Andrea licked all around her soft pale upper thighs, nibbling gently.  She slipped a finger inside Jessica’s underpants, and Jess moaned.

“Do you wanna see her pussy?”   I nodded dumbly.  My dick bobbed along in assent. “Me too,” Andrea said, “I want to see her pussy bad.”

Jessica lifted her ass up, and Andrea tugged, and the black panties slid right off.  Jessica had a beautiful little pussy.  Her clit was pink and swollen, straining out from under its little hood.  Her lips were swollen and puffy and pouting wide open, and slick girl-come was seeping out of her.  She was shaved, totally bare.  I’d never seen that before; I didn’t think that actual girls did that, I thought it was just what porn stars did.  She looked hot like that, soft and sexy.  I liked that I could see every little bit of her pussy.  It was beautiful.

Andrea dove right in and started licking, big loud slurps up and down Jessica’s smooth vulva.  As she licked, she fumbled with the buttons of her own jeans.

“Help me get my pants off,” she said to me over her shoulder when she came up for air.  I obliged, tugging her jeans down as she kicked her legs.  She wasn’t wearing anything underneath.  Her ass was small and pale and sexy, and her cheeks jiggled delightfully as she licked.

Jessica was up on her elbows, playing with her own nipples, tugging on them with her thumb and forefinger, hungrily watching my bobbing erection.  I think she really got off on the fact that I was there, watching them play.  Andrea was concentrating on her clit now, finger fucking Jessica’s pussy and flicking her big fat clit with the tip of her tongue.

“Roll over.” Andrea said, and Jessica did as she was told, flipping over onto her stomach.  She had a tattoo on her left asscheek, a little red devil.

Keeping her hand busy between Jessica’s thighs, fingering her pussy and clit, Andrea started licking up and down Jessica’s ass cheeks.  Jess started moaning out loud into the bedsheets.

I was sitting so close to them I could feel their body heat.  My dick was red and hot and swollen, straining up, begging to be touched; leaking a long gossamer string of clear sticky fluid.

Andrea grabbed my wrist and guided it between her own thighs.  “Stop being so damn shy,” she told me.

She was amazingly wet and slippery down there.  I slid a finger deep up inside her, finding her clit with my thumb.  She moaned, “Oh yeah, God you were always so good at that.  For a guy.”

I loved feeling Andrea’s pussy on my finger.  I remembered back to the time we had once spent together.  She hadn’t let me fuck her pussy, but we had done just about everything else.  Her pussy squeezed my finger aggressively as I slid it in and out, stroking her g-spot.

Meanwhile, Andrea had spread Jessica’s ass cheeks wide and was licking with a purpose.  I couldn’t believe I was watching this.  Jessica’s crinkled little brown asshole winked with desire as Andrea’s tongue circled around it, avoiding it, teasing it, tormenting it, and finally zeroing in on it.

As I watched, Andrea buried her face in between her girlfriends’ asscheeks.  Jessica made muffled appreciative moaning noises as Andrea slurped.  I took a chance and started gently tickling Andrea’s ass with one finger as I worked her clit and pussy with two others.

“Ok, you have GOT to fuck her right now,” Andrea announced, “I have got to see that thing of yours buried in my sweetie’s pussy!”

Jessica scooted up into doggy position as Andrea manhandled me into place.  She took my penis in her small but confident hand, and guided me to Jessica’s dripping entrance.

“Are you ready Baby?”

“Oh yeah!” Jessica replied.  Her fingers were already quite busy on her clit. “Yeah I am.  I am SO ready!”

Andrea rubbed the head of my cock up and down Jessica’s pussy.  “Fuck her,” she told me, slapping me hard on the ass, so hard it stung, “Fuck her pussy really good for me!”

I thrust forward, burying myself deep in Jessica’s drooling sex.  She was really tight inside, and very hot and very wet.  It took me a little while to get all the way in.  It was amazing.  I had never actually been inside a woman without a condom on.  It felt really good.  Really, really good.

Andrea was playing with my balls and my ass.  Every time she brushed against my asshole I jumped a little.  It felt really good, but a little scary too.

“Oh yeah, fuck her good.  Fuck her good and deep.  Oh My God you look so sexy like that!”

Andrea was masturbating as I fucked Jessica.  Jessica was enjoying the hell out of it, humping back against me and flogging her own clit.  I watched Andrea come, her fingers furiously rubbing her clit, as she watched me fuck her girlfriend.  She looked beautiful as her orgasm washed over her, making her brow wrinkle and her boobs blush pink and blotchy.

I was super turned on, and I didn’t know how much longer I could hold out.  I wanted Jessica to have an orgasm before I came inside her.

Andrea started playing with Jessica’s ass again.  The volume of her moans increased.  Andrea slid her slippery middle finger up Jessica’s butt.  I could feel it inside, pressing against my thrusting dick.  It was almost too much for me.  I stopped fucking and froze, mentally adding up the exponents of two: 2, 4, 8,16,32,64…

Andrea’s finger was sliding in and out of Jessica’s crinkled asshole, and it felt dangerously good. My poor overexcited cock twitched impatiently inside Jessica’s juicy pussy.  (4096, 8192…)

“Fuck me in the ass.”  Jessica looked back over her shoulder at me and wiggled her rear end invitingly.

I’d never done that particular thing.  I’d kind of always wanted to, I’d definitely fantasized about it, but it had never happened.  I’d always been afraid that the girl wouldn’t like it, that she’d be grossed out or think I was a pervert, or that it would hurt her.

“Fuck me in the ass.  Hurry.  Stick that cock up my butt.  Please.”  I looked over at Andrea.  She just raised one eyebrow and made a face I couldn’t read.  Her hand was still busy between her own legs, where she had a couple fingers making squishy noises caressing her own pussy.

I pulled out of Jessica’s pussy.  My cock was coated in her juices.  It looked really sexy.  Andrea gave me a quick peck on the cheek and fetched a little bottle of lube from the bedside table.  She dribbled a liberal amount of the clear fluid onto Jessica’s anus, and then guided my very slippery cock up against her girlfriend’s horny little asshole.

“Give it to her gently,” she said, “Our regular toy’s a bit smaller.”

“Yeah, give it to me hard,” Jessica said, “I want it, please.”

I pressed into her.  She pressed back against me.  Her ass opened up, and slowly, very slowly, my dick disappeared inside her.  She was unbelievably tight, almost painfully tight.  Andrea watched, wide eyed, as I slowly worked my cock all the way up Jessica’s tiny little butt.  I don’t know how long it took.  Jessica made a lot of noise, but it sure sounded like she was enjoying herself.  Her finger kept busy on her clitoris. At last I was all the way in.  My pubes were pressed against her asscheeks.  It felt like my dick was being grasped tightly in a strong, soft fist.

“Does it hurt?” I asked

“No it doesn’t hurt at all.  It feels so fucking good.  Fuck me.  Be a little gentle, but fuck me hard!”

What?  I decided not to worry too much about what that was supposed to mean.  I was way too turned on to puzzle that one out.

Andrea slithered around to the front, presenting Jessica with her wide open and sopping wet pussy.  She has a really sexy pussy too, with nice fat lips and a neatly trimmed brown bush.  Jessica dived in, moaning out loud into Andrea’s puss, lashing it up and down with her tongue.

I started fucking Jessica’s tight ass, slowly at first, then harder and faster.  The harder I thrusted, the louder she moaned, and they definitely sounded like happy moans to me.  I wasn’t going to be able to hold out much longer.  I reached under her belly and slid my middle finger up into her pussy and rubbed her clit with my thumb as I fucked her ass.  She was getting so loud that it was almost scary.  I felt her come, her ass spasming on my dick, her pussy squeezing my finger.  It set me off, and pounded her rump hard until I came deep inside her asshole, my cock twitching and spurting out what seemed like gallons of come, while I shouted her name out loud as her ass wiggled and bucked under me.

Later, when we were all showered and cleaned up and more or less dressed, we all sat down together on the couch.  Andrea had cracked open a bottle of wine.

“Mmm that really was the best birthday present ever!” Jessica said, snuggling up to Andrea and giving her a big wet kiss.

“I’m glad you liked it sweetie,” Andrea said, “That was really hot.”

“Yeah it was.  It’s been such a long time since I’ve played with a boy.  You’re a really fun one,” she said to me.

“Thanks.” I said.

“But you know what?  It’s going to be kind of hard to get me pregnant like that.”

“Well we’ll just have to keep on trying now won’t we?” Andrea said, sipping her wine, “We’ll keep on trying until we get it right.”

2 Comments »

  1. Elsie Fan(ny) said

    This is another of your great stories. I especially like the implied “to be continued…” in the last sentence.

  2. icam said

    this story is like a warm cuddle, in porn form
    cheers 🙂

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