The Scotsman's Inn

Early spring of 1979 arrived, my girlfriend and I had broken things off. It was not that we were moving in any direction as a couple. It was a relationship based solely on convenience at the time. Obviously, she wanted some direction that I did not.

In mid-May, all the employees of the company I was employed by. Informed the employees, that the company was filing for bankruptcy. At twenty-two years old, I was without a girlfriend or a job. I spoke to my parents about my predicament. We came to an agreement that I could move back into my old room. However, I would have to find employment and pay seventy-five dollars a week towards expenses.

With this convenience of situation I came to the decision. I would get a night job, and pursue my passion of surfing for the entire summer and into early fall.

One of the positive aspects of living near the ocean is a wealth of beach bars. One in particular, "The Castaway's" catered to a younger crowd. It was essentially a meat market; the women were young and attractive. But for a horny young man it was many more strikeouts than homeruns.

One of my surfer friends, Larry. Who was older than us by about twelve years, was divorced and ran a successful business. He and his ex-wife had no children, so his divorce involved a lump sum payment to his ex-wife. Which left him no strings attached to his former spouse.

Larry suggested we stop at a bar a few miles inland, named The Scotsman's Inn. The Scotsman's Inn was a divorcee bar and hookup location. It was here that I discovered the joys of being a younger man sexually involved with older women.

There were many memorable evenings from The Scotsman's Inn. This story is only about one of them. This particular experience didn't happen on my first visit to The Scotsman's Inn. I had probably been there ten to fifteen times already. Given the chance to go back in time, I would probably go back to this night.

Larry and a few other surfer friends agreed we should each go home and shower and shave. Meeting later at the parking lot of The Scotsman's Inn approximately 8:00 PM. After all, most women wouldn't be interested in grubby and sweaty men.

It was approaching 10:00 PM one Sunday night. The people in The Scotsman's Inn were thinning out. Most of my attention always centered upon women from their early to mid-thirties. I went up to the bar to get my last drink of the night. To the left of me, several feet away sat a woman who was fifty to maybe mid-fifties.

Her drink was down to the ice cubes and she was nursing a cigarette. I ordered my drink and as the bartender turned away to make my drink. She said to me "Didn't your mother raise you correctly. Why didn't you offer to buy a lady a drink?"

When the bartender returned with my drink. I said, "I would like to buy a drink for the young lady next to me." As the bartender turned to make her drink. I told her that I would be right back; I left my drink at the bar. Then went to tell my friends to leave without me, we always drove our own cars just in case you met someone.

I returned to the bar and extended my hand, "Hi, my name is Greg." She grasped my hand lightly and said, "My name is Connie." I asked her if she would mind if I took the stool next to her. She told me she would not mind at all, over the next hour or so we made small talk about our lives.

During the hour, we each moved closer to one another. She reminded me of Ingrid Bergman in Casablanca. The scent of perfume, cigarette smoke and alcohol on her was an aphrodisiac for me. As time passed, we punctuated our conversation with glances and touching each other's arms or shoulders.

At a bit past 11:30PM or so, I thanked Connie for the pleasant conversation and said I must be going. She told me that she should get home too, so I offered to walk her to her car. After her remark about lacking politeness, I wanted to prove her wrong about that.

Our shoes made a crunching sound as we walked across the gravel parking lot. At that dark and quiet hour, the sound seemed much too loud. I thanked her once again and asked if I could kiss her goodnight on the cheek. Connie said she wouldn't mind at all. We each leaned in for a kiss on the cheek. After we kissed, we each lingered and then our lips met. All our pent-up sexual desire flowed like electricity between us.

In a low husky voice, she asked me if I wanted to join her for a nightcap at her house. As I followed her the few miles to her home. The thought of being with a woman thirty years older than myself, was making my head spin. My erection felt as if it would snap off before we arrived at her house. As soon as we entered into the front door, our lips and hands were all over each other.

Connie told me to make myself at home on the couch and that she would be right back. She went down the hall and returned in a few minutes. I was glad to see that see didn't return in a negligee. Because as much as I like a present, I would enjoy unwrapping her from the clothing she wore to the bar even more.

Connie sat next to me and we began to kiss again. I placed my hand on her breast outside of her blouse. Her hand rubbed my erection through my pants. I started to kiss her neck; she asked me not to give her any hickeys. Then she whispered, "Would you mind if my mother watched us?"

I sat bolt upright almost instantaneously. The look on my face must have betrayed my true thoughts and feelings. Connie put her hand on mine, "Greg, I know this is an unusual request. Just meet my mother, if you want to leave. I'll understand and won't harbor any bad feelings toward you."

There are moments when your brain can calculate hundreds of scenarios simultaneously, and this was one of those moments. I quickly assessed different options for myself. I quickly settled upon, if I was being setup somehow. I was most likely younger, stronger and in better physical condition. Then whomever might try to rob me or cause me harm.

If this whole thing was real, the worst option. Would be a nice blowjob while mama watched her daughter go to town on me.

In the least nervous voice I could muster, I said, "Okay, I'll meet your mother and let her watch us."

Connie retreated down the hall to what must have been the kitchen and bedroom portion of the house. I heard the creaking of the floor as they approached the living room. So I decided to standup, to greet her mother or make a break for the door. Should this be a planned robbery or something else?

When Connie's mother entered the living room. The woman that entered the room shocked me. Connie said, "Greg, I'd like you to meet my mother, Stella." Connie was probably very attractive when she was young, her mother must have been an absolute knockout.

Stella appeared to be twenty years older than Connie, perhaps a few less. She had some small wrinkles around her mouth and eyes. I gave a quick look to her figure and she was still shapely. I could vaguely make out the outline of her nipples through the cotton nightgown she wore. "Hi Stella, it's nice to meet you." I said as I gently grasped her hand.

Connie broke the ice by asking, "Would anyone like a drink?" Almost too quickly, I blurted out "I'll have a gin and tonic!" Everyone laughed at my outburst and it seemed to lighten the mood. Both Connie and her mother retreated to what I presumed was the kitchen to make the drinks.

I was glad Stella accompanied her daughter. Because I wouldn't have known what to talk about with her mother. Also, my mischievous mind was racing with thoughts of what they might be talking about.

Connie and I sat on the couch while Stella sat across from us in a chair. Connie rested her left hand on my right leg. As the minutes passed, Connie moved her hand closer to my cock.

Being a normal twenty-two year old male. It didn't take too much for my dick to get rock hard. Once she reached my cock, Connie began to use her fingernails. To tease me even more through my jeans. My mind had already be racing, thinking about how this daughter. Had come to the point of letting her mother watch her have sex with men?

I reached the point where I no longer cared who was watching us. I just wanted to bury my dick inside this sensual older woman. I pulled Connie close to me, our lips met and within seconds tongues danced. I groped her tits through her blouse and bra.

As Connie and I continued our foreplay, I unbutton her blouse so I could cup her tits and play with her nipples. A few short minutes later she unbuttoned my jeans and unzipped my pants. Connie started rubbing my dick through my underwear. As inconspicuously as possible I glanced over at Stella. She was squirming around in the chair a bit, but wasn't touching or playing with herself in any way.

I pulled Connie's blouse from where it was tucked into her pants and unbuttoned it completely. Thankfully she had a front clasp bra on, which took seconds to open. I slid both from her shoulders so I could suckle her tits. Her full-sized B's fit her frame perfectly.

Connie stood up and prompted me to stand up too. She unbuttoned my shirt and ran her hands over my chest, circling my nipples. Then she reached into my pants, pushing them and my underwear down. My erection sprung free for both Connie and her mother to see. She knelt on the floor in front of me. Pulling my pants and underwear down, she held them so I could step free.

Connie wrapped her fingers around the shaft of my cock. Slowly she began orbiting her tongue around the head of my dick. Switching direction every minute or so, she then started using her lips to tease the rim of my cock's head. From the tingle I was feeling in my balls, I knew it wouldn't be long before I lost control. Being young and horny, I knew I was capable of cumming two or three times. The devilish part of me thought "If her mother wants to watch a show. Then a show she will have."

I reached down, urging Connie to stand up. I grasped her pants, pushing them and her panties down to her ankles. I held them so she could step free, then tossed them aside. I stood wrapping her in a tight embrace. Our lips locked into a kiss of deep passion; Connie was no passive lover. As she pushed her tongue deeply and forcefully into my mouth.

In the heat of the moment, I'd forgotten completely about Connie's mother watching us. With one hand Stella was playing with her nipples. Her other hand was between her legs, with her legs tightly clamped together. Now it was Connie's turn to get some oral stimulation from me.

I gently, yet firmly guided her to sit on the couch. I pulled her hips forward until her sweet pussy was at the edge of the couch. Placing her legs over my shoulders, I began kissing her inner thighs, moving closer, then further from her pussy. I had learned from another mid-thirties' woman. That men are usually too quick and rough, reaching to give their lover an orgasm orally. So even though I was practically raging sexually to give Connie an orgasm. I forced myself to slow down and hopefully give her a more intense experience.

From where Stella was sitting, I knew she couldn't actually see me eating her daughter's pussy. Silently, I hoped she would sit on the couch next to Connie. But that wasn't in the cards unfortunately. So, I had to hold onto hope that things would take a kinkier turn later on.

Stella could only use her imagination as to what Connie was experiencing, by watching and listening to her reactions. Resisting the urge to dive right into her, devouring her pussy. I slowly kissed closer towards her outer labia. Occasionally, I barely brushed against them using the back of my hand. Connie was beginning to squirm around, so I knew she was ripe for the picking. I slowly worked the tip of my tongue between her swollen outer pussy lips.

I slowly and rhythmically moved my tongue to and fro along her glorious slit. Slowly increasing the length and depth my gustatory organ. Stopping precariously close to Connie's puckered butthole. Then traveling northward to occasionally circle her clit, sometimes once, sometimes several times. Often, I wouldn't even touch her clit. I wanted to keep her hungry and guessing as to what was next.

I believe most younger or less experienced women would have succumbed sooner to my oral acrobatics to their love nest. Many women my own age would have already orgasmed. My jaw and tongue were beginning to give out.

Just as I thought all was lost and I should just give up. I began hearing Connie's soft and plaintive moans of "Yes, oh yes."

Connie began to rock her hips, her hands cradling my head. As if to steer me towards her most needy points. Connie's vocalization became louder and more urging. I imagined, because I couldn't see. That Connie's mother, Stella was close by watching. Perhaps only one of two feet, watching my cunnilingus assault on her daughter's pussy. I also wondered if Stella's fingers were circling her own clitoris, imagining it was my tongue or that of a former lover.

Connie's continued urging me on. But her words were interspaced with gasps for breath. Finally, she began a quiet almost suppressed squeal as her pussy drenched my face. I tried to continue feasting upon sweet vagina. But Connie pushed my face away saying, "No, no more. Please."

I looked towards where Stella was sitting in the chair. Stella's nightgown was bunched up. But she sat at a slight angle, so I had no chance to look up her nightgown. I was desperate to see her pussy, or at least the effect my and her daughters show was having upon her.

My cock at this point was probably harder than it had ever been. My dick is not disproportionately large, such things are a coin toss of nature. But I was blessed with the ability of staving off cumming for a good long while. With how turned-on Connie had me, I was going to need every bit of that talent.

Random sexual encounters are about one thing, animalistic fucking. Neither person knows or has learned each other's sexual nuances. Now was time to put the broom into the broom closet.

Now was the point of the evening where I would take control of the love making. I certainly wanted to satisfy Connie, but right at that moment. I wanted Stella to get the show she was looking for.

With Connie recovered enough from her orgasm. I placed my hands on her hips, urging her to slide down a bit further on the couch. Connie raised her legs up and I grabbed my cock. Running the head along the length if her slit. I teased her clitoris with the head of my cock. Then ran it slowly towards her puckered little butthole, even rubbing across it. I did this several times until Connie said "Are you going to tease me or fuck me?"

Which was exactly what I was waiting for. I wanted her cunt starving for cock and a good fucking.

I wiggled the head of my circumcised cock right at her entrance. Slowly I entered her until the rim of my cock head was just barely inside her. I then withdrew it, never letting my dick lose contact with Connie's pussy. I repeated this several times, I wanted her sexual anticipation and frustration to build.

I began to go slightly deeper each time. But I also mixed in times when I would almost pull out and times I would withdraw completely. Always being mindful not to let my dick lose contact with Connie's pussy.

My balls ached for release, but I was trying my best to forestall the point of wild abandon. Because like most men, once I began fucking like a runaway locomotive. There was no turning back.

Connie's pussy felt exquisite as it enveloped my cock. I closed my eyes and lost myself in that feeling alone. A small creaking sound startled me from my thoughts.

"Shit!" I'd completely forgotten about Stella watching us! Stella wanted a show, I was going to give her the grand finale of the show.

I took my arms and hooked my elbows behind Connie's knees. This allowed me to move her legs further back and wider. Which in turn pivoted her hips upward, raising the height of Connie's pussy. While also changing the angle, exposing her pussy for a better view.

I couldn't believe how wet my cock was as I rhythmically plunged into Connie. Over my right shoulder, I noticed Stella was standing up to get a better view. I made sure I took the longest strokes I could. So, Stella could witness me plunging my piston into her daughter. I was truly hoping that Stella would even in some small way, join in.

Unfortunately, I realized my fantasy wasn't going to come to fruition. So being the hour was getting late. I concluded I'd better bring closure to the evening. The skorking sounds that Connie's sopping wet pussy was making. Drove me to the very threshold of climax.

I decided that if I could, I would shoot my first shot of cum into Connie's cunt. Then pull out and stroke my cock. Shooting everything else wherever it may land.

As my balls began to boil over, I said "I'm cumming!" Connie let out a squeal and I believe my announcement triggered her orgasm. I shot my first rope of jizz as I was on the outward direction. So I pulled out of Connie and began stroking my cock furiously. Three or four more ropes of cum landed on her stomach and tits.

I was physically spent, and collapsed forward onto Connie. I kissed her passionately and deeply.

Since this wasn't the cuddle in the afterglow type of sex. I got dressed and said goodnight to Connie. I told her I had a wonderful evening. Also, that she was a fantastic and passionate lover. I said goodnight to Stella and kissed the back of her hand.

There were other evenings of drink and debauchery at The Scotsman's Inn. I'd often hoped to see Connie there. I did see her a few times, I would always go up to the bar where she was sitting. I would always say hello and buy her a drink. Sadly, she never asked me to accompany her again.

In all the years since that night. I have asked myself a million questions about that evening. The how's and why's of Connie's and Stella's relationship? The how and why it all began? Connie putting on a show while Stella indulged voyeuristic behavior. Did Stella ever join in?

To this day, this remains one of my favorite memories.