Chapter 3: Undercover at the April party

I had gotten myself a pass for the late afternoon lecture – I said I had a family meeting – and as I was more than up to date on the assignments, the professor said it wasn’t a problem and emailed me the lecture notes. I’d carefully clean shaved that morning, was wearing my new shirt, and by five o’clock on 4/6, I was parked up outside a strip mall three blocks from home.

At quarter of six, I drove into our drive and parked my car well away from the house, where it couldn’t be seen and recognized from the windows.

I got lucky as another car pulled up while I was walking to the door, so I immediately pulled out my mask from my jacket pocket, and was therefore already wearing it and stripping off my clothes when a couple of strangers entered the hall. I picked up the male number 4 wristband, and shared my test results with them. As they bent over their boxes to pack their clothes away, I ‘borrowed’ a blister pack of six Cialis from my Dad and put it in one of my shoes, covering it with a sock. He could sure afford it, I had an idea for making good use of it, and I reckoned it was a very small part of the debt he now owed me. Then I headed upstairs.

I was looking out my (curtained) bedroom window when Laura and Jessie drove up to the house at twenty past six, in Laura’s car, and parked in front of the garage. It was a very simple matter to be downstairs in time to meet them as they came into the hall. Jessie was smiling and looking great, as was Sis.

“Hey, Jessie, I’ve been looking out for you, just like I promised. It’s really great to see you again!”

I hugged her, and she kissed me back.

“Hi, Michael, you too. Remember my roomie, Laura?”

“Of course! Nice to see you too, Laura.”

I gave my sister a peck on the cheek. She turned my head and kissed me on the mouth.

“Jessie says you were the one who carried me up to bed last time, so thanks a lot for doing that. I was pretty wasted. She was hoping that you’d be here.”

“It was no trouble. Damsels in distress my specialty! And I promised, pinky oath, that I would be looking out for her tonight.”

They both giggled. Yeah, the Noo York accent did clash a bit with the words. You can’t imagine Robert de Niro in ‘Taxi Driver’ saying ‘damsels in distress’, can you? Maybe ‘dames in trouble’?

They started stripping and picked up their wristbands; they were pink numbers 10 and 11; the male tallies were now up to 8. I saw that they both popped a Cialis, and then got out their test certificates. I picked mine out of my box, and we checked dates, smiled, and put our papers away. I didn’t fail to notice that they had also folded them so the name wasn’t visible – it would kind of make a mockery of the anonymity of the masks if you then showed your name and address at the door.

The Cialis I had taken earlier, and the proximity of two beautiful and naked girls quickly had my cock standing erect and proud. I’m pretty sure that I caught the two of them exchanging grins as they finished packing their clothes away and donned their masks.

I told them, in my very best antebellum Confederate Gentleman accent, that I’d allow it as a huge honor if they would kindly allow me to lick their little kitties some. They giggled again, and Jessie focused her inner Southern Belle as she said that they’d be totally delighted...

As we went up the stairs together, I heard the house door open. We’d just got away before the next guests arrived, so no-one knew that that I’d snared the two loveliest girls first. Laura led us to her bedroom, which was perfect for my purposes. I shut the door behind me, which I had read was considered a polite request for privacy at these sex parties. I didn’t want to be disturbed until I’d had my wicked way with both of them – Jessie for the sheer joy of it, and Laura as a bit of fun, and a bit of unspoken retribution for holding out on me.

Jessie was openly grinning; I guess, like me, she was remembering how we’d started off the previous time. Personally, I hoped that I would be able to recall the sheer joy of that coupling even when I was old and gray. It had been, without a shadow of a doubt, the best sexual experience of my life so far.

I took her into my arms first, kissing her gently, and then moving down to place a kiss on each of her nipples, her belly button and her butterfly tattoo. Then I turned to Laura and did the same to her; they both giggled when I got to her tat.

“God, you two are SO totally gorgeous!”

They smiled at the compliment. Jessie retorted that I didn’t look too bad either, which earned her a kiss on the nipple.

“Why don’t you kiss Laura, Jessie?”

She did, spending longer on the mouth kiss than I had, and then Laura did it to her. Of course, that then gave them ideas, and they took turns to kiss my mouth, nipples and cock. I wasn’t about to complain. Jessie looked inquiringly at me, and I held out my palm to her, to suggest that it was her I was addressing, rather than Laura.

“Which of you lovely ladies is going first?”

“I suppose that it’s only fair if you start on my roomie this time? You are going to fuck both of us, right?”

“I hope to do exactly that! In fact, it will be an honor and a pleasure! But I’m sure going to munch both your muffs first!”

They both giggled. Laura laid down on her back in the middle of her bed. I got down between her legs and took a good look at her pussy. Yeah, it was sure good enough to eat. There were drops of moisture on her pink and swollen labia already.

“You didn’t start without me, did you?”

She giggled again.

“No, but we were talking real dirty on the way over. My panties were soaking wet when I took them off!”

The anticipation had done Sis no harm at all. I used my thumbs to open her outer lips, and the white skin gave way to the lovely pink texture of her internal tissues. Her juices were all ready for me to lap up, and her little soldier needed no coaxing to emerge from her sentry box. Yeah, as I’d thought, real good pussy. The fact that it was forbidden fruit being plucked unknowingly excited rather than repelled me. Yeah, I could do this incest stuff with Sis. My cock was hard as nails.

I felt movement on the bed beside me, and Jessie crawled over Laura so that she was straddling her roomie’s shoulders.

“Laura, just so you don’t get bored, you wouldn’t look after me a little, would you?”

Sis reached up and pulled Jessie’s legs so that her pussy was just in the right place, and started licking. I got a great view over Sis’s flat toned stomach, between the soft rounded cones of her tits; and I have to admit that I wasn’t fully concentrating on my own task while there was such an erotic sight in front of me. Sis was reaching up with her tongue to tease Jessie’s darker lips apart, and as Jessie rocked to allow the best access to her goodies, I could see the contrasting pink of her inner lips and vagina.

Man, was Sis already turned on! I got back to what I was doing, and within a couple of minutes, her belly started moving rhythmically, her thighs tried to crush me, and with a gasp and a muffled squeal, she got there. Jessie was no longer sitting on her face; she was kissing her roomie passionately. I watched for a minute as they necked; remembering what Jessie had told me about her relationship with her roomie. Yeah, it was certainly more than fuck buddies – there was a loving affection there as well. I was torn – I was pleased for Sis that she’d found someone like Jessie, but also jealous, as I’d have loved to have Jessie as my girlfriend.

They moved apart, both breathing heavily. I took the opportunity to move up Sis’s lovely body, sticking the tip of my tongue into her belly button, grazing on her erect nipples with my lips and teeth, and then made nibbling kisses all along her neck up to her ear. She was rubbing my arms and back with her hands, panting in anticipation.

“Why don’t you go on top first, and then once we’re comfortable, I’ll do the work?”

She grinned and nodded. I rolled off of her and laid on my back, and Laura knelt up and lifted a leg over me, then squatted down over my belly, reaching behind her for my cock. She spat some saliva into the other hand and rubbed it onto her pussy lips to help with lubrication.

My sister was about to actively fuck me for real, one on one, not as part of some other action. My cock, already diamond hard, jumped at the thought.

I was real pleased that I had decided to jerk off in the shower that morning; if I had been more sensitive, I’d probably have popped off prematurely with the excitement. As it was, I was able to resist the initial urge and just enjoy the sight as she placed me in position.

She gasped as my cockhead passed her outer barrier, and then sighed as it parted her tender tissues. Then she slid down, murmuring to herself, until she was fully impaled. She grinned at me.

“It’s been a long month! We’re ready for some real cock!”

I smiled back, reaching up to caress her breasts. Yeah, they were as soft, firm and delicious as I’d remembered.

“For me too! I’ve been dreaming about you two!”

“Well, let’s just see if we can make our dreams come true!”

She rocked experimentally, gave a satisfied sound, and put her palms down on my chest to give her leverage as she started rolling and flexing her hips.

Jesus! Where had my sister picked up a technique like that? It felt amazing, and she seemed to be doing it almost effortlessly. Luckily for my reputation, the sensation was great, but it didn’t seem to be about to make me spurt. She gave a few moans of pleasure and her top teeth gripped her lower lip in the expression of concentration I’d seen on her face thousands of times as we grew up together.

She paused for a moment, then started sliding up and down my pole at a much more rapid pace; she had great control over her thighs, and she was using most of my length. It felt incredible.

She started gasping for breath, and I could see the pale skin of her breasts and neck beginning to glow pink, and then all of a sudden she jerked and screamed, and almost lifted off of me before plunging back down on me and collapsing on my chest as she shuddered through her orgasm. I put my arms around her and held her tight, kissing her hair.

Wow, just wow! I’d thought Laura would be just a fun fuck, but as she lay in my arms and regained her breath, I realized that she came very close to Jessie as a top quality lay. I’d been more than lucky not to shoot as her cunt convulsed around my dick.

After a couple of minutes of closeness, she sat up again and moved her hands over the muscles on my chest and arms.

“You work out, don’t you?”

“Not too much, just enough to stay fit. There’s a gym in the residence basement.”

“Very nice. I like a man with muscles. Could you lift me?”

“Of course I can; I carried you upstairs last time.”

She giggled.

“I didn’t mean it like that. Have you ever fucked standing up, face to face?”

I’d once fucked Amy from behind over her desk, that didn’t count.

“No, I haven’t.”

“Me neither. Want to give it a try?”

She dismounted, we got off the bed, and stood together, neither of us quite sure what to do next. She took the lead.

“Michael, if you stand with your legs well apart and your feet braced, I’ll try to climb up. If you lose your balance, try to fall on the bed, rather than the floor, willya?”

“Put your arms around my neck, and lift up one of your knees, and then I’ll try and give you a boost up.”

We did that, and she had my dick between her legs, but not quite in the right place. Jessie deftly sorted that out, and between the three of us, we lowered Laura down until she was fully impaled. She squeaked as she hit bottom.

“Christ, Jessie, this feels amazing! If he splits me up the middle, girl, it was good knowing you!”

We tried lifting Laura up and down on my dick a few times; she also did her hip flexing which also worked, but it was clear that it wasn’t going to go much further without a bit more thought. She wasn’t comfortable, and neither was I.

“Sorry, Laura, I don’t feel that I’ve got you safely. This position could be truly awesome, but I think I need to watch some porn and work out how to do this without hurting you. Can I give you a rain check on this one?”

She giggled and put her face up to kiss me on the lips.

“Yeah, it doesn’t feel right. It’s a bit on the discomfort end of the feeling full scale. Jessie and I will do some research as well, and then you can do both of us this way at another party.”

Jessie and I helped her off, and she gave Jessie a long and lingering kiss with tit-rubbing before returning to the bed. I was lost in thought and stood there for a couple of minutes.

“Laura, I think I might have an idea. Jessie, please keep her ticking over while I check out the bathroom.”

I knew that there was a stone-topped counter in Jessie’s bathroom; several years ago, Dad and I had helped the contractors get the heavy slab up the stairs and on to the lumber framework. That was a serious bit of construction, and it would probably be perfect for my needs. At thirty inches deep, it was a little wide, but I had a possible solution for that. Once again, there was an ample pile of the laundry service white towels; someone had been clearly busy putting them out in the bathrooms ready for the party.

I laid a towel down on the stone, and went back into the bedroom. The girls were in a sixty-nine with Jessie on top, and I watched for a couple of minutes as they enjoyed each other, then moved close enough to run my finger into Laura’s pussy as Jessie’s tongue attacked her clit.

“Okay, girls, I’ve got a solution that might work.”

I led them into the bathroom, got Jessie to sit far back on the counter with her back against the big glass mirror, and then asked Laura to sit between her legs. Jessie ran her hands under her roomie’s armpits and began to caress her tits – did I mention that she was a bright girl? Laura sure liked the extra touch.

That didn’t quite work for me; Laura was too far back. I put a rolled-up towel behind Jessie to bring Laura’s pussy to the edge of the counter, and then I spread her legs as wide as I could get them. I set my feet firmly, swabbed the head of my dick in her juices, and drove home in one long slow thrust. She gasped as my pubic bone crushed her clitty, and I held there for a moment, moving ever so slightly so as to keep up the stimulation.

Actually, that seemed like a great idea, so I stayed where I was and did a little hip rotation and sideways motion. Yeah, good choice, bro, she LIKED that. I must have spent the next ten minutes doing variations on that, occasionally pulling out so that she could enjoy again the sensation of being entered and filled in one long slow thrust. Twice I squatted down and licked her from perineum to clitoris; that got great audience reviews too. She had a couple of decent cums, and then I decided to go for it, put my hands under her thighs on the edge of the counter, and hammered away at her pussy.

She screamed into my ear as the bliss of a huge orgasm bit her senses; her body was wracked with tremors, and the churning of her insides gave my dick no choice but to erupt. That made her scream with delight again.

(I hate to admit this, but I breathed a short prayer of thanks to Amy, who’d taught me a great deal more about pleasing a woman that I hadn’t picked up at high school. Those techniques, along with the infallible ones of plenty of foreplay and eating them out, had helped me satisfy both Jessie and Laura, and I’d have been real pissed with myself if I’d left either of them hanging.)

Then I moved my hands to her lower back, lifted her up off of the counter still impaled on my dick, and with only minor wobbles on the way, carried her back to her bed and lowered her down. My dick popped out of her as I straightened up, and she grunted with dismay at the loss. I dropped down beside her and kissed her. She snaked a hand around my neck and kissed me back.

“Jeez, Michael, that was a GREAT idea!”

Jessie cuddled in and hugged both of us. We enjoyed the closeness for a few minutes before she reminded me that I still owed her.

“Now it’s my turn to have my pussy eaten!”

Sis rolled over to one side, Jessie took her place and I moved back to admire her lithe mocha-colored body before I dropped down again to kiss her on the lips, on the neck and then further down.

I suckled on her dark nipples, rolling my tongue around them and nipping them with my lips until they became almost impossibly distended with the blood in their erectile tissue. By the time I got to her pussy, the licking that Sis had already given her, coupled with the arousal from watching (and feeling) me fuck her roomie, had made her very wet. It didn’t take more than a couple of minutes of me licking her pussy and Sis working on her breasts to have her loudly signaling an orgasm.

We didn’t need to speak to know that she was more than ready to fuck, so I rolled onto my back in the center of the bed and she climbed on. Having already shot off my first load in Sis, I was confident of lasting longer with Jessie. After she’d ridden me to her second climax, she turned onto her side and pulled Laura into a close hug. I lifted up her leg and slowly fucked her from behind while her tongue fought with Laura’s, and their tits rubbed against each other. She was soon at another peak, arching her back to try and take even more of me, and when she came down from that one, she rolled onto her back and told me to fuck her until I got my own nut.

So I did.

With Laura urging us on, I pinned her roomie down and tried to drill my dick through her and into the mattress. At every thrust I jerked my hips so my pubic bone crushed her little clitty, and each time was rewarded with a gasp of pleasure. She wasn’t just lying there passively, oh no; she was moving her own pelvis back up towards mine so that they collided at maximum pressure. It was exhausting and exhilarating; but it only lasted a few minutes before she spasmed around me and screamed out another orgasm, and twenty-odd thrusts later, I groaned as I hosed down her cervix. Then I almost collapsed on her, just managing to roll my torso to one side so that we could both get some air into our lungs. It was a toss-up as to which of us was breathing more heavily.

Once again, she’d really gotten into it, and her enthusiasm had helped me give of my very best too. Laura wriggled her way onto us, and we nuzzled and stroked, enjoying our post-coital euphoria for a few minutes, until Jessie started to sit up.

“Thanks, Michael, that was another great start to the evening!”

I grinned.

“Me too! Still can’t quite believe how great you two are together!”

We stood up. The moment of shared intimacy was almost over. I hugged Jessie, and then Laura, and then the two girls embraced. Laura finished kissing Jessie, and then turned to me.

“Thank you, Michael! It was so hot with you fucking both of us! I really liked it on the counter! Can we do it again sometime soon?”

Wow! Sis wanted to do more of this? So did I! I tried not to get too obviously excited. Keep cool, Mike, pretend that it’s only great sex.

“How ‘bout next month? Will you be here?”

Of course, I currently had no idea whether or not I would be attending the next party, which Mom’s kitchen calendar had told me was scheduled for 5/4. Depending on what happened in the next four weeks, I might be gatecrashing it, I might be a bona fide guest, or I might be on the bottom of either the Sudbury or Cambridge reservoirs, in a bag weighed down with two of Dad’s old bowling balls. I’m normally an optimist, so I went with the idea that I’d still be around, and still be intact with a working penis and two testicles. I smiled and looked her at her eyes behind the mask.

“It’s a date!”

“Yaaay!”

After I’d soundly kissed both the girls again, and they’d frenched each other to celebrate, we quickly washed up in the bathroom. It was time to join the rest of the party.

Another kiss all round, and we headed downstairs to see what was going on; but we didn’t get as far as the Great Room.

There was a group of three latecomers down in the hall, an older couple and a skinny younger guy, about our age. They had already stripped naked and put on their masks and wristbands. The lady smiled as she asked me to look at their test certificates. Yeah, they were all in order, but she hadn’t folded the papers to hide the personal information, so I could see that they shared a surname and address. It looked like we had a father & son, and a mom. I whispered that information to Jessie while they were finishing putting their boxes against the wall, and she invited them to join us upstairs. The boy was already stiffly erect from gazing at two naked girls, and I just hoped he was man enough for them. At least at our age his recovery time would be very short. Laura took the older guy up first, followed by Jessie with the boy, but the mom seemed a bit hesitant to go after them.

I took her hand as we lagged behind. Sis and Jessie vanished into her bedroom, and I looked at my new partner. She seemed embarrassed. Knowing she had arrived with husband and son, I took an informed guess at the cause.

“Would you rather we used another room?”

My companion smiled gratefully, happy that I had understood her hesitation.

“I’m not yet used to having sex with someone while my son is with a girl on the same bed!”

“You don’t look old enough to have an adult son!”

She jokingly smacked my butt.

“Flatterer!”

“MILF!”

She gurgled in amusement. It was a lovely laugh. Although I guessed she was slightly older than Mom, probably in her mid-forties, she was in great trim, and I reckoned that I was in for some more fun.

I’d never considered dating older women; now that Mom had unknowingly put them in my way, I was an instant convert. The two I’d fucked last time had been most enthusiastic; there was no doubt in their minds that they were there for great sex, and there was an eagerness and open-ness that I had never found with a high-school or college girl. Even Amy had normally demanded a ‘date’ (which somehow always involved me spending my money on her) before we went back to her room for sex, and I’d never been entirely sure that I would be invited back until the moment came. This lady, like the other two, was raring to go.

Her pink wristband was number 21; I remembered that her husband had been number 19. So there were slightly more people around tonight than last time, and a much closer match in males and females. I led her into my own bedroom, and again closed the door for privacy. The last thing I wanted was a spectator, especially anyone who might know me.

She had a very neatly trimmed little landing strip in reddy-gold, which matched her head hair. Apart from a tiny paunch from child-bearing, her belly was flat and her figure showed that she worked out regularly. Her tits were slightly larger than either Laura’s or Jessie’s, but didn’t sag, and when I had got her laying on her back on the bed, her nipples were just as responsive to my tongue and lips. I reckoned that I could be in for a good time.

She was by no means the first female I’d had naked in my bedroom, but things were now very different from the times I’d brought a high school date up here.

(That had been the one advantage of the Friday nights of my Senior year when my sister, if she was back home from college, nearly always had a date and my parents were also out at yet another dinner party; I did have a place where I could bring a girl back to make out on our own in the house, and most always I’d gotten lucky as well – the prospect of being able to get totally naked on a real bed behind a locked bedroom door, rather than partly clothed on the back seat of the car parked up somewhere, had generally tipped the balance between me merely playing stinky finger and getting blown, and getting my dick wet. I’d even used all three condoms in the pack on several occasions, and that had never happened in the car.)

As I worked my way down her body, I noticed a couple of very small scars on her belly. I kissed them and she giggled.

“What are they?”

“I had my tubes tied a few years back. Pretty neat job, hey? It used to be a ‘cut you open’ job, but with laparoscopy, it’s real simple these days.”

“So it won’t matter if I cum inside you?”

“I’d be very upset if you didn’t! The man pulling out always ruins the moment!”

“I’m very glad that we don’t have to use condoms; I so much prefer lying together for a few minutes afterwards. Kinda makes it more affectionate, rather than having to leave right away in case the condom falls off!”

She grinned.

“Me too! It’s always better to do that. I hate it whenever the man just grunts and rolls off, but the guys here are all better than that, well, most of them. There are a couple I wouldn’t go with again.”

I stopped talking and started muff munching.

I did some thinking as well. I decided that I was glad that we were in another room from the girls; although part of me wanted to experience fucking someone with Jessie and Laura being fucked beside us, I didn’t think that I was ready to witness the two gorgeous pussies that I’d lovingly prepared and attended to for the past hour, just being pounded by two random guys. I reckoned that there wouldn’t be much in the way of foreplay; because the girls were already wet and willing, they’d most probably just stick their dicks in and get on with it. The young guy had probably shot already; but I knew Jessie had the skills to get him up again very quickly so that she would get her cum.

Meanwhile, I was enjoying myself making her labia grow pink and puffy, with the odd little foray to persuade her clit to reveal itself. From the little moans and gasps I could hear, she was beginning to get into it too. It still took a few minutes for her natural lubrication to start appearing. I gave her a very nice little starter orgasm, and then used my finger on her G-spot and my lips on her clitty to give her one a bit further up the Richter scale. Then I moved back up, via her crinkly nipples, and kissed her on the mouth. She put an arm around my neck and kissed me right back.

I was in no hurry. I’d already cum twice, in my sister and her roomie, and the night had hours to go yet. This lady was indeed a lot of fun, and I was happy to take my time and give her as much pleasure as I could. I liked her humor, and I liked her attitude.

“Any preference?”

She smiled. I wondered what she’d look like without the mask; she had a great smile, and I could see the twinkle in her eyes through the eyeholes, even if I couldn’t see her full expression.

“I’ll start off on top, please!”

I reached for the lubricant which our hosts had thoughtfully provided on a tray on my bedside cabinet, and applied a coating to my cock. My partner was more than wet enough at her opening, but if she was going to try to get me balls deep, a little bit of artificial assistance never hurt. Besides, I’d learned from the previous party that prolonged screwing caused wear on my dick, and I wanted to minimize that.

She started cautiously; she was fairly tight to start with despite our foreplay, and she sat on me for a few minutes while she settled down around me. I enjoyed myself caressing those babies of hers, and she didn’t try and stop me. She did a bit of experimental rocking, and smiled at the results.

“I’m ready now, so hang on for the ride!”

I put one finger up across her lips.

“There’s absolutely no hurry; I’m yours as long as you want me. Take it slowly and let your orgasm build how you really like it.”

She nodded, and as I let my finger drop, she dipped forward and kissed me on the lips.

“Thank you, I really appreciate that.”

I returned to rubbing my thumbs over her erect nipples; she hissed as her synapses simultaneously got the messages from there and her clitty rubbing on my pubic bone.

She took me at my word. She placed her hands palm down on my chest, and slowly rocked herself on my cock, making soft mewling sounds of contentment as she got into the rhythm that best suited her.

“Oh, yes, that’s really good!”

She bent down to kiss me on the lips, and then shifted her position slightly so that she could use her thighs to lift up and down on me. I flexed my knees so that I could push my hips up as she came down, and she gasped as I started my movement in concert with hers.

“Oh lord! That is soooooooo goooooood!”

I moved my hands to her waist to help her; she was driving up and down almost the full length of my dick, and although it felt wonderful to me, I knew that I wasn’t going to shoot anytime soon. It clearly felt pretty darn good to her too, because a few minutes later she keened out a serious climax and froze in position for a moment before sinking down onto my chest. She lay there for a bit, getting her breathing back more regular, and then she kissed me.

“Did you cum too?”