Sasha

I hadn't seen Sasha in close to six months so I was surprised to receive a text from her asking to get together at a local bar after work one night in February. I was purposely twenty minutes late because a) she is notoriously late and b) I wanted to walk in and see her waiting for me. She did not disappoint. She looked absolutely incredible seated on a bar stool. Sasha is of Asian and Portuguese descent and just simply gorgeous, dark complexion, high cheekbones and vaguely Asian features along with long straight shiny black hair that she could shake, flip or otherwise move to melt my heart. The thing that I most loved about her was her easy, almost childlike exuberance. That night she wore a tight, long sleeved black knit dress that ended well above her knees, black patterned stockings and tight light brown suede boots that ended just above her knees. She almost always wore tight clothing. As is her norm, there was the smoldering eye makeup and the glossy lips. Again, as is her norm, she wore no jewelry. And I knew that once I got close to her, there would be the intoxicating scent that she always wore. I paused in the doorway just to admire her until she caught my eye.

At 54 years of age, I am twenty five years older than she is. Further I am married and she is not although she always seems to have a boyfriend or two who are of questionable character. While she has never specifically admitted it to me, I always suspected that she has had a few girlfriends over the years who were more than BFF's. Sasha has the ability to cultivate relationships both personal and business with virtually anyone of any age, gender, race, ethnicity or social standing. She is one of those girls that everyone who meets her is drawn to. Further she is perpetually broke, usually impossible to get a commitment from and likely the most irresponsible person I have ever met. But all this only adds to her charm.

I was working in a corporate position when I interviewed Sasha for an entry level job. At 24, she was two years out of a good college but had not had any relevant work experience, just waitressing, bartending and retail. Normally, I would not have given someone with her background a glance let alone an interview but her resume and cover letter were extremely well written and somehow extremely feminine so I asked the HR staff to bring her in. Perhaps part of my motivation was just to be an older man leering at a younger woman. She just blew me away in the interview with her carefully researched knowledge of the company, the company's business and competitors and her computer skills. And yes, she was very easy on the eye. And yes, her personality might have won me over. Over the four years that she worked for me, I found that she had an incredible work ethic, terrific attention to detail, really good figure aptitude, almost photographic memory and great organizational skills all of which were in sharp contrast to her personal life. She also became exceptionally loyal to me. Always polite, I knew that she appreciated both the initial opportunity and the mentoring that I provided. Occasionally when working late we casually flirted but I think we both realized that we had to keep the relationship on a professional level. The only flaws that I noted were the occasional emotional meltdowns related to her personal life and the constant lack of funds despite the handsome salary and bonuses that I managed to get for her.

I eventually decided on a career change and left my position and Sasha behind. We stayed in touch via text, email and very occasional phone calls for a year. I also saw her several times at gatherings of former colleagues. At these gatherings we always were drawn to each other and flirted more than we ever did as boss and employee. I found that I missed her more and more and I suspected that she did too. We had established a bond along with a mutual respect that would never go away.

After I had had a few drinks one night when my wife was away, I impulsively called her without texting first, a violation of protocol with Sasha's generation. Surprisingly she picked up and then surprisingly ignored my somewhat inebriated state. After some catching up, I proposed a weekend trip to Cape Cod with the provision that I would get a room with two double beds. I mumbled something about not wanting to get involved hoping that she would perhaps naively think that I wasn't looking for sex. She clearly was taken aback but after moment, said she didn't have the money. After I assured her that I would pick up the tab for everything, she somewhat unenthusiastically agreed to go in a month's time. Given her unreliability, I almost wrote off the possibility of her going as just being her usual polite self and not wanting to say no to a drunk.

I didn't hear from Sasha for two weeks so I emailed her details of where I wanted to stay expecting a sorry, but I can't go response. What I received back was a detailed list of what she wanted to do, several restaurants that she thought were promising, the beaches that she wanted to go to, and the wonderful theater and play that she wanted to attend. Again, she had meticulously researched the Cape as she had done the company when I first hired her. I immediately made reservations for both the motel and the theatre and then masturbated thinking of her.

Sasha's text messages became more numerous as we got closer to the day we would leave. She clearly was as excited about going as I was. We agreed to drive up on Friday morning and leave Sunday afternoon. I arranged a plausible explanation for my absence with my wife. While Susan had met Sasha many times over the years and adored her as everyone else did, she did not suspect that I had a crush or worse on her.

The weather forecast for that early September weekend was sunny with temperatures in the low 80's with a chance of thunderstorms, just a great beach weekend. I picked up Sasha at the apartment that she shared with her roommates at 10:00 and we began the three hour drive to the outer Cape. Over the years that I have known her, Sasha always dressed impeccably in business or social situations. I always suspected that most of her money went to clothing. I was somewhat surprised to see her dressed in a simple tank top, shorts, cheap flip flops with her hair tied back in a pony tail. She wore no make up that I could discern. Regardless, she looked terrific and could have passed for a college student despite being in her late twenties. Perhaps that childlike exuberance that so attracted me was even more in evidence. We had some wonderful conversations on the drive about music and sports among other things. I had had some nagging doubts about the weekend becoming a disaster with me being unable to relate to someone as young as she was but those worries quickly were dispelled. I had decided that I absolutely would not hit on Sasha. I would simply play the paternalistic role unless it was very clear that Sasha wanted something more.

We arrived at the motel and found it to be more than satisfactory. Rather than having the promised two double beds, it had two queen size beds. We both quickly unpacked and headed for the ocean side beach after a quick stop for beer. Sasha loved the wide open beach and the surf. We both alternated between reading and swimming and I tried not to stare at her incredible body barely covered in a white bikini. We stayed a few hours until hunger got the best of us. Back at the motel, I showered first and changed and waited for Sasha to do the same. She dressed in the same clothes that she had worn on the drive up which were appropriate for the casual restaurant that she had chosen. Dinner was a delight as Sasha had raw oysters for the first time. I just loved being with her as she discovered new things. After dinner we enjoyed a sunset and returned to the motel. We were both tired and spent the evening watching television and enjoying each others company each on separate beds. Bed time eventually arrived and I simply stripped down to my under wear and got under the covers. Sasha disappeared into the bathroom for a minute and returned in a long t-shirt. What followed was weird. Despite being tired, I was not able to sleep nor could Sasha. There was a definite tension in the room. After what must have been an hour, Sasha softly asked if I was sleeping. When I replied that I wasn't, she got up and crawled into my bed. She snuggled up next to me and told me how much I had meant to her over the years and how much she loved me. There was somehow nothing remotely sexual between us but the tension we both had been feeling dissipated. We quickly fell asleep tangled in each others arms.

We both slept late and after breakfast, hit the beach again. This time Sasha wore an even smaller white thong bikini that provided minimal coverage of her small breasts. As a boss, I never could comment on how an employee looked and I had continued that practice after I was no longer her boss. Now, I just had to say wow and I may have drooled. She simply responded by giggling. We both read and swam and enjoyed the warmth of the sun as we had the prior day. In the afternoon, Sasha asked if I thought anyone would mind if she took a walk away from the other beachgoers and smoked some weed. When I replied that I thought that it would be okay, she asked me to join her. It had been a long time since I had smoked and back in the day, I remember getting easily getting out of control and generally acting stupid. These days, I pride myself in always being in control. I cautioned Sasha that I might say something inappropriate if I got stoned. She giggled and said the she hoped that I would. She then shocked me by asking if I thought that it would be safe for her to go topless once we walked far enough away from the other people. I replied that I was concerned about sunburn on her presumably white tits. Her response was to pour sunscreen in both hands and massage her boobs under the bikini top. She clearly spent more time than necessary doing so. Needless to say, several nearby people got quite a view. Once done, she pulled a pot pipe, lighter and a small bag of weed from her bag and deftly tucked all into the pocket of my swim suit.

On the outer cape, the ocean side beach runs for forty miles. There are periodic access points but you can get away from the crowds if you are willing to walk. After walking a while and gabbing as we had become accustomed to doing, Sasha somehow reached into my pocket for the pipe and weed and motioned that we should sit down. We continued to gab as she filled the pipe, lit it and drew in deeply. She took several hits and passed it to me. Being unaccustomed to smoking I repeatedly gagged but soon started feeling wonderful. We both got incredibly giggly. Eventually, she reached behind her back and untied her top and asked what I thought. My immediate reaction in my stoned state was to try to clumsily touch her small breasts with the very erect nipples. She immediately took fake offense at my gesture and raced towards the water with me in hot pursuit. We swam in the surf for a good hour with just an occasional accidental touch. Periodically someone would walk by and it became a game for Sasha to stay underwater or face away from the beach until they passed although her tiny top was in pain view on the beach.

The sky started to darken in the west and we heard a few claps of thunder so we reluctantly dragged ourselves from the water. After grabbing the pot and her top, we started walking back towards where we had left the rest of our stuff with Sasha still topless. We walked silently now and Sasha no longer cared if someone saw her. The dark clouds soon became a wicked thunderstorm and we both starting running with Sasha's small firm boobs barely moving. We quickly packed our stuff and ran up the stairs leading to the changing rooms and parking lot after both putting on a t-shirt. After getting into dry clothing the rain suddenly stopped and we realized that neither of us had eaten since breakfast.

There was a great barbecue joint a short drive from the beach. Given our famished state, it was a wonderful choice. Sasha is one of those people who doesn't consistently exercise but always has a big appetite but somehow maintains a small but not tiny waist line. Still a little stoned, we quickly put away a dozen raw oysters between the two of us before moving on to a main course.

During dinner, she asked me what I intended to wear to the theater. Pants and a shirt was my brief reply. Then she asked if I would mind if she wore a dress. How could I respond other than affirmatively? I would have liked to have stayed in the bar of the restaurant for a while longer but she was insistent that we go back to the motel so that she could get ready. She very sweetly asked if I could take a quick shower first and then if I could leave for an hour or so while she got ready. Again, how could I say no?

When I went back to the motel at the specified time, I half expected Sasha to be still getting ready and in fact she was still in the bathroom. When she did come out of the bathroom, I was in awe. Very short, very tight reddish pink club type dress that really, really emphasized her ass. Low cut without really showing much cleavage of which Sasha really didn't have any. Matching high heeled sandals, nails and lipstick. And oh those eyes, she really knew how to apply eye make up.

"You all set to go" I asked

"Ahem, how do I look?" was her response

"Hmmm, pretty hot"

"You know, I understand and respect that you're married and I love Susan and I know that you do too and all that, but I would really really like it if you hit on me a little even if it's just a complement on how I look. I slept in the same bed with you last night and I went topless on a beach and all's that I get from you is a "hmmm, pretty hot". You wouldn't have asked me up here unless you had a strong interest in me."

I guess I finally became convinced that she did in fact want me to hit on her to state the obvious.

"You are the most beautiful woman that I have ever known, both physically and mentally. And right at this moment you're beyond the sexiest woman that I ever could have imagined. You look absolutely incredible." With that, I held her hand in mine and lightly kissed he lips. We stood lightly kissing each other for a good ten minutes, both getting excited. I finally broke away.

"Wow, that was special." she said. "Ooo, you have lipstick on your lips and cheek"

"You know, I kinda like how it looks on you."

"You never told me that" she pouted. "If I had known I would have worn it every time that we were together. I've always loved trying to attract you and keeping you interested in me."

"I was always interested in you and always will be regardless as to whether you are wearing lipstick. Perhaps just a little more interested when you have a fresh coat. Anyway, let's go or we'll be late"

Sasha grabbed a damp face cloth and wiped the lipstick from my face and we were off. Once in the car, she made a big show of reapplying an especially heavy coat and making sure that I approved of it. While kissing her, I had wondered if she was wearing any underwear of any kind. Her short dress kept riding up in the passenger seat and I periodically looked over. She caught me looking and tugged it down.

"It's not polite to stare"

"I know, but you have great legs"

"Are you trying to see my panties? If so, you will be disappointed because I'm not wearing any."

I could only smile and kiss her cheek. And that made her smile.

Sasha drew all kinds of attention at the theatre. Some older ladies clearly disapproved but mostly people stared for just a short time. And I'm sure that a few thought that perhaps I had hired her as my date. We managed to get aisle seats and I sat on the aisle to shield her from the attention. And yes, the dress did ride up but I couldn't really see anything in the darkened theatre. The play was hilarious and extremely clever. I soon forgot how she was dressed and we just laughed and giggled and talked about the play with just a little hand holding when the action slowed.

Once the play ended and we were back in the car, I asked Sasha if she wanted to go for another walk on the beach. The thunderstorms from earlier in the day had cleared out and it was a pleasant, still, warm moonlit night.

"I can't walk on the beach in heels"

"Hmmm, most people walk barefoot on the beach."

"Will you take my shoes off for me?"

"Oh all right" I said knowing full well why she wanted me to take them off.

So of course when we got to the beach, she sat in the car while I stood outside through the open door. And yes, her skirt rode up and I was treated to a view of the prettiest shaved pussy imaginable while I unbuckled her shoes. Even lit by just the car dome light, it seemed puffy and moist and I thought I saw a rivulet of moisture on her thigh. She in turn made sure to grind her feet into my groin. We walked hand in hand and later with arms around each other. We smoked a bit more weed, just enough to feel good without getting stupid. I was incredibly excited. Like so many guys my age, I need a little blue pill to increase my confidence which I explained to Sasha. She was fully accepting of this and pointed the way back to the car.

Once back at the motel, we both used the bathroom briefly to clean up, brush our teeth etc. I waited on one of the beds for Sasha to come out unsure as to whether to get undressed. This whole experience was something that hadn't happened to me in years. Sasha came out of the bathroom still wearing the same dress. I quickly removed it and confirmed that she wore no underwear of any kind. I just adored her at that moment. In part to wait for the magical blue pill to work, I turned Sasha face down on the bed and gave her a light massage along with little kisses starting at her neck. She was so accepting of my attention and reacted and moved to my every touch. Eventually I worked my way to her inner thighs and the reactions and movement increased exponentially. I avoided direct contact with her pussy for a long time until I just couldn't resist. Already there was a significant wet spot on the sheet. After a few light direct touches to her clit, I turned her over on her back and went down on her. After a just a few light licks, I think that she had a quick orgasm judging by the way she shuddered and was temporarily sensitive. However she allowed me to continue and I rhythmically applied my tongue to her enormous clit while inserting three fingers in her vagina. Her massive orgasm came suddenly. Her hands moved from casually tweaking her nipples to holding my head firmly against her pussy. Her breathing became very heavy and then the contractions started. At the moment, she held my head firmly and her body went completely stiff. I kept my fingers in her as she rode the climax but said very little. I looked up at her and our eyes briefly met and I knew she that was more than okay.

Once she came down she pulled me up to her and we kissed deeply while I resumed lightly touching her. She made a special show of licking her juices from my face. We talked and hugged and kissed for an unknown period of time until she was able to regain some of her strength and noticed that I was mildly humping her.

She slowly moved down to my penis and started gently sucking me. From her purse, she found a condom which she slipped into her mouth and then put it on me. She then slowly sat on me. Sasha was so warm and so wet. I have never experienced anything like that first moment of entry even with the condom. She sat up right for a while and watched my reactions to her movements. I motioned for her to help me sit up too and that clearly seemed to hit the right spot for Sasha as she really started grinding against me. It was clear that this was for both of us. In this position, I really felt her contractions when they started. I think she tried to suppress her orgasm until mine too started. Eventually, we could no longer maintain the upright position. We collapsed back on the bed laughing and breathing heavily and just feeling that wonderful after sex glow. We both slept like babies that night but on the other bed. The first one had a four foot wet spot!