This starts with a random encounter but turns into much, much more.
Its Saturday morning and I have several errands to run. Another football season is upon us so that means college ball all day Saturday and NFL on Sunday. The wife and I are expecting company so we’ll need groceries, beer and booze for the weekend. One of the reasons I like doing the shopping is I get some alone time to jack off in my car on the way home. It’s something I’ve done for years and I’ve had some really good orgasms.
My excitement is building as I head out in my SUV and the grocery store is my first stop.
I walk through the grocery store and admire all the women as they go about their business. As they pass me in the isle I like to stare obviously at their tits if they are alone. They never say anything but I like how uncomfortable it makes them and causes them to pull a sweater closed to cover their tits. This always makes my cock start to get hard and I hurry through the rest of my shopping and other errands.
It’s a warm September day so I’m only wearing shorts and a t-shirt as I get back in my SUV. Today was a great day at the store as there were many women for me to stare at but it made me horny as hell. I really need to jack off so I push my shorts down around my ankles as I head out of the parking lot. My cock is immediately hard and I start to stroke it as I head up Route 91 toward my house. I’m not too far away but know I can take a few detours through back roads if I need additional time to get off.
I pass through the traffic light at State Road and prepare to take my first detour down Farm Road when I notice a girl hitchhiking on the side of the road. She’s very hot and looks to be in her early 20’s and I start thinking about what could happen if I give her a ride.
I pull my shorts up, put my signal on and pull over. She runs over to the car and jumps in. “Thank you so much for stopping. My car broke down at the mall and I really need to get back to Wallboro because I have labs this afternoon and I’ll be in deep shit if I miss that.”
“No problem, I remember what college is like. I’m Tony by the way.”
“Hi my name is Mary Ann. It’s nice to meet you and thanks again.”
Although I had pulled my shorts up my cock was still fully hard and all eight inches were pushing against my terry cloth shorts. Mary Ann’s eyes widened as she noticed but she didn’t say anything right away. I said, “The thing is Mary Ann, I have a pretty tight schedule today and I need to get home before football starts so this is going to set me back a bit.”
“I’m sorry to inconvenience you like this but I am really grateful that you picked me up,” she said.
Feeling a little bolder I started feeling my dick through my shorts and said, “It shouldn’t be a problem. It’s a nice day for a drive and it’s nice having a gorgeous girl like you to keep me company.”
She said, “Can I ask you something Tony?”
“Sure Mary Ann,” I replied.
“Do you always drive around with a huge hard on like that?”
I laughed and said, “I wouldn’t say always but I have a house full of people and I didn’t get a chance to cum this morning so I was just starting to take matters into my own hands when I saw you.”
“Wait, you were masturbating in your car when you picked me up? Isn’t that dangerous?”
I glanced over at her and said, “Why yes I was Mary Ann, I’ve done it for years and never had a problem. I have a really strong sex drive and if I don’t get off every day I’m totally out of sorts.”
She said, “So you’re telling me you cum every day?”
“That’s right, Mary Ann and usually more than once if I can.”
“Wow, that’s amazing,” she said. “So what was the most times you got off in one day?”
“A couple months ago I was home alone all day and came six times but I think my record is 10.”
“So you sit around all day naked and alone and play with yourself. How do you stay excited? Do you watch porn or something?”
“Of course I do Mary Ann. I have multiple devices so I really like to connect with people online so they can watch me and see the porn I’m watching and I can see them too. It’s mostly men who do that but I have a few women who really like watching me jack off while they play with their pussies.”
She thought for a while then said, “I assume you want to have me watch you jack off then. I won’t mind if you take your cock out and I kinda want to see it.”
“I thought you’d never ask,” I said and pulled my shorts down around my ankles to free my raging cock and started to stroke it.
“Jesus Tony your cock is huge. Most of the guys at school have little pencil dicks and they cum as soon as I put a hand on them so I usually have to finish myself off when I get back to my room. I’d be happy to jerk you off in return for the ride home.”
“I would absolutely love that,” I said. “You know it can be tough for younger guys especially when the feeling of putting their cock in a hot pussy like yours is new to them. My suggestion is to be patient and wait for them to get hard again then fuck them all night long.”
She grabbed my cock and started to stroke up and down my shaft slowly. “I’ve heard that as men get older it takes them longer to cum. Is that true?”
“I can’t speak for all men but in my case it is. Even when I jack off it usually takes me at least an hour to cum.”
She said, “I don’t think I’ve ever fucked anyone for an hour before,” then she turned her attention to my dick. “You have a beautiful cock Tony. It’s so hard but the skin feels so soft at the same time and it’s the biggest one I’ve ever seen in my life. It’s not only long but fat as well.”
“I’m glad you like it Mary Ann, this feels really good,” I said.
“I have to admit that this is making me pretty horny right now. I can’t imagine what a dick like yours would feel like in my little pussy. Would you mind if I put it in my mouth? I’ve never sucked a dick like yours before and I need to see what its like.”
“Be my guest babe,” I said and she leaned over and took my cock into her sweet mouth. She started sucking the head but wasn’t able to take my length all the way into her mouth so she continued to stroke my cock at the same time. The feeling was amazing and I enjoyed glancing down at her as she sucked my dick.
“Oh it tastes so good but it’s so big I can’t fit the whole thing in my mouth. Does this feel good?”
“It feels amazing and I was not expecting this when I picked you up. I figured I’d be lucky if you agreed to watch me jack off. Oh yes keep sucking that cock for me Mary Ann.”
She continued sucking my cock as I drove then she said, “This is making me really fucking horny and I can’t imagine what your big dick would feel like in my pussy. Like I said, the guys at school are not very good at fucking so I think I want you to fuck me.”
I said, “Are you sure Mary Ann? Fucking you is the only thing I’ve thought of since you got in the car but I don’t want you to do anything if you’re not sure. If you really want me to fuck you I know just where to go where we can have some privacy.”
She took off her pants and started playing with her pussy as she continued to jack me off.
“There are plenty of things in my life that are confusing but needing your cock in my little pussy is not one of them so take me wherever you want. I hope its close because I need your cock right now. This is so sexy I feel like I could cum.”
I looked at her perfect pussy and said, “Don’t do that Mary Ann. You’ll enjoy it more if you let me work my magic on your body.”
She slowed down and pulled her legs up on the seat giving me a perfect view of her hot young pussy. I reached over and stuck a finger in her then brought it to my mouth so I could taste her young sweetness.
“Oh my Mary Ann, your pussy tastes wonderful. It’s been a long time since I’ve had a hot young pussy like yours and I cannot wait to stick my tongue in you. I know a place where we can go and it’s just up the road.”
I headed toward the small cemetery that was located just off Route 91. It was one of my jack off detours and it had a small dirt road in the back that led back into the woods. I think the caretakers use it to dump grass clippings and so on but they never worked on the weekend and I always had the spot to myself.
I pulled in and there were no cars in the cemetery yet which was good so I made my way back to the utility road, eased my SUV to the end and killed the engine. Mary Ann got up and kissed me as she continued to stroke my cock. “I need your cock in me now Tony. How do you want to do this?”
“Just one minute babe” I said. I got out and dropped the middle seats down so we had the entire back of the SUV. Mary Ann quickly jumped in the back and took the rest of her clothes off. She was around 5’4” and was fit and thin with perky little tits and a nice round ass. She had shoulder length brown hair and bright blue eyes that were stunning. “God you are beautiful.” She actually blushed at my compliment and I leaned her back and started to run my hands up and down her lithe body as she stroked my cock.
“Oh that feels so good” she whimpered. I made my way down to her pussy which had a small patch of pubic hair and started to feel her clit.
I took a minute to admire her hot little pussy and said, “Wow, your pussy is perfect, I can’t wait to fuck you.”
She moaned with pleasure as I took one of her nipples in my mouth and lightly sucked and bit it. “Oh fuck yes” she cried. I started to kiss her from her tits down her belly until I made my way to her pussy. I first plunged my tongue into her so I could taste her young sweetness and it was pure heaven. She cried out again as I started to lick her clit. “Oh God you’re going to make me cum already!” I stuck a finger in her and she started to buck against my face as her little pussy tightened around my finger as she came. “Oh fuck I’m cumming right now. Oh God it feels so fucking good! MMMMMMMM.”
Her juices flowed freely from her pussy and I couldn’t wait any longer to stick my cock in her. Her eyes were closed and she was breathing heavily as I got on top of her and positioned the head of my cock outside her pussy. “I wish I wouldn’t have cum so soon. I would have liked to cum with your cock in me,” she said.
“Don’t you worry about that Mary Ann. I’m just getting started with you.” I slowly started to slide my cock into her but she was so tight I could only go in a bit at a time even though she was soaking wet. “I need to take my time because I don’t want to hurt you with my big cock.”
“OK Tony, do what you think is best but hurry up and stretch my little pussy because I want that massive cock all the way in me.” I slowly pushed in a little more and pulled out, getting a little deeper each time until all eight inches were buried in the tightest pussy I’d ever felt in my entire life. At this point in my life it usually takes me a while to get off but her pussy felt so soft I wasn’t sure how long I could hold off.
“My God Mary Ann your pussy feels so good on my cock. It’s been a long time since I had a tight little pussy like yours.” I started to fuck her harder with long slow strokes. Her breathing picked up as I fucked her faster but always paused when my cock was all the way in so I could grind her clit.
“Fuck this is so fucking amazing, I never had anything in my pussy like your cock. It feels so full in my tiny pussy and I love the way you grind on my little clit like that. Push all the way in Tony I really want to cum on your cock.” I did as she asked because I was really getting close to cumming and grinding on her like that helped me hold off. She grabbed my ass and started grinding her clit harder until she came again. “Oh God I’m cumming again Tony. Please pound me hard with your cock while I cum!” I didn’t need to be told twice and I started pounding her sweet pussy with everything I had. “Oh fuck yes! Just like that. I’m cumming again! MMMMMMMM!”
Her body shuddered with her orgasm and she grabbed my face, started kissing me and stuck her tongue in my mouth. That did it for me and my orgasm started to build. “Fuck Mary Ann you’re going to make me cum!”
“Don’t cum in my pussy Tony. I want to taste your cock and sperm OK?”
I didn’t reply but continued to pound her sweet pussy as my orgasm continued to build. At the last second I pulled out and positioned my cock outside of her mouth. She grabbed my cock and stroked it hard and fast with her mouth open. I was still working up to an orgasm and she sucked my cock into her mouth and continued to jack me off. “Oh Mary Ann here it comes. Get ready.”
She pulled my cock out, continuing to jack me off and said, “I have to see the cum shoot from your big cock. Oh cum all over my face Tony.”
That did it and I started to cum on her. “Fuck Mary Ann I’m cumming. Oh yes jack me off baby. MMMMMMMMM!” I started to shoot stream after stream of cum on her face and into her open mouth. I came so hard I shot cum into her hair and over the back of her head onto the front seat. Before I was finished she stuffed my hard cock in her mouth and swallowed the final drops of cum.
We both collapsed into each others arms and she said, “Jesus Tony that was fucking incredible. I’ve never been fucked like that before and my little pussy feels like it’s still quivering. I can’t believe how much you came and I love how you taste. I’m not sure how I’m going to go back to those immature college boys after this.”
I replied, “You are an amazing woman Mary Ann and I absolutely loved fucking you. How old are you by the way?”
“I’m 21 Tony and you?”
“I’m 58 years old Mary Ann.”
“No fucking way” she replied. “I would have guessed 40 max.”
I said, “Why thanks for the compliment Mary Ann. That’s the nicest thing anyone has said to me in a long time.”
“You are incredible Tony. Do you think you would be able to come and fuck me again sometime? I have an off campus apartment that I have to myself every Tuesday. I don’t have classes that day and my room mates all have full schedules so we could have my room all to ourselves. I can’t imagine how many times you could make me cum if we spent the day together.”
I said, “That sounds wonderful. The thing is I’m married but my wife is planning a trip to Florida next month so I think I could come for a visit then if you don’t mind that I’m married.”
“I wouldn’t care if you had two wives as long as you save some cock for me. Your wife is a lucky woman and I hope she takes good care of you. I’ll give you my number and you can let me know when you’re free OK?”
“Sounds like a plan” I said. “I have a trick that I haven’t shown you yet and I can make you cum a bunch of times in a row.”
“Really Tony, wow. I’m not sure how you could do that but I can’t wait to try,” she replied.
“It’s a date but I better get you back before people at home start wondering what happened to me.”
We got dressed, put the seats up and headed to her apartment. On the way I started thinking of fucking her all day and my cock started to get hard again. She noticed and slid it out of my shorts and started to jack me off. “This is what you wanted me to do when you first picked me up isn’t it?”
“Sure, I figured if I could persuade you to jack me off it would be amazing. I never thought I’d end up fucking you.”
She said, “Well you’re going to fuck me a lot, now let me jack you off daddy.”
She continued to stroke my massive cock and as we pulled into the parking lot of her apartment complex I shot another huge load all over her shirt and pants. “Fuck Mary Ann that was amazing but I sure made a mess on your clothes.”
“Don’t worry about that Tony” she said. “Maybe my room mates will notice and I can tell them what happened. I think those bitches are all horny as hell so you might end up fucking a couple of us at some point if I feel like sharing you.”
All I could say is, “Oh my.” She gave me her number and a long passionate kiss.
“I’m so glad I met you Tony and I’m looking forward to seeing you again. I hope you don’t forget about me.”
“Not a chance babe” I said. “I’ll be in touch soon.”
With that she got out of the car and made her way to her apartment. A couple girls met her outside and looked like they were asking questions. She just pointed back to me, waved and went into her apartment.