Wife, Best Friend . . . And Sister

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Finding love with my little sister.
24.6k words
4.6
192.4k
273

Part 1 of the 2 part series

Updated 06/07/2023
Created 08/12/2015
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SmallTitFan
SmallTitFan
1,969 Followers

Life hasn't been too good, lately. I got "divorced" about six months ago. Actually, we weren't married, but we had lived together for a few years and it felt like we had been married. Since the breakup, I've done some of that online dating and had a number of first dates but I haven't meet anybody that really got me excited. There were a few nice women in the group but none of them really commanded my attention.

To understand the predicament I'm in, you need to know some of the history. I've been married two times. The first time I was only 23 years old. Of course, back then, I knew more than anybody else in the whole world. I knew exactly what I wanted - or so I thought - and I thought I had her: pretty blonde girl with ample cleavage, pleasant to be with, and not particularly a dizzy blonde. The first two years, everything was great and the sex was fantastic. Unfortunately, she got bored with me and moved on without actually moving on. When I discovered that I had been replaced, I divorced the bitch (thereby confirming the truth to that expression: "for every good looking girl walking down the street, there's a guy somewhere who got tired of fucking her.")

The second marriage was a rebound marriage. The first divorce wasn't my fault, "of course," and I wanted to prove that I was not the problem. I was perfectly capable of having a satisfying and lasting relationship with a woman; just give me a woman and I would prove it. Unfortunately, I did what so many people do and I went and found a woman just like the last one: pretty blonde girl with ample cleavage, pleasant to be with, and not particularly a dizzy blonde. Again, the sex was good for a few years but then she started talking about having kids and I really didn't think I was ready for that. When I said "no way," she said "no more," and she filed for divorce. It was probably a mistake on my part but you can't un-ring a bell.

I realized that I never really missed my first wife but I missed the second one in a bad way. After some very serious thought on the subject, intermingled amongst frequent encounters with thought-inhibiting Cuba Libres, I realized that what I really missed was the sex with number two. She wasn't "freaky" but she was uninhibited; she was very, very uninhibited. She swallowed. She sometimes massaged my prostate while she made me cum with her mouth. She gave me rim jobs. We did 69 all the time. She loved to have me eat her pussy while I fucked her ass with a vibrator. She loved to have me fuck her ass while she fucked her pussy with a vibrator. She loved for me to lick whipped cream out of her ass crack. I couldn't think of any way that two people could have sex that we had not tried. And . . . she wanted sex all the time, not just once or twice a week. If I had stayed with her much longer, she probably would have fucked me to death . . . and most happily would I have gone to my grave.

Anyway, after two failed marriages, I decided that maybe I should hold off on any more thoughts about matrimony. You know, you shouldn't get married just to have sex. I've had lots of sex as a single guy and, besides, some people just aren't suited for marriage. Who know, maybe I was one of them. And, if I didn't want to have kids, what was the point in getting married, anyway?

I decided to start dating and I gave it everything I had. I met so many women I can't remember all of them and I had a number of flings that were filled with casual sex that ranged between mediocre (which means "good") and great. I was happy and I thought that the women I dated were also happy but, eventually, it felt like something was missing.

I was about 34 years old when I had that realization. This required discussion with a most trusted member of the opposite sex. I called Lynn and suggested that we meet for dinner that Friday night. She had really, truly been my most trusted confidant and we had been best friends since forever. She was two years younger than me and had been divorced for 4 years after a relatively brief marriage to Gary that did not produce any children.

We met at one of the many wonderful restaurants in St. Augustine. "So what's wrong with the stud's life?" she said a bit sarcastically as we were being seated at our favorite Italian restaurant.

"What's with the attitude?" I responded.

"Well, Jack, you have this series of meaningless encounters with bimbos who are eager to suck and swallow and probably even do the back door stuff that I've only read about in Cosmo and you obviously get more sex than you can possibly handle and now you're wondering why your life is meaningless while I haven't gotten laid since I left Gary and I'm wondering why life seems to be meaningless. Aren't you smart enough to figure it out?" she asked.

"Why do you think all I have is meaningless encounters?" I retorted.

"Okay. The last three girls you dated - was it Linda, Millie, and Susan? - tell me where they were born. Or their father's first names. Or what their dreams were. Can you?"

"Well, uh . . .." was the most intelligent response I could formulate.

"Listen, maybe I shouldn't be so rough on you. Part of me is jealous. Do you realize how long it's been since I had sex? The last time I did it, Eisenhower was the president, that's how long!" she falsely declared. We both laughed.

"No, I didn't know," I responded, "except that you just told me you hadn't gotten laid since you left Gary, so . . . I guess I should offer my condolences."

"Well, if I had gotten laid, I would have told you. It's not that I don't get any offers, but . . . you know what they call a girl who has sex with as many different people as what you've had? Slut, whore, easy, tramp, cum bucket . . . you get the idea. So I don't jump into bed with a guy on the first date and most of those losers decide to not invest in a second date since they didn't get to fuck me on the first date."

"Have you considered," I began tentatively, "buying one of those battery operated things?" It was my turn to laugh and Lynn quickly joined in.

"For your information, some girls are raised differently than guys. Maybe those sluts you hang with are different, but good girls are told to save ourselves for marriage, that touching ourselves is wrong, that only low born, ignorant gutter sluts own sex toys, and . . . we proper ladies end up being a bit more inhibited than you guys, so . . . no, I haven't considered it."

"I guess my problems don't seem very significant compared to yours," I meekly admitted.

"It doesn't matter how many problems other people have. If you've got a problem . . . you've got a problem. And right now, I would say I've got a problem and you've got a problem."

"Got any suggestions?" I asked.

"I need to get laid and you need to meet someone you can settle down with for a long term relationship but none of that's gonna happen tonight, so . . . let's just go back to your place and get drunk."

"Damned good idea!" I eagerly agreed.

We finished dinner and drove back to my apartment. We decide to watch a movie and drink margaritas. We sat on opposite end of the sofa and watched what I initially believed was a bad movie. It was about a Mexican brother and sister who are kidnapped and forced to have sex while their kidnappers video the encounter for later blackmail use against the father. The plot was thin and the action was slow and I was about to change the channel when they got to the big forced sex scene between the brother and sister and suddenly it got pretty damned hot.

As soon as the big sex scene was finished, Lynn started acting sleepy and she turned so that her back was against the arm of the sofa and her legs were up on the sofa cushions. Initially, her legs were lying flat on the cushions but after her fourth margarita, Lynn had pulled her feet back towards her so that her knees were raised up. She was wearing a skirt but her legs were together and she was not revealing herself in any way.

As the movie slowed down and the alcohol kicked in, Lynn was getting more and more drowsy. As she started to doze off, her right leg crept over to lie against the sofa back and her left leg dropped to lie on the seat cushion. She was essentially in a kicking frog position and it had the effect of exposing her panties to me.

Making sure that her eyes were really closed, I looked down at her panties. They were white and very lacy, very feminine, and . . . one other thing . . . I saw the outline of her pussy lips and I thought I saw a wet spot towards the bottom of her slit. I knew I shouldn't be taking advantage of the situation by looking but . . . I'm a guy and I couldn't help myself.

I remember briefly fantasizing about Lynn being so intoxicated that I could remove her panties without her waking. I knew that would be the wrong thing to do, but I really wanted to see her pussy. Her cunt lips were so pronounced that I assumed that she shaved her pubes and, she was such a sweet girl, I just assumed that her pussy would smell - and taste - just as sweet as honey.

I got off the sofa and knelt beside her. "Sweetie, you're passing out. You can't drive home tonight so you just need to stay here. Let's get you into my bed and I'll sleep on the sofa tonight."

"Huh?" she muttered as she opened her eyes. After a few seconds, she noticed the position of her legs. "Not the most ladylike position for a conversation with a gentleman," she laughed. "I hope you enjoyed the show!"

"Well," I began my confession, "I've always thought you were a very sexy lady and, yes, I enjoyed the show but . . . don't worry, I didn't take pictures and I won't tell anyone."

"What a gentleman you are!" she insisted in a rather tipsy tongue-in-cheek manner.

"Indeed!" I agreed. "Do you need help getting up the stairs?"

"No, I'll be fine," she said, but her attempt to stand immediately proved the falsity of her statement.

"Okay, let's try something different," I said as I picked her up in my arms like a groom gathering up his bride for her first trip across the threshold.

She looked up at me and batted her eyelashes. "You're my hero!" she declared with feigned adoration.

"You can be so damn silly sometimes," I responded. As I got to the top of the stairs, I asked, "Do you need to make a pit stop?"

"Uh huh," she responded affirmatively.

I carried her through the master bedroom and into the bathroom and then deposited her atop the vanity.

"Thanks for taking care of me," she said. "You're the best!"

"You deserve the best," I replied. "I assume you can take care of yourself in here, so I'll be waiting in the bedroom."

I waited a few minutes and started calling her name but got no response. I gingerly approached the bathroom door and eventually looked in to see Lynn passed out on the toilet. She had taken off her skirt and blouse and her panties were down around her ankles. She had unfastened her bra but it still loosely hung around her shoulders enough to conceal her little boobs.

"Lynn!" I called again, but I got no response.

I assumed that I would need to put her to bed. I didn't want to take any liberties with a passed out girl - although I was tempted - but, since she had taken a female leak, I needed to wipe her and then I needed to remove her bra so that she wouldn't get tangled up during her sleep.

I got some tissue and pushed her legs apart. As I suspected, her pussy was very clean shaven and, if this was some bimbo that I had just brought home from the bar, I would have climbed on and fucked that pussy until she woke up and begged for mercy. However, none of that would happen tonight.

I pulled her panties up as high as I could get them while she was still seated and then I picked her up and carried her to my bed. As soon as she was on the bed, I finished pulling up her panties and I pulled the bra away from her boobs and dropped it on the floor.

Lynn's boobs were the most perfect boobs I had ever seen. They were small, probably not more than a 34B, but they were perfectly proportioned for her petite body and the skin was perfectly smooth and free of any blemishes or imperfections. Her areolae were small - only about the size of a quarter - and her nipples were hard, I assumed, from exposure to the cool air. They looked oh-so-suckable. If this was any other girl . . .. The temptation wasn't just that she was so stunningly beautiful that no mere mortal could resist; the temptation was that I knew her so well and, in addition to being very attractive, she was a sweet, charming, interesting, accommodating, delightful lady. If only I had a girlfriend like this, I thought. If she had been awake and made that "come hither" sign with her index finger, I would have jumped in bed in an instant and been delighted to do so. However, taking advantage of a girl who is intoxicated and passed out is rape, pure and simple, and I would never allow myself to succumb to any such temptation, especially with my sister.

I covered Lynn with a sheet and light blanket and left a night light on in case she woke up during the night. I went downstairs before I began to have any other notions about what I should do to her almost naked body, and I made a stop in the downstairs restroom. After my exposure to that amount of temptation, I needed to relieve myself or I suspected that I would never get to sleep.

* * *

The next morning, I awoke with a slight hangover. I downed some ibuprofen with a glass of orange juice and then decided that a shower was what I needed. I passed through my bedroom en route to the master bathroom. Lynn had pushed the covers off of herself during the night and, apparently, she had awakened at some point because she had found one of my tee shirts to wear as a sleep shirt. She was splayed out on my bed, lying on her side, with her legs parted like scissors. Once again, I was treated to the wonderfully arousing sight of her camel toe and I felt Mr. Boing! coming to life. I was concerned about what Mr. Boing! would start suggesting if I paused to appreciate the scenery, so I grabbed my bathrobe and headed for the shower.

As soon as the water warmed up, I jumped in and started sudsing my body. When my hand grazed my member, it got even harder, reminding me - as if I needed a reminder - that I needed to get myself some relief before I got out of the shower and faced the scantily clad dream girl in my bed.

As I started stroking my man meat, I heard some noise in the bedroom and assumed that Lynn was waking up and getting out of bed. The next noise I heard was the bathroom door opening.

"Hey, I'm in the shower!" I cautioned her.

"Yeah," she replied. After a pause, she added, "I'm hung over, not stupid."

"Well . . .!" I challenged her.

"I need to pee and I can't see much through the frosted glass on the shower door and, besides . . . after the show you got last night, you shouldn't be complaining about the chance that I might see you naked."

"All I did last night is what was demanded by the circumstances," I defended myself.

"Hey, don't get too wound up about it. I'm just jerking your chain because I'm a little embarrassed about you seeing me with my panties around my ankles."

"I thought you were passed out!" I explained.

"I was, but it's kinda hard for a girl to stay passed out when somebody's rubbing her buzz button," she answered.

"Well, I didn't know if you had already wiped after you finished peeing," I offered in my defense.

"So . . . did you enjoy the show?" she inquired.

"Do you mean the beaver demonstration project downstairs or the naked beauty show upstairs?" I laughed.

"Both," she said.

"Lynn, you are the most beautiful woman I know. I wish I had a girlfriend like you," I admitted with the utmost sincerity. "If you were here in the shower with me right now, I might do something rather unbrotherly and show you just how much I appreciate your naked body."

"Careful what you wish for, 'cause you just might get it," she cautioned me. At that point, I heard the toilet flush. I could see that she was walking towards the shower door. Had she taken my last comment as an invitation?

I saw the shower door open and then her head came into view as she peered into the shower. She looked at my eyes and smiled and then she scanned down my naked body, her gaze coming to rest on my hard member.

"Very nice," she said as she continued to stare.

"So did you decide to take me up on my offer?" I asked.

"No, I just decided that since you saw me naked last night, I should have a chance to see you naked. Now we're even," she said as she pulled her head back and closed the door.

I heard the bathroom door close. I proceeded to vigorously masturbate my manhood and I came in powerful spurts that decorated the shower door before they washed down the drain.

I got out of the shower, dried my body, and put on my robe. When I exited the bathroom and walked back into the master bedroom, Lynn was sitting on the bed.

"Did you get that thing to go down?" she asked with a smirk on her face.

I didn't want to say anything too mean to Lynn but the frustration of this situation was beginning to get to me. "It's very unfair of you to tease me like this. I didn't make you get drunk and show me your camel toe with the wet spot and I didn't get you drunk so I could wipe the pee off your pussy and help you into bed last night and I didn't make you sprawl out in the bed this morning and give me another exhibition of your panties pulled tight against your shaved pussy," I said, and then I turned and left the room.

About thirty minutes later, Lynn came downstairs. She was dressed in the clothes she had worn the previous night.

She walked up to me, put her arms around me, and hugged me closely to her. "I'm sorry," she apologized. "I wouldn't admit this to anyone else but, you are my best friend so . . . I'm just feeling so sexually . . . needy . . ."

"It's called horny," I corrected her.

"Okay, me so horny," she said in a very bad impersonation of a Vietnamese whore. Resuming in her normal voice, she elaborated, "Actually, I'm so horny lately that I wanna fuck anything with a . . . anything with a dick, and I shouldn't have done what I did, but . . . I'll try to make it up to you, if you'll let me," she offered.

"What are you talking about?" I inquired.

"Well, you probably have plans for tonight, since you're Mr. Stud Muffin and it's Saturday night but, if you don't have any plans, come over to my place and I'll fix you dinner."

"Actually, I don't have plans and it's a date. What time?"

* * *

I arrived at Lynn's apartment with two bottles of wine. She put them on ice and we sat and talked as our dinner finished cooking. Right on time, dinner was ready and I had already noticed that Lynn had set a table like she was entertaining royalty.

"What's up with the fancy spread?" I asked. "Somebody else coming for dinner?"

"No. Do you remember telling me last night that I deserved the best?" she asked.

"Yeah," I responded, "and I meant it."

"Well, you deserve the best, too, and this is for you. I hope you like it." She kissed me on the cheek and then returned to the kitchen to get our meal.

We feasted on lasagna, salad, fresh bread, and apple crumb cake dessert. It was a meal fit for a king. If I had known the menu in advance, I wouldn't have purchased two bottles of white wine but . . . neither of us were connoisseurs and the wine was consumed without complaint.

After dinner, we retreated to her living room, accompanied by our glasses and what was left of the second bottle of wine. As I sat on the sofa, Lynn sat on the floor in front of me and started removing my shoes and socks.

"What's this all about?" I asked.

"I'm trying to make amends for teasing you last night, so just sit back and enjoy a foot massage," she said.

"I won't make you stop," I joked and then I got quiet.

SmallTitFan
SmallTitFan
1,969 Followers