Trysts on a Train
by Tarl Cabot
Copyright© 2023 by Tarl Cabot
Erotica Sex Story: Mike has some unexpected sexual encounters while traveling cross-country by train.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Ma/Ma Consensual Gay BiSexual Heterosexual TransGender Fiction Sharing Group Sex Anal Sex First Masturbation Oral Sex Public Sex .
Spend eight months or so traveling New York State, from County to County and you’ll pray for some relaxation time. I did. I had to update voting machines all over New York with new software to insure the security of your votes.
Once the election was over and I secured the machines it was time to go home. I mean back to California. I packed up my belongings and sent them ahead via PODS. It would take about two weeks to get everything back there.
No, I could have hoped on a plane the next morning and been there for dinner. But no, I wanted my relaxation time. So I booked a five-day train tour from New York to Los Angeles. A private room and access to a glass-top viewing car were just what I needed.
I left Penn Station in Manhattan on the first leg of the trip. The only accommodations were coach seats. But they were bearable. I would transfer to the Coach-liner at Chicago’s Union Station. There I would get settled into my private room.
It was kind of nice getting senior discounts now. I never would have paid full price for this twenty-three hundred mile journey. But with discounts in place, I boarded the train at Chicago’s Union Station and we pulled out, headed for the west coast.
Since the train was nearly empty I was able to get what amounted to a double room. That meant I could lay down for a nap without having to fold up my laptop and table to fold down the bed. After settling in I went to the lounge car to get a drink and head to observation.
I was alone on the upper deck watching the Cityscape fade to farmland. Rolling fields of wheat and corn blurred past. They did seem to wave. I was nearly finished with my first beer of the week when a young woman walked through and sat at the far end.
After maybe an hour the overhead speakers announced lunch being served in the dining car. I got up and headed down for some lunch. I ordered a Monte Cristo sandwich, a sweet iced tea, and a chocolate mousse for dessert.
While waiting for the food to arrive the same young woman from the observation deck approached me.
“Excuse me,” she said politely. “It seems it is just you and I for lunch. Would you mind if I joined you?” I motioned to the empty chair across from myself and she sat down. She was dressed in older hippy-style clothes. Painted bell bottoms, a tie-dyed t-shirt, and a floral scarf around her head.
We talked about nothing in particular. I’d comment on the scenery and she’d tell me her thoughts on nature and sustainable crops. She introduced herself as Charlotte.
“Nice to meet you Charlotte,” I extended a hand across the table. “I’m Mike.” Then I grinned, “But my Mother and enemies call me Charles.” then I winked.
“Well Mike, it’s a pleasure to dine with you,” she replied with a winning smile. After lunch, we walked back toward the observation car together. Somewhere between Des Moines and Omaha, the train got crowded. I told Charlotte I was headed back to my room.
At her disappointed expression, I told her I wasn’t good with crowds and needed to decompress. I promised to look for her around dinner time if the crowds had subsided by then. Charlotte gave me a tight smile and wished me a comfortable rest. I retired to my room and shut the shade.
When I awoke, it was darker than I’d expected. I raised the shade and found it was dark outside. Checking the GPS on my phone, I found we were now halfway to Denver out of Omaha. I freshened up a bit and went to the dining car. Finding it closed, I went up to the observation deck.
There I found Charlotte sitting staring out into the darkness. There were streaks of lights we passed and the glow from the train’s lights illuminated the area for a few feet to each side of the rain.
“I wasn’t sure how long you’d sleep, so I got you a special and a bottle of beer,” Charlotte said without turning toward me. On the table next to her, sat a plate with some veggies, a lump of mashed potatoes, and a Salisbury steak in some kind of demi-glace. A long-neck lager sat next to the plate.
“Thank you,” I said in a low voice. “I must have been more tired than I thought.” She turned and smiled at me as I unwrapped the plate and began to eat the lukewarm meal. The beer though was still cold.
“The night is very calming, isn’t it?” she asked me and nobody simultaneously. “It’s quite freeing.” That was when she pulled her t-shirt up over her head and flung it to the floor. She wasn’t wearing a bra. I could see the definition of her back as she raised her arms to the ceiling.
The smooth lines of the muscles in her back seem to make her equally smooth skin ripple in the changing lights from in and out of the train. I must have gasped involuntarily because she turned to face me. I felt my jaw go slack as I silently mouthed “Oh My.”
Charlotte appeared to be a woman in her early forties. Now exposed fully to the waist, she was in amazing shape. Her long chestnut hair now flowed down her back and rested just below the waist of her jeans.
Her breasts were large but still very firm. Her areolas were small and her nipples were like hard eraser tips. She’d either never been pregnant, or never lactated. Her abdomen was tight and defined.
Charlotte smiled at me. She seemed amused by my discomfort. She walked over and stood face to chest with me as I sat at the small table. “Does my nakedness disturb you my son?” she asked.
What? My Son? What was she saying? Was she fucking with me? I shoved my chair back against the train wall and stood up. “Look, it isn’t so much that it disturbs me,” I began and walked around her and went to pick up her shirt. “It’s just a bit inappropriate, don’t you think?”
“How so?” Charlotte asked. “There is no one here but you and I,” she stated confidently.
“True enough,” I answered. “However this train is not yours or mine and it is technically a public forum.” I handed her shirt to her. “Anyone could walk in at any time. We are not alone on this train.”
Charlotte put her shirt back on and looked at me questioningly. “What if we were in private?”
The question was a fair one, so I answered honestly. “You’re a gorgeous woman,” I admitted to her. “I’m old enough to be your father. But yes, if we were in private I wouldn’t have reacted like this.”
Charlotte smiled and grabbed my hand. She pulled me along toward my room in the sleeping car. I’ll admit, she was conscious of my cane and limited ability to move fast, so it took a few minutes. Once we were standing outside my room she asked to come in.
“Will you invite me in?” she asked. There was no cute pout or other sign she was trying to influence my decision. My confused look made her elaborate. “I’ll answer anything once we’re inside.” then she asked again. “Will you invite me in?” I just nodded dumbly and opened the door.
I walked around the bed that I intentionally left open for my convenience and sat in the lounger next to the window. I reached down and grabbed complimentary water from the mini fridge and offered one to Charlotte.
She declined but sat down on the edge of the bed. I took a sip and asked the big question. “Ok so what the fuck is going on?” she seemed shocked for a brief moment, then composed herself. “If you’re looking for a place to start,” I added. “The beginning is the best place.
Charlotte just smiled at that and began. “Well.” she paused and sighed after that. “I’m a Nun. Or at least I used to be.” The lack of reaction from me seemed to upset her a little. “You are not a Church goer?” After her initial display, I thought I’d shock her.
“Moses is my savior, sister.” her sideways look made me smile. “My Ima says I’m a good Jewish boy and should look for a good Jewish girl.” I Mikeled under my breath. “But she’s passed on now.” Charlotte crossed herself. Probably more out of habit than real concern for my dead mother.
“I am sorry for your loss.” she offered and I just nodded. Taking a deep breath she continued. “I was forced to join the convent when I was a young girl by my mother.” with her hands on her thighs, she began scratching her jeans with her fingers.
“The first few years were my hell. I tried to run away several times.” She went on to tell me about how she eventually became desensitized and simply accepted that she was stuck there. Until a few months ago.
“I don’t know what came over me. I just snapped,” she admitted. “I’ve told many people over the years that confession was good for their souls. So here is mine.” Charlotte sat up straight and looked me in the eyes.
“I Stole a bottle of Sacramental wine and got drunk in my room.” Then I saw her blush. “Then the Mother Superior caught me Masturbating. She was searching all the rooms for the wine.” One of my eyebrows shot up at that, and she glared at me indignantly.
I held up my hands in a gesture of surrender and Charlotte took a deep breath and went on. “I suppose you could guess what happened next.” She spread her arms and motioned down her body. “They’d destroyed my street clothes years ago to stop me from running away.”
She looked defeated as she continued. “These were what fit me in the lost and found.” she sighed.
I smiled at her and said, “First, I wasn’t judging you. Honestly, being the dirty old man I am, I imagined a bad eighties porn movie with Nuns in leather wimples and sprayed-on latex stockings pleasuring each other.”
The sudden look of astonishment on her face was highlighted by the bright red of her cheeks. “I may be considered a heathen by the church, but I still do have a sense of social propriety.” I extended my hands and motioned upward.
“We’re in private now if you wanted to unburden your breasts,” I said with a slight Mikele. “They are pretty magnificent if I do say so myself.” That just made her blush deepen, but wasn’t enough to stop her from repeating her performance from earlier.
She gave me a questioning look that demanded I give her my opinion. I told her once more that I thought her breasts were magnificent. She straddled my lap, facing me, and allowed me to fondle her breasts.
Her skin was warm and smooth. I cupped her large tits and ran my hands under them. The weight felt wonderfully hefty. I moved to run my fingers around her nipples and couldn’t help pinching, hard. This caused her to draw in a sharp breath but she hung her head back and closed her eyes.
“I haven’t been touched by a man like this before,” she admitted. “My boyfriend in junior high was clumsy and inexperienced. Then I was sent away.” The last word was drawn out with a deep sigh.
Feeling that this was probably going to continue, I decided to move ahead, and leaned in, taking one of her nipples in my mouth I clamped my teeth down on her soft skin, but didn’t bite down. I flicked my tongue over her hard nipple then swirled my tongue around it.
Charlotte began moaning and her hips began to wiggle and writhe on my lap. She wrapped her arms around my head and held me tight to her breast. I pushed back hard for a moment then switched breasts. I used my lips as suction cups this time and latched onto her like a baby breastfeeding.
Her back stiffened and her hips shot forward as I suckled her tit. If she had ever lactated I was sure I would have drawn something. But alas, nothing came. That didn’t stop me though. The rest of Charlotte’s body was responding to the stimulation.
A few minutes later, Charlotte began to make pitiful mewling sounds, and I realized that the thigh she was straddling was getting wet. The hot liquid was soaking my pant leg. She was cumming all over me. I pulled back and planted my face between her breasts and used my tongue to draw a wet line up her chest to her chin.
Charlotte shivered and looked at me, but her eyes shut tight as my mouth found hers and I locked our mouths together and began sucking on her tongue. Her back arched and her hips bucked again and more hot wetness bathed my leg.
I explored her mouth for a good five minutes before releasing her. I smiled, gazing at her lovely face. Then I slid the window next to me open. The cold night air blasted in and she shrieked as her chest was washed over with icy winds. Her nipples became hard again and I swore I saw them pulse.
A moment later I slid the window closed and kissed her on the cheek. Charlotte stood up and turned away. Holding her face in her hands she began to weep. I stood up behind her and placed my hands on her shoulders. She stiffened but kept crying.
“Tell me what’s wrong,” I whispered. “Did I hurt you?”
Charlotte sniffled. “No ... but,” she coughed and sniffed. “I lost control and did something dirty to you,” she announced. It was a good thing I was behind her and she couldn’t see the wide grin on my face and the fact I was holding back a laugh.
I grunted and coughed. Then asked, “What were you called in your order?” She stiffened and cleared her throat. Probably a sore subject now, But I had my reasons.
“I was Sister Mary Dymphna,” she stated with some pride, but I could hear a touch of disgust in it.
I spun her to face me. My smile was wide and I looked her in the eyes. “Well Sister Mary Dymphna, what you did was release your passion all over me and show me that you approved of my ministrations.”
She gaped at me for a moment with wide searching eyes. So I explained. “I’m not sure what you think you did. But what you did was have an Orgasm.” Her expression turned from questioning to perplexed. “You’ve never had one? Even with your clumsy boyfriend? Or when you Masturbated?”
That got me a stern glare, and she raised a fist at me. But just as quick as she’d gotten angry, she calmed. “Not like that. No,” she admitted. “Was that really what that was? I think I may have peed some.”
I couldn’t hold it in anymore and I laughed out loud. Hugging her to me tightly to keep from being struck by her wrath. “It happens,” I assured her. “It’s nothing to be ashamed or worried about.”
“But I thought that only happened,” then she stuttered and pointed down. “When a Man and Woman,” She looked pretty with red cheeks framed by her straw-colored locks. “When he inserts himself into her?”
“That’s one way.” I agreed. “But not the only way. Stimulation from all over your body can have that effect.” I ran my hand through her hair and smiled at her kindly. Suddenly she began kicking out a leg and bouncing around.
“This is uncomfortable!” she exclaimed. I nodded and skirted the bed and went to my closet. I pulled out one of my t-shirts and tossed it to her. “Go ahead and strip, wear that.” To her credit, she didn’t balk or act like a shy little girl. She stripped down totally and slipped the shirt on.
My Tee was large enough on her to be a dress. I found her staring as I stripped. I picked up a package of sanitary wipes, took a few, and tossed the rest to her. She caught it but continued to stare. “Clean up,” I said, and she was broken out of her reverie.
Had she been staring at my cock? I wiped down my thigh and tossed the used wipe into the toilet. I pulled up my sweatpants and threw on another Tee.
“We can wash those things in the shower later on,” I told her. “They can be hung to dry afterward.” Charlotte smiled at me and nodded. It was about midnight now. We’d probably be pulling into Denver sometime in the next few hours, but I wasn’t tired. Charlotte didn’t seem to be either.
I suggested we go get a drink in the lounge car before the last call. She questioned my suggestion, saying she was naked under the Tee. I pointed out that she was naked under her jeans and Tee previously and that my Tee was nearly knee-length on her. I tossed her my extra belt to wrap around her waist.
With the Tee belted, the sleeves rolled up and her cross trainers, she looked like she was wearing a summer dress with sneakers. I wore sweats and a hoodie. Then we exited my room and headed to the lounge.
On the way, I questioned her about her arrangements on the train. I hadn’t considered it until now. She told me she’d spent most of her money just buying a coach seat for the trip. I nodded and suggested we might want to sit there with our drinks, just to make sure they knew she was still on board.
While we waited for our drinks, I surprised Charlotte by asking a wandering conductor if I could move her from her seat into my Double Room. He told me it was mine, paid for until the end of my trip. I could do what I wanted since it was a double, but be sure she kept her boarding pass with her.
That settled, we found her seat, grabbed her backpack from the overhead, and headed back to my room. Once there we talked a bit more about what had happened and how I enjoyed it as much as she had. She told me stories about what some sisters used to get up to.
When I looked shocked she slapped my shoulder playfully, told me I had a dirty mind, and assured me they never put anything inside of themselves. I assured her that it made no difference to me, even if it did to her order. The conversation eventually devolved and she asked if I was going to do it to her.
I assumed she wanted to know if I was going to fuck her. So I asked. “Do you want me to have sexual intercourse with you?” she nodded somewhat meekly. “You sure?” I asked in a teasing manner. “I’m a broken old man. Probably no good for you.” then I winked.
She told me I was too modest, and I was a very comely man, and that the way I made her cum was impressive. The word cum didn’t sit right in my ears when she spoke it. At least not now that I knew she was an ex-nun. But it was cute nonetheless.
She also noted that she was intrigued by my manhood and what it would like and feel like when turgid. So she was checking out my cock, and wanted to see and feel it when it was hard. I wondered if I could get this nun to be vulgar.
I assured her there would be time before we disembarked. No need to rush. We lay down next to each other on the bed and slept. Just slept. Though I did have to work hard not to grab her in my sleep. We had been stopped in Denver for about an hour by the time the two of us awoke.
The layover in Denver for new passengers was only going to be another hour before the train would depart on the next leg of the trip. There was a plethora of shops and food establishments inside and outside the station. We shopped for some drinks and snacks.
After re-boarding the train we settled into my room again. Our next layover would be the following day in Salt Lake City Utah. For some perverse reason, I looked forward to it.
My eyes were forced open as the light came streaming into the room. I’d left the shade up last night. I sat up, yawned, and moved to sit in the seat next to the window. I was going to need lots of coffee. Charlotte rolled over and sat up a few minutes after me.
Somewhere in the last four or five hours, she’d shucked off the T-shirt I’d given her. She stretched languidly exposing herself to me in a rather erotic manner to my eyes. She caught me staring and smiled. How long had it been since I woke up next to a woman? Any woman?
“Good morning Mike,” she said lazily as she yawned and stretched in another Playboy-style pose. “Did you sleep well?”
“I did, thank you,” I replied with a smile. She stood up and stretched once more, this time exposing the full grandeur of her naked form to me, before turning to the bathroom and closing the door. I grabbed a fresh pair of pants from my bag, and a clean shirt.
When Charlotte exited the head she was carrying her jeans and Tee. I moved around to use the facilities and dressed after her. When I emerged she was dressed as she had been when we met. I smiled and motioned to her to follow me.
We walked to the dining car. Breakfast was in full swing, but there were only about six people in the dining car. We took a table away from others and began filling out our order cards. Charlotte hesitated for a moment then looked at me.
“It’s fine,” I said, waving my hand over the menu. “I hate having people watching me eat and not eating themselves.” I gave her a crooked grin. “Makes me feel guilty. So eat something.”
She smiled and began marking her menu card. She ordered the buttermilk pancake trio, and I got scrambled eggs with bacon and toast. I ordered coffee for us both.
The coffee arrived first and I downed my first cup black in a matter of seconds. The scalding liquid burned and woke me up instantly and I ordered another cup. “Ah, the nectar of the Gods!” I proclaimed. Charlotte giggled and sipped her brew.
“All food is given to us by Him,” she said as she lazily stirred her coffee between sips.
“And I gladly and enthusiastically accept what He has proffered.” When my next cup arrived, I emptied a packet of Stevia into it and stirred. “A little sweetness to offset the bitter awakening.” then I held up my mug in a toast.
After last night Charlotte seemed to be getting more comfortable around me. She also seemed less burdened, and more relaxed in general. She said grace quickly and then looked at me. I smiled and exaggeratedly said a Hebrew blessing over the food.
“BA-RUCH A-TAH A-DO-NOI ELO-HAI-NU ME-LECH HA-O-LAM,” then added a few other terms for some foods. Smiled and said, “Let’s eat.”
We’d end up in Salt Lake City late that night, with a whistle-stop halfway there in Grand Junction. Charlotte and I spent a lot of time in the observation car talking and watching the countryside go by.
I learned quite a bit about her time before the convent and while she was there. I learned that her parents had passed some time ago and she was headed to San Francisco to stay with her younger sister.
The talk eventually devolved into questions from her about sex. She’d explained her experience before the order and how she’d been finger-banged by clumsy a few times. The last resulted in her bleeding and it scared her.
I told her that he’d probably broken her hymen and it wasn’t any kind of major injury. I was somewhat relieved to know that if I was going to have her, I wouldn’t have the burden of taking that from her.
She brought up having seen me and that it looked kind of large. She was concerned it might hurt or wouldn’t fit at all. I’m not that big. About average if you ask me. Only about six and a half inches when hard and only an inch or so thick.
“It may hurt some,” I mentioned. “Only because you haven’t had that kind of penetration before.” I made a spreading motion with my thumb and forefingers. “But you will stretch. A woman’s body is made to accommodate it.”
We made a stop in Grand Junction around dinner time. The meal was average and we ate mostly in silence. Afterward, over drinks, Charlotte brought up sex again.
“Will you have sex with me tonight?” she asked. I can’t say I was stunned. With how she reacted to having her breasts sucked, I thought I wanted to see her have a mind-blowing orgasm. And I was going to try my best to give it to her.
“If you’d like me to, I will,” I answered. I smiled at her and reached across the table to hold her hand. Her skin was cool and I felt a slight tremor. I could imagine she was nervous. I was as well. After all, I hadn’t had sex in a few years.
After dinner, I took an Uber to the closest seven eleven and picked up some condoms, and got back with ten minutes to spare. I was sure she’d appreciate me being safe. If I was going, to be honest, I didn’t want to get her pregnant.
As the train pulled out of the station I sat relaxing in my room, Charlotte sitting cross-legged on the bed staring quietly at her hands. She said nothing for a long while and I was content to let her grapple with whatever was running wild in her mind.
Then, “You said that what I felt the other night was just a small taste of what I can feel?” she asked. Her voice quavering slightly. I nodded in answer.
“You know I’m a bit afraid don’t you?” I nodded again and told her that was why I haven’t pushed. That it wouldn’t be good for either of us if she didn’t want it.
Charlotte stripped off her Tee and looked me straight in the eyes. “Do I excite you?” she asked. “Am I someone that you can feel good with?”
I looked back at her and asked. “What about you?” I spread my arms. “I’m twice your age, not very attractive.” I pointed to my cane. “Not that mobile or athletic. What makes me attractive to you?”
She stared for a minute with a searching look in her eyes. So I went on. “For me, you’re a fantasy woman. You’re younger but still mature. Fit, but soft in some very attractive places. And frankly, your previous job is the stuff of some pretty dirty fantasies in itself.”
Charlotte opened her mouth, then closed it and opened it again. She finally said, “You look like a kindly Church Elder.” She quickly backpedaled and explained. “Not one specifically, but anyone. Someone who would be kind to parishioners.”
Something in what she said suddenly made her self-conscious and she folded her arms across her breasts, crushing them in and covering her nipples. I just smiled. Then asked.
“So tell me what you want.” I wanted to make it clear that she was in control. “If you allow me to do what I think you will enjoy, you won’t regret it.” I watched her closely. “But if you are unsure, don’t feel that you have to allow anything at all.
Her eyes suddenly became sharp and focused. “What do you mean by dirty fantasies about my previous job?” I smiled and motioned her over to me.
I patted my knee and had her sit facing away from me as I opened my laptop and typed in a particularly popular porn site. Then I entered the search string Naughty Nun. The first selection came back Naughty Nun surrenders to temptation and gets cream pied.
I click play and watched as Charlotte viewed the nine-minute clip with trepidation and some fascination. After a short fellatio scene, the nun in the clip was bent over and the rather large cock she’d been sucking was forced deep into her and she cried out.
Through all of it, the girl dressed in only a Wimple and black stockings with Gothic crosses on them and an iron cross hanging from a chain around her neck was yelling and crying but proclaiming how good it was and how much she loved it.
Charlotte looked back at me. “This excites you?” she asked.
“I wouldn’t say excited,” I responded. “But it is an interesting study in contradiction.” I couldn’t tell if she was disgusted or confused, but as she watched, she began to squirm.
I opened another clip titled Beautiful Nun – Bible Study. A young woman in a sheer black mini dress with leather crosses over the nipples. A crucifix on a gold chain hung between her ample tits.
She was lounging on a bed, holding what looked like a Bible, flipped a few pages then set it down beside her. Then she looked into the camera and grinned. She spread her thighs and exposed her clean-shaven pussy.
She had a shock of pubic hair above the labia shaven in the shape of a crucifix. She began running her fingers over her labia, then flexed one between them and proceeded to rub, and alternately bury one of them inside herself.
Charlotte began grinding more now. I wrapped an arm around her waist and held her in place. “Something look familiar?” I asked. She turned and looked at me sharply. “Don’t get upset. I told you this kind of thing is not uncommon.” she relaxed immediately.
“I was thrown out for getting caught doing this,” she whispered. Her voice began to crack. “The others do this as well, but I got thrown out.” She punched her thighs but went back to staring at the young woman now laying back moaning.
The Nun actress was finger fucking herself now and whispering oh God yes. Then began using more blasphemous language. Charlotte was grinding her crotch on my thigh now.
“No, that’s wrong,” a whimper in Charlotte’s voice told me she was turned on but also upset. “She shouldn’t be saying those things.” She looked back at me again searching for an answer. I smiled, then lifted my arms and began to caress her breasts.
The sudden move on my part made her gasp. “Your fingers may have felt good.” I admitted, “But I think my tongue would feel better.” Until that point her eyes had been slowly closing, she’d been letting the feeling draw her in.
She stared at me in surprise. I asked. “Shall I prove my claim?” she tilted her head to one side as if to ask a question. I continued. “I just feel that you cannot substantiate it on your own. Shall I prove my claim to you?”
All she said was, please. That was enough for me and I reached out, closed my laptop, and with some effort hefted her over onto the bed. I laid her down and unbuttoned her jeans and made to pull them off.
For a moment Charlotte stiffened. “You’ve trusted me so far.” I began.” You’ve even asked for this. I promise you will only feel pleasure from what I; mm about to do.” She relaxed and I pulled down her jeans.
Yes, folks, the carpet matched the drapes. Between a pair of beautiful creamy thighs was a well-maintained bush of chestnut-colored pubes. I leaned close and planted a kiss on each thigh before spreading them open.
Her pussy was swollen and her lips a bright pinkish red. The grinding had also gotten her juices flowing. The aroma of her sex was intoxicating. I took a deep breath and savored the thought of how she would taste.
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