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Man Smart, Woman Smarter!

After a fun visit to California last year to check out colleges, my wife’s little s****r Cindy did end up enrolling at UCLA and moved into our back bedroom since the cost of renting in Westwood is prohibitive. Plus, she needed some help adjusting to the casual style here in southern California. Well, I thought she needed help anyway.

Cindy went through sorority rush in the fall and joined a popular group of girls on campus. I assumed the pretty redhead was well on her way to a busy social life and I was happy for her but still, still I have to admit I was smitten with her and always had to fight off jealousy, especially when Melissa described her little s****r’s sexual escapades. My wife knows how much I admire her s****r and she likes to bring up her adventures when we have sex…just to spice things up I guess.

Well, all she was doing was driving me crazy with desire for her unspoiled little sibling as she related various incidents in which Cindy barely managed to hang onto her virginity!

One night a car pulled up outside our suburban house and I saw Cindy climb out of the passenger door, yell a few choice comments at the guy behind the wheel and then slam the door. By then Melissa was awake and wondering what was going on. She went downstairs to speak to Cindy and she was gone quite a while. When she finally returned she shook her head as she settled into bed next to me.

“Another tough night for our little boarder.” She said in resignation. “My s****r just seems to end up dating the wrong kind of guys.”

“What do you mean honey?” I asked. “Look, we both know she has to lose her virginity sometime. This is Los Angeles in the two thousands. Guys expect more than a sweet goodnight kiss.”

“I know, I know.” Melissa admitted. “But Cindy just isn’t ready to jump into bed with the first knucklehead that comes along with a stiff dick.”

“Unlike her older s****r!” I couldn’t help but shoot back.

“Actually you weren’t the first, second or third knucklehead!” She teased back, “In fact…”

“Okay okay.” I caved in. I really didn’t want to go there. I’m well aware of the “Experience” that my wife had when I met her. There wasn’t much I was going to be teaching her about cock, believe me!

“Well, what happened tonight to provoke all that door slamming.”

“Well, she has been seeing a fellow, a Sigma Chi, and she’s been sizing him up and is, you know, interested but not ready to fuck somebody in the back room of a crowded fraternity house where anyone can and will walk in at any moment. She’s a young woman now and she’s allowed to take her time. So I guess Andy feels three dates with kissing and petting is enough ‘foreplay’ and he got pissed off at her when she wouldn’t let him take off her panties.”

A secret smile came over me and I was glad it was dark in our bedroom. “Atta girl Cindy!” I thought to myself. I know, I know, it’s insane but I couldn’t help but dream that one day I would be the man taking off those little panties.

“An argument ensued and Andy told her he wanted head. Well, Cindy has never done that and attempted to fish Andy’s cock out of his pants intending to give him a hand job, which I guess she’s done before. My little s****r thinks sucking cock is ‘gross’ and doesn’t want ‘slime’ gushing into her mouth. Anyway, Andy rudely told her she can’t even give a decent hand job and maybe she needs to go the fuck back to Iowa or wherever she came from.” Melissa sighed in sympathy with her little s****r.

“Melissa, nowadays cock sucking is considered part of any real sexual relationship.” I offered. “You know men want it and she’ll have to do it some day. I don’t think he’s really asking for…”

“Jeff, it’s the way he asked that pissed her off.” Melissa told me firmly. And I knew she was right. I found myself wondering what Cindy had done wrong while jerking this guy off. We both knew she’d had some experience with hand jobs back home. “None of my business.” I decided. There are things a young girl like Cindy has to figure out for herself.

I assumed my wife would have a chat with her little s****r in the morning and I was right about that. Knowing she now had the scoop I had to gingerly bring up the subject. I was musing about how to accomplish this when Melissa sidled up to me and suggested we have a nice f****y barbeque tonight. “You know, some wings, slaw, maybe some fries and a nice bottle of that Cabernet that Cindy liked last time.”

Hmmm. This sounds like maybe there’s some plan afoot but, as usual, I’ll be the last to know what it is. But, I knew Cindy was apparently part of this plan. And that was fine with me!

“Okay Melis'” I told her, “I’ll go hit Trader Joe’s right now.”

I got the usual stuff for a barbeque dinner. I’m no Wolfgang Puck but barbeque I can pull off. We had the satellite radio playing out on the patio and the weather was cooperating too. A lovely evening. I couldn’t help but gaze longingly at Cindy. She wore her red hair with a casual part in the front but cascading down onto her shoulders. She had these dark hazel eyes and perfect pink lips. She was wearing little pearl earrings and always seemed to have a slight smile on her face.

That night, out by the pool, Melissa’s little s****r seemed to get more and more beautiful as the light began to fade. She was sitting across from me and still sipping on that Cabernet. Cindy was wearing a little white top and a fairly short powder blue…Bruin blue, I guess, skirt. From time to time she shifted her position on the lawn chair and I was treated to a brief glimpse of her white panties. Yes, I snuck into Cindy’s room from time to time to check out her panty drawer. She had a few racy Victoria’s secret panties that were lavender or pink but mostly virgin white bikini panties, which suited her in my opinion.

So, yeah. I was getting buzzed from the wine too. Melissa and I like a toke or two before going to bed which seems to enhance our sexual fun. Also loosened up her tongue! It was usually after that toke that Melissa would willingly tell me of her s****r’s exploits.

So, I wasn’t shocked when she produced the bong and commented that Cindy had already noticed it stashed in the garage and admitted that everyone did bong loads at the frat parties she regularly attended. So, the three of us each got a lungful of potent herb and we settled back to feel the effects coming on.

Cindy soon began to giggle which her s****r also does when high. I wondered what Cindy was giggling about. I looked at Melissa and she was kind of nodding her head yes.

But Cindy just giggled, as if she had something to say but just couldn’t say it. Eventually Melissa broke the ice.

“Jeff, my s****r wanted to talk to you about something but she’s too embarrassed to say it directly.”

“Well, I’m mellow!” I blurted out, trying to suppress a cough. That was some strong weed! “I don’t think there’s anything that would shock me right about now.”

Still, Cindy giggled and Melissa helped her little s****r out with this ‘secret’ topic she wanted to bring up.

“Cindy says she’s not quite ready to have sex for the first time but the fraternity boys, after a few dates, expect sex from a girl. There’s a guy she kind of likes but he says she doesn’t even know how to give a decent hand job. He really wants oral sex but she doesn’t think she would like something like that.”

I just nodded my head, closed my eyes for a moment and then opened them awaiting the rest of her narration.

“Well, I told my little s****r that you and I both enjoy a nice hand job and you’ve gone to great lengths to educate me in that particular fetish.” She gave me a knowing wink when she said it.

“It’s not really a fetish,” I objected, “I mean, it’s just a way of providing some variety in your sex life. After you’ve been married for a while…”

“Jeff, I didn’t mean it was kinky or anything. I just meant that, well, the way you like it is a lot more involved than just sliding and jerking. Wouldn’t you agree?”

She had me there. Besides, I wasn’t close to objecting to what I hoped the s****rs were proposing.

“I…I do like a nice hand job.” I playfully admitted. “And, yeah. If both parties are really trying to please the other, it can be very satisfying. VERY satisfying!” I lifted my eyes towards heaven when I said it.

Now both s****rs were giggling and then, again, Melissa took the initiative.

“Okay Jeff, I think maybe if my s****r were to spend a little time with you…upstairs while I’m doing the dishes, she could pick up a few pointers about how to go about pleasing a man with her soft little hands. You know, keep him interested until she decides…”

I chuckled and then interrupted: “Yeah, until she decides when and where! She’s the girl and the girl gets to make the rules!” All three of us giggled at that point. I told the girls I was a bit sweaty from 18 holes that afternoon and I wanted to wash off some barbeque smoke I’d acquired. “I’ll hit the shower and we can take it from there.”

Melissa gave me a sly smile and said: “And don’t have too much fun you guys!”

I was almost trembling as I made my way upstairs and into the shower. I shaved my whiskers and lathered up anywhere and everywhere, my mind spinning. Wow! Me and Cindy! Of course it was just a hand job but, instead of my wife stroking me and describing her little s****r, it would be me and Cindy! I toweled off and put on my robe before exiting the bathroom, not sure what to expect in the adjacent bedroom.

The lights were dim but, when my eyes adjusted, I saw Cindy there under the covers. Waiting for me.

And believe it or not, I started to get cold feet! Gee, was this what I really wanted to do? I truly did love Melissa and always appreciated how sexually adventurous she was. Was this something we would both regret? I mean, we couldn’t take a sexual encounter…even a hand job, we couldn’t take that back you know?

So, it was with a bit of hesitation that I sat down on the bed and looked down at my little s****r in law. As usual, she wore that half smile and her beautiful hazel eyes were shining up at me. It was almost like she had somehow already managed to get past the trepidation that I was experiencing. She seemed to recognize that unsure look on my face.

“Jeff, if you want, you can just tell me about how you and Melissa do it. I don’t want to, you know, get you into any kind of, you know, make any trouble between you and my s****r.” She said softly. Remember that old song that Lucy and Ricky sang on the “I Love Lucy” show? “Man smart, Woman smarter?” Here was my little virgin 18 year old s****r in law trying to make it easy on me. Right about then, I realized I had nothing to fear from this encounter.

“I’ll tell you what.” I began, “If either of us thinks we’re heading for trouble, we can call if off…but I don’t think that’l happen!” I said smiling down at her. Cindy looked so beautiful lying there under the covers. I dropped my robe and climbed under the covers naked and reached for her.

“Well Cind’ we usually start with a kiss!” I nodded my head at her and she closed her eyes and pursed her lips up at me. And it started out small…just a little smooching and nibbling but then it progressed until we were ferociously going at it. It was like all of the pent up desire I had for this gorgeous young creature came to the surface. She sucked softly on my tongue as I held her to me, feeling her tight little tits poking me in the chest. I reached down and was thrilled to feel that she hadn’t shed her panties!

“Mmmmm!” I moaned. “What color are your panties Cindy?” I mused.

“They’re white Jeff. Your favorite. I’m wearing white panties for you!” I gave an involuntary grunt and quickly reached for her skimpy underpants. Oh, they were soft and smooth and, just beneath, her virgin pussy awaited me!

More kissing ensued and then I felt it was time for Cindy to lube me up. I grabbed the Astroglide from the nightstand and told Cindy to get me all slippery and to use both hands.

She was a quick learner and easily had me hardening in her soft, well lubricated hands.

“Use both hands honey, and not too hard at first.” I advised. “Now, usually, Melissa will come up with some kind of fantasy story about an old boyfriend or her first time doing anal or…”

“Or her little s****r?” Cindy interjected. “Her little s****r’s pussy shaving experiments?”

I realized maybe the s****rs had shared more information than I thought. I was at a loss for words. I knew then that Cindy understood my sexual fascination for her. I was quiet for a few moments. Then, as if she understood what I was feeling, Cindy spoke.

“What about you Jeff?” She began, “Maybe you could describe your first time to me and, you know, get me excited too!”

I wasn’t prepared for that but Cindy just kissed me again and again and continued stroking my now rock hard cock until I collected my thoughts.

“I had girlfriends in high school but I always seemed to pick ‘nice girls’ who would never consider going ‘all the way.’ This led to a lot of sexual frustration. Then, I met Darlene. We were in photography class together and the next thing I knew I’d asked her out to our school football game the upcoming Friday night. Well, we had fun cheering our team on and later we stopped at A&W for burgers and root beer. Darlene had moved over right next to me on the bench seat of my Dad’s Impala and her body felt nice and warm there touching me.”

Cindy moved right next to me in the bed and did a good job of snuggling up to me as she continued to fondle my balls with one hand while stroking me slowly with the other. “Did you kiss her Jeff?”

“I did steal a kiss while we were waiting for our food and Darlene really seemed to like that! Well, afterwards I was driving her home assuming our evening was over. When we got to her street I went to make a right but Darlene grabbed the wheel and, smiling all the while, sent me a message: ‘I don’t want to go home just yet.’ Knucklehead that I am, it took me a few moments to figure out what Darlene wanted to do instead of ending our date. I slowly drove up Zelzah to the hills overlooking the Valley. We were going to park! Darlene was hanging onto my neck now as I found a scenic spot and parked the Chevy. And then, then we went at it! Loads of kisses and then, for my first time, French kisses! Darlene gave up waiting and just stuck her tongue into my mouth and wagged it all around which delighted me. Right about then, I began to steal my hand down to Darlene’s knee and, encountering no resistance, I began to slide it up her leg, kissing her all the while as if to distract her. But Darlene didn’t really need much in the way of distraction! No, she kept kissing and frenching me until, at last, I touched her panties!

“You touched her panties Jeff? Could you feel her pussy right beneath them” Cindy wondered. Then, Cindy removed her hand from my cock shaft and took it down to her crotch…right onto her panties! I thrilled to my first ever touch of My wife’s little s****r’s hot little white panties and gasped as she opened her legs to give me better access!

“Yeah, I could barely feel the division she had down there…under her little cotton panties. Then Darlene quietly spoke…”Jeff, don’t take off my panties! I’m a nice girl Jeff. Don’t treat me like I’m just a little toy or something.”

“I…I know Darlene.” I managed to stammer back. I waited a moment to try to figure out what to do next and then muttered “I won’t take your panties off, but, may I feel your panties? Just for a minute and then we can go home.”

“Darlene didn’t say yes or no but she didn’t object as I continued to fondle her soft white panties. I really didn’t know much back then but I was trying to please her. Then, I heard her moan. A moan of pleasure to be sure. I realized I was doing something that was apparently feeling really good to her. And so, I kept it up. I felt up Darlene’s barely covered pussy while she held her legs open for me. But, now I needed something too. I didn’t know what to say but, again Darlene, who seemed to have a lot more experience than me, took the initiative. She reached over and attempted to pull down my zipper. The tight slacks I wore back then made that difficult and, eventually, I just went ahead and undid the zipper and my belt which freed my frustrated cock!”

Cindy renewed her assault on my well lubricated cock, stroking me firmly and softly fondling my balls as she waited to hear more salacious details!
“Darlene’s eyes widened when she finally got to see my bloated hard on. She seemed to really like what she saw! A strange look came over her face right about then. She was no longer smiling. It was as if she couldn’t help what she was about to do.”

“Forgive me Jeff.” Was all she said, and then she said it again, “Forgive me for what I’m about to do.” With no further words, Darlene leaned down until her head was right in my lap. I never got a chance to think about it, it happened so quickly. Suddenly, her warm and wet mouth was all over my turgid cock! I impulsively stuck my cock upwards and it slid salaciously into Darlene’s hot sucking mouth! I just followed my instincts and continued to shove as much cock as I could right into Darlene’s mouth while she whimpered submissively there in my lap. I knew I couldn’t last long and I really didn’t want to either!”

“Did you…did you get to fuck her Jeff?” Cindy inquired. “Did you get to fuck her or did you come in her mouth?”

Now I was kissing Cindy again and again and I secretly slipped my hand under the legband of her panties and, for the first time ever, I touched Cindy’s bare pussy! It was good and slippery too as you might imagine. She’d become excited as she listened to my narrative. Now, this wasn’t how Melissa and I did it at all but, my god! It was exciting! I teased the soft pink lips of Cindy’s pussy as I told her the rest of my “First time” story.

“I wanted to fuck her Cindy! Oh my god I wanted to but Darlene kept sucking and then she tightened her lips and sucked even harder! I was moving my cock in and out of her mouth and she was moaning and whimpering and then…then I was there and it was too late! I called out her name and began to ejaculate, right into her hot sucking mouth! I experienced such pleasure It’s impossible to describe. Just jolt after jolt of excitement as I helplessly filled her mouth with my sperm. Then, it was over.”

“Did she swallow all of your come Jeff?” Cindy wanted to know.

“I really don’t know honey. I’ve thought about that many times over the years but I’m not sure what happened. I know My Dad didn’t yell at me about a stain on the seat cover or anything. I know there was a lot, but where it went I’m not sure.

I began to attempt to penetrate Cindy’s tight little virgin hole but it seemed impossible so I resumed lightly stroking her sweet young pussy lips.

“I guess it’s your turn now Cindy,” I whispered into her ear.

“But, Jeff…I don’t…I don’t have a first time yet!” She admitted. “I mean, I fooled around a little back home but.”

The pretty redhead seemed to be lost in her thoughts for a few moments but then she spoke quietly.

“Jeff, would you like to…to look at me?” It was awkward but at least she’d said it. I smiled and nodded my head as if to say “You Bet!”

Cindy slowly pulled the covers from her breasts and gave me an up close and personal look at her wonderful little tits! No, not big at all but so pretty and pink and soft and those nice gumdrop nipples up on the crown. She was so exciting to look at right up close. Then…then she continued to move the covers down until all she had covering her pussy was her little white bikini panties.

“Should I…should I take my panties off for you Jeff?”

“Oh, not just yet Cindy.” I smiled. By now, Cindy knew how much I loved her panties and I loved some teasing too. Catching my drift, the pretty teen then opened her legs well apart and took the legband of her panties in her fingers and slowly pulled it to one side, completely exposing her sweet young pussy to my excited gaze! My goodness! Look at that! Not at all like her older s****r, Cindy had just the tightest little pink slit with her little tuft of hair just above it! I found the pale pink skin of her pussy lips to be wildly exciting and I began to stroke my still well lubricated cock as I drank in the lurid sight she was presenting me with!

“Wait, Jeff. There’s something else I think you might want to see!” She said playfully. With that, Cindy scrambled onto her hands and knees and looked back with a smile, knowing about all the power she had in her incredible ass! “Go ahead Jeff…” She told me, “Go ahead and pull down my panties so you can see all I have!”

She was calling the shots now and I was helpless to do anything but comply with her request. I reached for the waistband of her panties and slowly pulled them down, exposing first her asshole and then the tightly closed lips of her pussy! My wife’s little s****r then lowered her tits to the mattress causing all of her rear charms to open even more for my inspection! But I wanted to do more than just look. No, I wanted to get real up close and personal with Cindy. This might be my only chance and she figured to be in my life for a long while. Funny the things you think about when you find yourself in this miraculous situation: Your wife’s virgin s****r is kneeling before you, her little white panties hanging helplessly from her thighs and her tiny dimple of an asshole and tightly closed pussy beckoning to you. As if to say “Come closer…kiss me!”

And so I did. I moved right up behind Cindy and kissed her tight little asshole and then her never before touched young pussy! She was young and sweet and well lubricated. Yeah, it was supposed to be a hand job and nothing more but I was now fighting a losing battle with my conscience. I took my rigid cock and moved it right up into the groove of Cindy’s sensuous butt cheeks and then began to rock to and fro…sliding my overstimulated prick all over her pussy lips and asshole! I heard her moaning and knew she was excited. Cindy began to move back to meet my uncontrollable thrusts. She was watching my eyes now. The look on her face said “Go ahead Jeff…please go ahead…”

But I hesitated. Was this the right thing to do? Really? I was more sexually excited than I’d ever been by this incredibly hot young woman but…but…

“Oh Jeff, Fuck Me!” Cindy finally begged. She made the decision for me and I realized sometimes a man has to take what he needs in this situation: Take what he wants so badly…just because he can. I jerked my cock right to the quick of my little s****r in law, right to the entrance to her virgin pussy and then began to push it in.

“Nnnngh…” was all Cindy could muster as she felt her first sexual penetration taking place. I know, I know, I should go slow and be gentle but I just wanted that sweet young girl so bad I just grabbed hold of her waist to hold her in place and then pushed hard and managed to hilt myself to the balls in her incredibly tight young pussy! I was plenty lubricated and, when I’d achieved complete penetration, I gave her a few moments to try and adjust but then I began to fuck little Cindy and fuck her good! Sweet strokes. Over and over, and right into her no longer virgin pussy. I rubbed her tight asshole with my finger and she cooed when she felt that sensation. The sound of my balls slapping into her pussy lips filled the bedroom. Then, after a couple of minutes, Cindy began to moan in pleasure and move back to meet me as I buried every inch of my big hard cock in her pussy. And then the two of us were moving together like lifelong lovers…thrilling to each and every stroke. I wish I could say I lasted for a half hour but the over the top sexuality of this unexpected encounter was too much for that and soon…sooner than I wanted, I felt my sperm beginning to rise and I quickly pulled my cock from Cindy’s disappointed young cunt. With a deeply satisfied sigh, I sent squirt after squirt of hot gism all over Cindys virgin asshole. It slowly drizzled down and coated her pussy lips.

We collapsed together, as lovers do in such a situation, and our lips met. We enjoyed one last deep soul kiss before we realized that this had to be our last time together. I wish I could’ve had both s****rs. I really do, but that wasn’t to be. And after all, Cindy had her own life to live and destiny to meet. And so, we both returned to the shower and cleaned up before heading downstairs.

Melissa was long finished with the dishes when we finally made it downstairs. I wondered exactly what the s****rs had planned. Was this really supposed to be “Just a handjob” or did Cindy ask her s****r if she could lose her virginity to me. My wife has never asked me what transpired in my brief interlude with her s****r. I can’t imagine I’ll ever ask either of them and, consequently, I doubt I’ll ever know. It’s like I said earlier: Man Smart, Woman smarter.

Updated: October 21, 2016 — 1:30 pm

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