My Morning Cherry

In a strictly physical carnal sense, I've always been a butt guy. Little butts, big butts, dimpled butts, bubble butts, all can be a turn on in their own way. There is the young professional at my office that has tight little butt that loves to wear tight slacks. There is the older woman at the grocery store that I can't help but bump into with her rare wide ass. There is my large neighbor with her flabby butt taking in some sun on her patio lounger. I am surrounded by butts that become fantasy. Fantasy for how I would knead them, fantasy for how I would be enveloped by them, fantasy for how I would kiss them, fantasy for how I would lick them. These fantasies, for years, have mostly remain just that. But that all changed several months ago due to a single fateful encounter during my commute, my butt awakening.

Cherry had a fitting name, that I never knew until this encounter. For months she was just Red. I had named her Red due to her long wavy Red hair that framed her round face wrapped by a pair of black framed librarian glasses. Cherry also liked to wear red lipstick that was a stark contrast to her pale complexion. Cherry was a large girl. While standing 5'9" tall gave her above average height, it was her large hips, huge but, and massive thighs that immediately drew me to her. Her small perky breasts that she seemed unconvinced to display would seem disproportionate to some, but to me, they only served to place the proper focus onto her well endowed Ass-ets.

Cherry would board the train 2 stops after mine, often at a time when the pods of 4 seats, 2 sets of 2 seats facing each other, would require a second person in each pod. I remember waiting in anticipation each day as to which seat she would choose. One day she would choose my pod, the next day she would choose another pod, there never seemed to be a pattern to her choices. The days she would choose my pod, I would get to see her thighs pressed against each other, her ass filling the bucket seat, and depending on her outfit, the outline of her belly resting over her lap. The best part was her squeezing in across from me as she was forced to turn her large backside to me when entering the pod. The highlight of my commute would be Cherry turning to sit down while squeezing past me, putting her round, gigantic ass right by my face before plopping into her seat. She wore a nice fruity perfume that while pleasant, I often wished was forgotten so I could get a soft whiff of her musk on the way to her window seat.

Cherry often listened to her headphones, or read a book, typical commuter entertainment options to bear the near hour-long train ride into the city. Sometimes she would snack too, and I use to fantasize about each bite of her breakfast adding another inch to her hips and thighs. One morning, after choosing my pod, she turned in to sit down, bringing me to the climax of my morning commute, when her purse slipped through her fingers onto the ground. I gasped and leapt forward to help her collect her items, accidently bumping her, but avoiding any lewd groping. I even got down on the ground to reach under the seat to find that illusive Carmex that went rolling across the aisle. This is when Red became Cherry, as she was most appreciative, she introduced herself. I did my best to smile and bask in her thankfulness. I was rewarded when Cherry became my regular pod mate in my morning commute. Each morning I was greeted with a smile from Cherry, and then a close-up view of Cherry's booty while she snuggled into her window seat.

My morning Cherry continued for several months, when one afternoon things changed for good. I was sick of work for the day and decided to take a 3 PM train home instead my usual 5 PM train. Having never seen Cherry on an afternoon commute, I was surprised after taking my seat to see Cherry climb the stairs and make eye contact with me from the aisle. I smiled thinking on my luck that my morning Cherry would also be my afternoon Cherry today, and Cherry obliged by walking right to my pod and taking her window seat. Drinking in another view of her curvy ass, Cherry then put her headphones on and I settled into a book, and 20 minutes later we were both interrupted by the conductor. A car accident on the tracks would stop the train indefinitely. A collective exasperated sigh was released from the passengers near me, and we settled in to an unknown delay.

Cherry had her headphones off and was looking clearly frustrated, so I took my opening.

"I wonder how long we will be delayed?" I muttered.

Cherry responded "I am so screwed, I am supposed to be at my second job behind the counter at a medical supply company."

This confirmed why I never saw afternoon Cherry before. She must leave early in the afternoon to a second job each day, robbing me of the view I was currently enjoying this afternoon. "I'm sure they won't mind if you are a few minutes late, they have to realize that you aren't in control of a train delay."

She furrowed her brow, "I need this job, I'm scraping by right now on rent and food, and if I lose this job, it's only going to get harder" and looked down despondent.

That's when I had my best thought of recent memory. "Let's jump off this train and share an Uber. I'd be happy to drop you off first on the way to my park and ride." She looked up, and smiled slightly, "No, I can't do that, we're 30 minutes away and I don't have the cash to split an Uber."

Shaking my head "No, it's no problem, I don't want to wait on this train for hours for this accident to get cleared up, and your work is on my way, my treat."

Trying to give her a reassuring smile that I wasn't a creep, at least an Uber driver would be behind the wheel, I saw her expression relent and she gave me a nod.

I of course said, "Ladies First" and enjoyed another backside view as we exited the train and made our way to the curb to await our ride.

After jumping into the backseat of the car and making it a few blocks away from the stalled train, we quickly realized that escaping the train would not escape the accident, and we grinded in traffic to a halt. The Uber driver said our 30-minute trip was going to be an hour, and we should settle in. Cherry looked distraught.

"Just call your employer and tell them the situation, what's the worst that can happen? Giving them notice is going to be better than just not showing up." I said. Cherry agreed and delivered the bad news, only to get a better response than apparently, she was expecting. They told her to take the night off, she could make up her shift on the weekend if she needed the money, and not to worry about compromising her job.

"They must be really nice people." I said.

"They are" Cherry responded. "They have loyal customers from the Chiropractor, Dental, Masseuse, and Nursing schools that are regular repeat customers for their custom medical tables."

"Masseuse schools? I wanted to be a masseuse a few years ago. I had a back injury and the Masseuse I worked with was so kind and gentle and helped me feel so much better that I almost went back to school. I even bought a massage table and tried to recreate some of his techniques with my family and friends."

"No way" Cherry stated. "You have some lucky family and friends. I know how expensive a massage can be so to have someone have a table and be willing to rub you down for free practice must have been great for them."

Shaking my head. "If only that were true. They refused my offer and now I have an expensive table sitting in my garage. I think they thought it was more intimate than appropriate, which I assured them was a laughable excuse." Chuckling. "I wasn't planning on molesting them."

Cherry laughed. "Fools! All of them!" And then we both noticed we were moving through traffic again. The Uber driver was still heading to Cherry's work address, but with her changed plans, I talked her into letting the driver drop her off at her apartment.

The next 15 minutes was wasted thinking of any excuse to create some physical contact. Touching her knee when I had something interest to say. Sliding into her when we went around a sharp corner. Accidentally bumping hands.

We finally reach her apartment building, and I am anticipating getting another view of her huge ass, when she surprised me. "You know, I have a massage table in my apartment that's never been used. I bought the thing at a steep discount thinking I could use it, or practice with it, or at a minimum sell it to make some money. My afternoon is now free, would you want to come up and get some practice?"

A genuine ear to ear smile erupts on my face. "Absolutely!" as I rush to open my car door before she changes her mind. I can't believe my good luck. This woman I have been fantasizing about is asking me to rub her down. Stealthily, I reach down to adjust my pants as I escort her to her entrance.

We arrive in her small apartment and she throws down her purse and bag and tells me to grab a glass water or a soda while she gets the table setup. I oblige and see her struggling to move the table into her leaving room. Lending a hand, we unfold the table and I suggest she change into something more casual as the formal pants and shirt she is wearing are going to be difficult to work around. I also ask her if she has any massage oil and surprisingly she does.

I'm putting a sheet on the table and taking off my collared shirt when I look up and gasp. Cherry is standing wrapped in a towel that barely goes halfway down her thighs. The towel barely has to stretch around small breasts but it's barely concealing her large milky thighs and an ass that must be 50" wide. Cherry jumps on to the table and lays flat on her belly with the towel covering up her backside from upper back to her mid thighs. Sensing this is my queue to get to work, I start rubbing some oil into my hands.

I ask if we can lower the towel a bit on her back, and she obliges, and surprisingly, as she lowers it down, I see that she has no bra on. I pinch myself as I can't believe my luck and tuck my erection into my pants before I ruin any of this.

I slowly make my way down her back, giving every crevice its due attention. I knead her shoulders, her upper arms, her neck. Each area soliciting a soft moan of enjoyment from Cherry. "Are you sure you're not a licensed Masseuse? This feels great. Your family are idiots." She says. "I doubt they would be as relaxed and as comfortable as you are. Just lay still and relax. Enjoy this."

I avoid her butt for now as I still don't know how far this will go and make my way to Cherry's feet. I use the oil to rub between each of her toes, gently caressing the sensitive arches of her feet. I move on to Cherry's calves, using two hands to apply pressure to the deepest tissue. I can see the goosebumps on Cherry's skin rise as I work my way up from her calves to the back of her knees. I am only inches away from her thighs when Cherry makes clear she has no intention of me stopping.

Cherry grabs the towel and pulls it up the top of her thighs, barely covering her huge ass. While her ass was barely covered, its clear she has no panties on as the towel does nothing to prevent me from seeing some hair creeping out from between thighs. I feel my penis jerk in my pants, as take a sip of cold water to slow down my arousal, as I begin to work up from the back of her knees.

I take my time rubbing both of her thighs individually. Reaching around with fingers, I use my thumbs to slowly knead up and down her thighs. The soft dimples in her thighs compress and retract as I snake my way up the back of her thighs towards the base of my fantasy. The ass cheeks I have been staring at for months only loosely covered by a towel.

I continue strangling each thigh with both hands moving higher and higher and Cherry furthers my gumption by spreading her legs further giving me unfettered access to her inner thigh. Her pussy is now almost on complete display as the towel is still doing its best to conceal her but. As I continue slowly working my way up each large thigh, hoping this moment lasts indefinitely, I can see beads of moisture on her pussy lips and her trimmed pubic hair. She is soaking wet.

While her pussy looks delicious, I am more interested in getting my hands on that ass, so I start my upwards near the base of her butt cheeks, bumping into the towel with each caress. I am deeply kneading the fold in her cheek trying to work my way to the large globes when Cherry reaches with her left hand and removes the towel completely. Her Ass was glorious. Dimpled near the base, fleshy in most parts, firm in others, it spreads out wide and is begging for my hands attention.

I rub each cheek, at first gently and with some oil, as a sign of how appreciative I am to this completely exposed view, and then firmer as I begin to knead each cheek with all the pressure she can handle. As I move to the inside area of each cheek, I make sure to gently graze Cherry's pussy and asshole. While I am hopeful with her wanton display of flesh that she is craving a happy ending, I am more interested in just how much ass play Cherry is going to put on the menu.

I continue to gently tease Cherry's pussy and anus, by grazing my thumbs near these most sensitive areas. Cherry responds by slightly raising her hips to each graze. I reach over to couch and grab a small pillow with my left hand while continuing to massage her but with my right, when she raises her thighs again and gently insert the pillow under waist. Her soft moans has me on my edge as I push forward with my perversions.

I gently apply pressure to Cherry's clitoris with the base of my thumb, making slow circles and blowing a little bit of air with my mouth. I want Cherry to feel my breath on her pussy and beg to have my tongue lap at her most sensitive areas. I lower my mouth right above her pussy, gently blowing on her while continuing to massage her ass with one hand and her clitoris with my other. I stick my tongue out and instead of looking her pussy, I gently apply pressure right on her anus. Cherry moans loudly pushing her hips back in force as I continue slowly rimming her.

Continuing to rub her clit with my thumb, I stick my tongue out and insert it into her rosebud to her squealing delight. Cherry continues to aggressively push back in my face as lather her anus with my tongue and saliva, taking in all her scents, all her flavors. My pants at this point can barely contain my erection as a wet spot forms on the front of my trousers.

After shaking in pleasure with my tongue up her ass and my thumb rubbing her clit, Cherry moans and says "Fuck me" and I need no further invitation. I jump on top of the massage table and penetrate her pussy from behind. I'm so turned on, my penis can feel everything and as I plunge into Cherry over a second round of moaning and shaking. Sweating and thrusting, I unload inside her with one last exhaustive push.

I collapse next to Cherry, barely catching my breath, as she continues to lay face down on the massage table. I begin to clean up and put my clothes back on and thank her for the practice. Cherry looks at me and smiles and without saying word, closes her eyes. I finish putting on my clothes, and notice Cherry is now asleep, so I slowly sneak out of her apartment and make my way to the street and eventually home.

The next day, I start my commute like any other, eagerly anticipating my morning Cherry after what had happened the night before. But Cherry did not show up. Cherry failed to show the rest of the week, and the rest of the next week and I thought my luck with Cherry had finally run out. Then, the third week after our tryst, another commuter approached me in the morning at Cherry's stop and handed me a letter, saying a red-headed woman gave her the letter and asked that she deliver it to a Man matching my description. I smiled and thanked her.

I opened the letter.

My dearest Masseuse. I still shiver thinking back to our rendezvous several weeks back. I've never had a guy lick my ass before, and never knew how pleasurable a massage could be. I did not tell you over the months on the train that I was engaged to be married. I don't know why I kept coming to sit next to you on the train, maybe it was how I noticed in the reflection in the window as I was sitting down how much you enjoyed staring at my ass. When you told me you wanted to be a masseuse, I was imagining how much attention you would give my butt, so I decided to be naughty and go naked under my towel, but I don't think I was anticipating what happened. You made me feel so desirable and sexy and gave me a climax I will always remember. If you ever open a massage school, I'll be sure to refer my fiancé to you for training.

Xoxo

Cherry