CHAPTER 3: MY SEX DATE WITH A FORMER HAWAIIAN BEAUTY QUEEN

MONOGAMY SUCKS, A SWINGER’S TALE, Part 1
By George Pappas, COPYRIGHT, 2010

CHAPTER 3: MY SEX DATE WITH A FORMER HAWAIIAN BEAUTY QUEEN

October 21

A few days later, a woman who called herself Leilani, left a response to my ad looking to meet.

“I saw your ad. I wanted to know if you wanted to have some fun,” her message went. “I am thirty and curvy. Call me at 213 446-7892.”

I listened to her message a number of times and debated whether I would respond. However, my horniness soon enough overcame my doubts. It's my typical dilemma -- common sense and good judgment vs. lust. Seems like lust always wins out in the end.

October 23

I talked to Leilani on the phone today. She sounded extremely nervous and evasive. I figured this must be her first time doing something like this, but I didn’t ask her. She already seemed anxious enough about it. I didn't want to put her off.

She told me nervously that she was just looking for some fun, but didn’t elaborate on her definition of fun. I tried to make her feel at ease by reassuring her that I was looking for the same. I asked her what turned her on and she just said pleasure. Leilani wouldn’t talk about her desires or needs at all, and avoided saying anything directly about sex. It was not exactly a hot and sexy conversation.

“What do you look like?” I asked dreading her response.

She admitted she is a big woman weighing about 190 pounds. “Is that OK with you?” she added hesitantly.

My heart sank, but what was I going to say? I couldn’t turn her down for that. I’ve always been secretly attracted to fat women. I don’t know why. Maybe because it is such a taboo in a society obsessed with weight and achieving the perfect body. Or maybe I just like the thought of easy pussy from desperate women.

“Sure. I like women of all sizes,” I told her and I wasn’t lying. Really.

Frankly, I have some sobering thoughts about her resembling an enormous Sumo female wrestler or some circus freak and I am considering calling it off.

I am beyond horny, though. I have developed permanent blisters on my palms from taking care of myself too much, and I am tired of it. I want to feel the touch of a woman again. My standards will have to be discarded for a night. I can’t wait any longer to get laid. I am drowning in my own come. Nothing relieves my hungry lusts. I am so bored of jacking off to porno films. It just makes things worse when you’re horny and lonely. That’s hyperreality sex anyway. I mean come on. Where do you find uninhibited women like that in real life who will do everything you can imagine sexually? Isn’t this what my sexual quest was all about: to find those kind of wild women? Maybe Leilani was one. Who knows? So I am determined to end my dry run.

October 24

The next night I drove to meet Leilani at an ugly brown stucco house located off Santa Monica Boulevard on the outskirts of Beverly Hills.

She told me it is the residence of an elderly woman she is taking care of. Leilani works as a live-in nurse, and her patient was visiting relatives so we had the house to ourselves.

As I walked up the driveway toward the house, a stocky Samoan woman opened the front door and nervously asked me if I was Jake. She didn’t lie on the phone. Leilani is a big woman, and honestly she could have been a Sumo wrestler in training. She is short about five feet tall and I figure weighs more than 200 pounds. She had put her black hair in a bun, which only emphasized her large face and features.

She led me inside the house and into a dimly lit ornately furnished living room. Leilani flashed her smile at me for a moment -- quite literally -- both of her front teeth had garish gold caps. After seeing that, I had a strong urge to leave. Up close, I also realized she is older than she said on the phone. Wrinkles around her eyes made her appear to be in her late forties maybe even early fifties.

Leilani wore a turquoise dress that was too small for her and her black stockings also seemed out of place on such a huge woman. She kept fidgeting with her dress and appeared uncomfortable. She was no doubt a fuck date virgin. Yet she could have been hornier than I was. She had dressed up for the occasion and obviously wanted something to happen on this night even though I could tell this was a situation unfamiliar to her.

I had fucked worse (at least I think I have), but was this how I wanted to start my journey? Fucking an obese woman? Although I was horny, I still wondered if I could do anything sexually. It was one thing to fantasize about fucking a stranger, but it was another thing to actually go through with it especially with a woman this big.

I felt awkward, too, but struggled not to show it. What had I got myself into? Despite my misgivings, she actually did attract me. Most of my friends would die laughing if they knew I even considered fucking this behemoth, but my cock had other ideas. I felt a glimmer of desire as I looked her over. I had fantasized about fucking Hawaiian women, but those were usually the ones you see in Playboy pictorials or tourist photos. They were all much prettier not to mention thinner than Leilani.

Well, as my dad used to advise me when I was growing up: “You got to start somewhere.” However, I don’t think he had someone as heavy as Leilani in mind when he said it.

We stood in the dark living room and struggled to make small talk. I didn’t sense any real hot chemistry between us. I thought I better figure out a quick excuse to leave in case this went south. I didn’t want to waste too much time if I wasn’t going to get laid. So I asked her what she wanted to do. She smiled awkwardly at me and said anxiously once again that she just wanted to have fun.

“OK,” I said. “Where do you want to go?"

She glanced at me pensively and then silently led me to a sparsely furnished room at the back of the house that had a bed. As Leilani turned her back to me and faced a mirror next the bed, I watched her undo her hair clip and let her long black hair flow down. I took it as a signal to make my move. Despite my nervousness (my hands were shaking for fuck’s sake), I slid up behind her and kissed her neck. She smelled good which got me hot.

Leilani turned around to face me and we kissed briefly. Her lips were dry and rough. Leilani then grabbed the back of my head and kissed me aggressively. She seemed starved for affection, any kind of affection. I gently pushed her on to the bed and rubbed my body against hers. She is enormous, and I didn’t know where to start, but I was aroused. My cock throbbed in my jeans.

Leilani sat up on the bed and started removing her dress, stockings and panties revealing her huge naked body. Her large breasts sagged and drooped against her flabby enormous stomach, and her huge nipples hung down like small dark sagging heads. I tried not to look too closely at her flabby nakedness. I asked her to lie back on the bed and went down on her. I hoped my oral skills could be the ultimate icebreaker and turn around this sorry sexual adventure. She has big brown pussy lips and matted black pussy hair. Her pussy looked strange and misshapen, and I had difficulty locating her clit. So I took the plunge and braced myself for a bitter pussy licking experience, but I was pleasantly surprised as she didn’t taste harsh at all.

In response to my attentions, she began making deep grunting sounds followed by wheezing moans and sighs.

“It has been a long time…ooooo…a long timeeeee,” Leilani exclaimed. “Make me come…make me come…make me come. “ She kept repeating that phrase like a sexual mantra as I licked her faster.

Listening to her pleasure got me aroused, too. However, I realized too late that I was enjoying myself a bit too much. I got so excited I came hard in my pants while my tongue probed her pussy. I had already shot my wad much to my shock and disappointment. I was quickly overcome by what I can only describe as “post-come depression”. I didn’t want to tongue out her pussy anymore. I felt tired and empty, and suddenly I just wanted to leave even though I had only been there for 10 or 15 minutes.

I tried pretending that I was still aroused and interested in eating her pussy, but it was no use. I had lost my desire. I was hoping she hadn’t noticed as I continued tonguing her pussy until she told me to stop. I didn’t ask if she had come. I really didn’t care at that point. My sexual fire was gone and I was frustrated with myself. This what happens when you don’t get laid enough. Just eating pussy is enough for me to get off. I have no self-control right now. I need more sex to build up some kind of sexual stamina.

Shortly after my premature ejaculation (in my pants!) episode, we were both lying naked on the bed and she started sucking on my cock. Maybe she noticed I had come, but she didn’t let on. For the life of me, though, I couldn’t get hard for her.

Leilani looked up at me for a moment and asked me if I wanted to fuck her doggy style. Now, she had my flaccid cock in her mouth and yet she still thought I could do it. I had to admire her for that. She turned around and stuck her ass out for rear entry. There it was in all its enormous glory: her huge flabby ass, which was anything but inviting. There was so much ass I couldn’t see her pussy. Didn’t matter, though. I grabbed a hold of my limp cock aggressively and tried to fuck her in vain. It was ridiculous. My cock was useless. It was a flat tire, a deflated balloon. It was a dead cock hanging.

She looked back at me, grinning with her gold teeth, and mumbled softly, “We aren’t going to fuck are we?”

She didn’t seem angry, but I detected some frustration in her voice. Leilani had probably waited a long time to connect with someone, anyone. I was not exactly fulfilling her fantasy with my limp cock. I tried not to think about it and rested back on the bed as I was at a loss for words.
Perhaps sensing this, Leilani lay down next to me on the bed and proceeded to describe her former life in Hawaii. It was too early to go home so I had no choice but to listen. The trick was to pretend that I was interested. She hardly noticed. I think she liked listening to the sound of her own voice.

When she was 20, she had been a beauty queen in Hawaii even showing me the pictures as proof. In one of the photos, a much younger and thinner version of Leilani was featured posing in a bathing suit during a beauty competition. She was very attractive. What happened? She had really let herself go. I looked at her closely and tried to find traces of the beauty queen in her plump face and body, but little of her former self remained. Her eyes are still pretty as in the pictures, but there’s sadness in them now. Things obviously hadn’t turned out as she expected.

As she told it, everything went downhill after her beauty pageant days. She got married and had two kids and was later divorced. Out of depression and loneliness, she turned to food for solace and soon her weight got out of control.

It had been more than three years since she had been with a man sexually. Then she admitted sheepishly that she is 49, which I already guessed was true.

She has a lot strikes against her: her size, her age, but still I liked her. At least, she didn’t bust my balls about not being able to fuck her. Still, I wasn’t leaving until I penetrated her pussy with my cock. It was a matter of pride for me.

While she talked about her past, my cock gradually came back to life. I slid my hands down her large belly and groped for her pussy. I played with her clit and finger fucked her, and then I pulled my fingers out of her pussy and stuck them in her mouth. Leilani hungrily sucked on my fingers and smiled at me.

I was feeling anxious and wanted to fuck her before I lost my erection so I crawled on top of her large body and tried unsuccessfully to enter her. I was hard enough, but she was just too tight. I couldn’t seem to part her lips. She reached down and grabbed my cock and after some effort I slid inside of her. Unfortunately, I quickly shot my load following several thrusts into her tight pussy. I lasted a whopping twenty seconds. Just call me lightning. Typically, I had more staying power after my first orgasm, but that was before my recent dry spell.

As I rolled off of her, I apologized for my lack of stamina. Much to my surprise, Leilani blamed my quick trigger on her pussy being so tight.

“I am sorry. I haven’t had sex for a long time. I am too tight,” she said grinning and acting embarrassed.

Incredible, I thought. She is apologizing for being too tight. A woman can never be too tight.

We talked for a while longer and then my post-come depression returned. I was restless and wanted to leave as she rambled on about her family in Long Beach (where there is a large Samoan community), her failed marriage with her ex-husband and how much she missed sex. I smiled and pretended to care, but I knew I didn’t want to spend the night with her. I was already bored and I didn’t think I could fuck her again.

Finally, when I couldn’t listen to her bullshit anymore, I blurted out that I had to get up early in the morning for work. I lied. I had taken the day off from work anticipating spending the whole night with her. Now that was not an option. I felt suffocated in that small bedroom listening to her talk about her lonely life.

She briefly gave me a sad look and then quickly covered it up with a smile, but I knew she wanted to keep talking and fucking all night. Her dry spell had been a lot longer than mine and she was no doubt hoping to finally avoid another lonely night.

I reached over and touched her arm and told her I’d call her again. She nodded and said it was all right, but I knew it wasn’t. I told her a second time that I would call her, but got the feeling she didn’t believe me. Honestly, I doubted if I would. Now, that I got my rocks off I wondered what was I thinking? She wasn’t the girl of my fantasies. How hard up could I be to fuck her? I felt pathetic. I was in the throes of my post-come let down and I had to get out of there fast.

Leilani walked me to the door and kissed me goodnight. She gave me one final look of disappointment and shut the door. I left feeling mixed up and confused. I was glad I had ended my pussy drought after so long, but I felt guilty about her sadness. I had been given more of a glimpse into her lonely existence than I had wanted to.

It was a strange sort of intimacy between us – short but also tinged with a depressing desperation. Our sexual encounter should have made me feel less alone, but instead it had the opposite effect. I wanted nothing to do with her desperation. I had enough of my own to deal with. She also bored me to death and was hardly hot in bed. I couldn’t bear to call her again.