Traveling with Sherry

Mar 22, 2024 // By:analsex // No Comment

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Sherry was a 35 year old, attractive, blonde, divorced mother of two, who had been working at the same company as me for several years. Since we were first introduced during a business trip, her natural and effortless good looks always seemed to catch my eye. She had natural blonde hair which she only accentuated with a hint of additional color, and was one of those women whose view on make-up was a ‘less-is-more’ approach. She was not overweight by any means, but had enough of a physique to demonstrate that she did not spend hours every Saturday morning with the other divorcee’s at the local aerobics class. She didn’t bother with exceptionally short skirts or lengthy high-heels, but dressed elegantly enough to demonstrate that she cared about how she looked. And she pulled this off very well.

Eventually, Sherry and I started having to work together more often and over time developed a nice working friendship. Ours was one of those office relationships that would on occasion generate an after-hours drink at a local bar to gripe about co-workers or local management, but initially never got beyond the occasional flirtation. Ironically, we were both from the same home town, over 400 miles from where we now worked, so it was often easy for us to migrate toward each other. During the initial months of us working together, I was in the early stages of a relationship, and though she often expressed not being very happy, Sherry was also exploring a new relationship, her first since her divorce. It was one of those things that while I think we both found each other attractive, we both knew we were seeing other people and so we

never took each other’s flirtation very seriously.

After working on and off together for nearly a year, a business trip to the coast and several glasses of wine at a sea-side bar, changed the way we would look at our relationship. We had shared a glass of wine or a cocktail while traveling several times before, but this was one of those nights where you knew by the conversation that something was different. Sherry expressed with more emphasis than normal that the relationship she was in was not one she wanted long term, and she was afraid that it was just something she jumped into on the rebound from her marriage. And while I knew my relationship wasn’t going to be long term either, I found myself reciprocating with her feelings more than normal.

After having our drinks, Sherry said she wanted to go for a walk on the beach before we had to go back to the hotel. I said that sounded like a nice idea and agreed to go, although with some apprehension. And though I was reserved, I also had that feeling of excitement in not really knowing what might happen. After a long walk up the beach, Sherry said she wanted to sit down for a few minutes and take in the sound of the ocean and the reflection of the moon on the waves. Within fifteen minutes of us sitting down in the sand, we shared our first kiss. It really wasn’t her, or me for that matter as far as who took the lead, it was one of those things that just happened. Once we got back to the hotel, I escorted her to her room honestly thinking that we would possibly kiss goodnight, allow the alcohol to leave our system, and sleep on the events that happened that evening. Those of you who have shared similar experiences know however, that sometimes when things start going a certain way, it’s almost impossible to stop them. I left Sherry’s room a couple hours later, a bit less inebriated but certainly spent. I went to my room and showered, then climbed into bed with a head full of swirling thoughts of the sex we just had.

Since that interaction, Sherry and I remained friends, but for whatever reason never explored our feelings any further. We had several conversations over drinks about what happened, about the sex being great, and whether we should pursue things, but it just never really happened. I think we were both more concerned about our careers and about what our co-workers would think, and time slowly went by with what happened that night slipping into the recesses of our minds. Before too long, we were back into the same occasional flirtatious working relationship that we had before the night we slept together.

As I mentioned, Sherry and I were from the same hometown, and as such, were both fans of that city’s professional football team. Often during our travels, the conversation would ultimately switch to how or what “our” team was doing. This was something else that helped with the camaraderie and friendship that we shared. It was just easy for us to be around each other. Little did we know then, it would be our shared affection for that football team that would be the cause of our next encounter.

Approximately a year after Sherry and I had our Escort sexual fling, I was planning a trip to my home town for the opening day of football season. This was a trip that my brother and I tried to make every year. A month before the game would happen, I would have the tickets purchased, the hotel booked, and would have scheduled the necessary time away from work. Two days before my brother and I were scheduled to leave however, he had a problem come up at work and reluctantly called to say he would not be able to make the trip. I spent the next day frantically calling all of my buddies to see if anyone could make the trip with me. I’m sure I could have sold the tickets online, cancelled the hotel reservation and just skipped it, but I really wanted to go back home.

I was actually at work the following day when I got an online chat from Sherry asking me about some work related research we had conducted a few weeks earlier. It was really strange, as soon as I saw her name pop up on my computer, it hit me…why not ask Sherry? My online response back to her addressed the work request first, then I asked if she would be watching the game that weekend. Of course her reply was instant, “You know it!” I simply replied with, “How would you like to watch it in person?” My chat indicator sat silent for a few minutes then pulsed to life, “Why do you ask?” Sherry replied.

I spent the next ten minutes explaining my plight with my brother, the fact that I had two tickets ready to go, hotel reservations, but no one to go with. She was reluctant at first, but with some prodding, she told me she would check that night to see if her “Ex” would watch the kids for the weekend. The next morning I arrived to work and after booting up my computer, I had an email waiting in my inbox from Sherry stating that she could go. She ended the email however with the following disclaimer, “I’m excited to go to the game, but understand we’re going just as friends…right?” My reply was simple, “Of course!”

The following morning, Sandy and I began the four hundred mile drive to our home town. I thought the drive might eventually turn awkward, but the comfort we had around each other kept that from happening. We talked about work, personal stuff, and of course what we planned to do while back home for the weekend. By mid-afternoon, we were pulling into the parking deck of one of the downtown hotels.

The football game was not until the following day, and until this point, neither of us really approached the details of what protocol we would follow in sharing a room. As we approached the front desk at the hotel, I finally broached the subject, “You know, we could get separate rooms if you would feel more comfortable.”

After a brief pause Sherry replied, “That’s ok, I’m sure the rates are crazy for this weekend, and besides, we’ve already agreed we’re here as friends.” She tilted her head and looked at me as if that was a question.

I nodded, “right.”

As we waited our turn in line to check in, Sherry turned to me and said with a slight chuckle, “But you did say there are two beds in the room right?”

I let out a soft laugh and joked, “No, just one…a king size water bed…and a Jacuzzi tub.” She let out a laugh of her own before I set her mind at ease, “Just kidding, yes two double beds.” After several minutes, we were checked in and headed to our room. Once unpacked, we each spent time taking a shower and then headed out to grab a bite to eat. It was a seasonably warm fall night and we were able to walk around the downtown area stopping into several pubs and local bars. We found a neighborhood pub where a guitar player whaled out the blues and we hunkered down for several hours listening to the music, talking and drinking beer. Just after midnight, we were both tired as well as a little light headed and agreed it was probably time to head back to the hotel.

Riding up in the elevator, Sherry said she would wash her face, brush her teeth, then while I was in the bathroom, finish getting ready and slip into bed. She let out a small laugh when she said I wasn’t allowed out of the bathroom until she said the coast was clear. We were not in the room fifteen minutes before we were both in our respective beds and under the covers. I was in the bed closest to the wall with Sherry in the one near the window and the floor-model air-conditioner.

I noticed after turning out the light that neither Sherry nor I remembered to pull the curtains completely closed, and a seam of light from the city outside made its way across her bed and created a soft glow on that side of the room. As I lay there I could not help but realize that with my bed tucked against the wall, I was in relative darkness. Sherry on the other hand, while not completely distinguishable, in that I could not make out any expression on her face, I could however completely make out the outline of her body and see her arms on top of the covers.

After a minute or two we began chatting softly, talking about the drive, the music we heard earlier, what we would do tomorrow, just pillow talk before falling asleep. Then we stopped and we were both laying there in silence. After only a brief moment, I heard what sounded like soft pounding on the wall next door. I perked my ears and listened harder, now hearing faint but audible moans. Over the next several minutes the pounding got faster and louder, matching the moans of the woman who was obviously enjoying what she was doing. In unison, Sherry and I busted out laughing, “Sounds like she’s having fun,” I said. “Who needs Skinamax?” We both laughed harder. It was not long before we both heard a high-pitched shrill from the women next door indicating the unmistakable sound of her orgasm. And just like that, the wall pounding stopped.

Still smiling, I rolled over turning toward Sherry and got ready to fall asleep, assuming she was doing the same. We were both quiet for about fifteen minutes when I opened my eyes and noticed Sherry had pushed her covers down to her waist. I blinked my eyes rapidly trying to focus and could see that she was not naked; she had a spaghetti-strap top that effectively covered her breasts and came down just below her belly-button. Because of the darkness of the room, I believed that she had no idea I could make out a clear outline of her body from the light coming through the window. I did assume however that since no light made it to where my bed was located, that she would have a harder time making out my side of the room. I lay there for a moment thinking she was asleep, and then watched as she lifted a hand and slowly circled the outside of one of her nipples.

Sherry’s head was turned slightly away from me and I watched as her index finger moved around her nipple in slow, gentle circles, until I could see it become erect in the shadows. For a second I had to strain to think if I actually saw that happen, thinking maybe it was just my imagination. Then I saw her other hand slowly maneuver below the blanket down toward her waist. I could see the covers directly above her hidden hand begin to move back and forth. In a moment, the hand that was exciting her nipple slid beneath her top and her fingers disappeared around her breast. I could see from the glare of light that she was squeezing her tit and pinching the tip of her nipple.

I felt a pulse of excitement between my legs as my cock twitched to attention. In as slow and quiet a move as possible, I began to roll softly onto my back. I was holding my breath, and once in position, I had to concentrate to not let her hear my breathing. Though I was on my back, I kept my head turned to where I could still see Sherry, basked in the glow of the window. I watched as she removed her hand from around her breast and slid both straps of her top down off of her shoulders. In the muted light, I had no trouble making out both of her breasts as they came free from her top. I could see that each of her nipples were hard, and she went about squeezing her breasts before using her index finger to gently caress her nipples. I was growing more excited by the second and reached down to feel my steadily growing shaft through my boxers.

After a minute of watching Sherry please herself, I carefully slid my hand between the slit in material on the front of my shorts and pulled my now rigid cock free. I felt a surge of arousal as I wrapped my fingers around the head and gave a firm squeeze. With my other hand I slowly raised the covers slightly to allow several easy strokes of my warming cock. In the dark I savored the sensation of feeling the soft skin, the texture of the veins and the velvet like lip of the head. I took my index finger and carefully massaged across the tip searching for any pre-cum that would soon emerge. I continued stroking myself with a slow up and down rhythm.

I could see from Sherry’s chest that her breathing was increasing and as quiet as she could, she slowly pushed the covers down to just below her hips. I was surprised that she had no underwear on. Even in the dark I could make out the small mound of hair that covered the top of her pussy. My arousal continued as I took in her body from head to toe, her head still turned toward the window, her breasts bare, her top pushed down covering her stomach, and the sensual dark patch over her pussy. With a hand still holding one of her breasts, she began using the other to massage the top of her clit. I could see her as she kept one finger steady at the top of her pussy while using another to circle and explore the folds of her lips. Occasionally I could see her lift her waist slightly, pushing toward her hand and fingers when they would reach the right spot. The excitement for me as I watched Sherry pleasing herself was incredible. Both of my hands remained under the covers, one slowly increasing the speed with which I was stroking my shaft.

Excitement raced through my body as I pulled, swirled and stroked my cock. I slipped my other hand under the waistband of my boxers and cupped my balls feeling them tighten. Sherry was comfortable with her one hand simply holding and occasionally squeezing her breast and I pictured her holding it that way for my lips. I imagined the feeling of her firm nipple, sucking and licking while she would squeeze and loosen her grip. It wasn’t hard for me to recall her sounds of excitement. I brought my mind back to what was in front of me, and the feeling of us both masturbating in the same room with each other, but trying intensely to not be discovered was an amazing thrill. I had to concentrate on the noise of my breathing as my pulse continued to quicken. It was then I heard the soft lapping of moisture coming from beneath the fingers Sherry was using to explore her slit. She must have been conscious of the sounds for as soon as she would hear her wetness, she would stop and reposition her fingers and move them with a different motion. Like the stroking of my cock, the circles she was drawing across her clit increased in speed and intensity.

I was not satisfied working my cock from the slit in my boxers so I slowly lowered my own covers inch by inch until they were now down below my waist. The process seemed to take forever, but soon I had my boxers lowered to where I could have freer movement to my cock and balls. I gently tickled myself at the base of my sack and imagined the sensation of my finger as Sherry’s tongue. In an instant a similar wet sound that I heard earlier from Sherry was now coming from inside my cock. My cum had filled my shaft and was waiting for me to reach the moment of release.

Sherry was trying hard to be silent, but I could hear the soft moans of her climaxing as she lifted her chest and rapidly increased the pace of her fingers. After a brief moment, she lowered her back flat to the mattress and removed her fingers from her moist clit. I could see her chest heaving with the excitement of her orgasm.

My cock was pounding as I stroked as hard yet as quiet as I could manage. Across from me Sherry lay motionless, and then brought up the hand that had just completed its task and used a moist finger to circle one of her nipples. I opened my legs as much as possible and looked down at myself in the dark, holding my cock straight up in front of me, my hand firmly around its base. While it was completely dark on my side of the room, my eyes had adjusted enough for me to clearly see the outline of my hand holding my exposed cock. I was close. I took a quick glance back to Sherry to make sure she hadn’t moved or possibly looking in my direction, then turned back towards my shaft in the darkness.

I stroked and twisted my hand around my throbbing cock, replaying the sight and sounds of Sherry squeezing her tits, massaging her clit and the lips of her pussy, climaxing only a few feet away from me. I felt the unmistakable sensation and pleasure of my oncoming orgasm. As my toes tightened, I held my breath and gave my cock two more targeted strokes. I wrapped my hand firmly around the base as the first stream of warm cum erupted from the head of my cock. I felt cum splatter onto my cheek and down my face. I turned my head to avoid getting cum in my eyes as I awaited the remaining pulses from my shaft. As hard as I tried, I couldn’t help but let out a muffled groan of my own as several more pulsing ropes of cum left my cock and landed on my chest and stomach. I slowed the stroking of my cock and felt warm droplets of cum roll down the side of my neck and waist.

I quietly calmed my breathing before focusing now on the fact that I had cum everywhere. I decided I would wait until I had savored the feeling of such a wonderful orgasm, then slip into the bathroom to wash up. I took a final deep breath readying myself to head to the bathroom when the sound of Sherry clearing her throat broke the silence, “mmm, I smell you,” she said softly. I could definitely smell the indistinguishable aroma of my cum, but hoped that it was just because my powerful ejaculation had landed on my face and neck. The reality was that I had come so much, there was no doubt that the smell now filled the room.

Her comment took me by such surprise that I was at a loss for what to say. Do I come clean? Do I pretend to be sleeping? Do I joke it off? After a moment or two, I finally stammered out the only thing I could think to say, “Guilty as charged Sherry…that was incredible.”

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