I have been a part time limo driver for twenty years. I have seen it all in this line of work, but not until recently, did I ever participate in any of the afterhours activities.
After my wife passed away, which was over five years ago, it was a hard transition at fifty-two to be single. As soon as the word got out that Jimmy Fitzgerald was a free agent, I was inundated with food, phone calls and offers of sex. I was pretty taken back when one of my wife’s good friends seduced me and offered me a regular day every week for her to come over and screw me. I refused her; I knew her husband, and one slip up was enough for me.
Now two very attractive women, I say women because these chicks were not young, but both of them were attractive and in great shape. They were on their way to see a play in the city when one of them knocked on the inside window. I hit the button to open it, and she spoke to me.
“I’m curious, are you married?” her soft sexy voice said. I tried to imagine if it was the red head or the brunette that was asking the question. Both women were well preserved and lovely.
“I’m a widower; my wife died a few years ago,” I answered her.
“Oh, I‘m sorry," the same voice answered.
“Yeah, she was a great gal. We had a pretty good marriage,” I said meaning every word. I still missed her.
“Mr. Fitzgerald, that is your name correct?” she asked.
“Yes it is,” I answered her.
“Look, it’s my friend’s birthday. She has a bucket list, and Mr. Fitzgerald, would you like to help us with one of her listed items?”
“That all depends,” I added.
“Oh, it’s not kinky or anything. It’s actually something we probably all think about but never do," she said.
“Okay ladies, you need help? Now, what on that bucket list can I assist you with?” I told them, confident that the two women in the limo were no threat to my life.
”Oh, Mr. Fitzgerald, thanks, because I think all three of us are on the same page.
Have you ever had a threesome?” she asked.
I almost stepped on the brake but kept my composure. I was wondering if I heard her right. A threesome? Shit, my cock rose a little in my boxers. Just the thought got my juices going; I guess because it has been a hidden desire I have had since college. It also could be because I had not been with a woman in a while and I jacked off on quite a regular basis.
“Uh, Ladies, did I hear right?” I asked them.
I heard a sigh, then one of them spoke again, “Yes, but if you would rather pass, we understand. Look, we are not into each other. We just saw you; and I don’t know, you are a nice looking guy. It seemed as though we could maybe trust you. Oh, God, this is embarrassing. Would it make it any easier if you knew that neither one of us ever did anything like this before? Jane is a widow, and my asshole husband divorced me last year. We have been friends forever and have no problem getting it on with one guy. My name is Trudy. Jane and I talked this over, and well, you seemed safe, attractive, and God you are available,” she said. “But it’s okay if this is not your cup of tea, just forget we mentioned it.”
“Maybe we can talk.” I surprised myself. I know the two women in the back seat were both attractive and well preserved. What the hell, it was worth discussing.
“Really!” one said loudly.
“Jane, did you hear he wants to talk?” the other said.
“How about we get to know each other? Maybe a nice small inn along the way here, we can stop and have a drink and talk,” I suggested.
“Sounds great. Hey, what the hell, right? None of us is getting any younger. Damn, the younger ones do this all the time. Just last week my oldest son was with two girls. I heard him on his phone. Now, I was appalled at first, but when I told Jane, she shocked me and told me it was something she also fantasized about doing. Then, she produces this list: a bucket list. And well, here we are.” now I knew it was Trudy speaking.
“Okay Ladies, there is very quaint little pub called Orlando’s a few blocks down. We can get a booth and relax, have a drink, and get to know each other. I’m fifty-seven, and having two lovely women in my bed will require some ground rules,” I said.
“Oh, this is exciting!” Now I knew that had to be the redhead, Jane.
“Here we go, Ladies,” I said as I pulled the limo into the parking lot of Orlando’s.
I got out of the car, went around to their door, and opened it. I saw one very nice calf come out onto the gravel of the parking lot, then the other; and with that, the very attractive brunette called Trudy emerged. She stood before me; and I got a very good look at her, and my damn cock pumped up a bit more. She was lovely, and the dress she wore was low cut, showing off a real nice set of tits.
She held out her hand, “Hello, Mr. Fitzgerald, I’m Trudy, the divorced one. Got a first name?” she asked her voice low and sexy.
“Jimmy and how do you do, Trudy?” I said smiling like a Cheshire cat.
"Trudy?” the voice from the car echoed.
Another well-formed calf hit the gravel as Jane, the stunning redhead, alit from the limo. She was a little taller than Trudy and Irish looking, as opposed to Trudy's darker, obvious Italian, heritage; but both of the women standing before me were very attractive.
I had all my life tried to keep my weight under control, but damn, I like the sweets and unfortunately the beer. So, keeping my love handles and stomach down to a minimum was a chore. Since my wife was gone, it was easier to keep my weight down; I just never shopped for food. The tuxedo I had to wear driving also helped, and the full head of white hair I still had always helped. My clear blue eyes needed contacts to see distances. Being my one vice, I was a bit vain about my sight and eyes.
I bowed to the two of them causing them to giggle like two seventeen year olds, and I had to smile. I was really getting into the whole idea.
I held out both of my arms, and they hooked theirs into mine. It felt good to have two very pretty women holding on to me. We were seated at a table in the back of Orlando’s. It was nice and private. I was glad; the subject we were going to discuss would certainly raise a few eyebrows.
The waitress came to our table, and I looked to the two pretty Ladies.
“What would you like to drink?” the waitress asked.
“Mmm, let me see”, Jane said. “A rum and coke, please.”
“White wine, please,” Trudy said.
“Cold beer, please,” I added
“Okay, who’s going first,” said Trudy.
“I think it should be me,” said Jane. “It is, after all, my bucket list.”
Trudy and I both sat back in our seats and let Jane talk.
“I am fifty-seven and have never been hornier. You, Jimmy, are quite attractive. Do you find me, well, attractive too?” Jane asked.
I wasn’t lying when I answered her, “Very.”
“God, thanks. Now, I know Trudy hates when I do this, but she is fifty-six. There it’s said,” Jane said.
“Okay, Jane, so I’m fifty-six. Fuck it. It is what it is,” Trudy added.
“Now, both of us are done with menopause and free to have sex whenever. We both masturbate a lot, more now than ever. I have always wanted to share a guy. I love to watch, and Trudy loves to show off. We talked about what we will do sexually and really are not into each other, but if that turns you on, we’ll experiment. We both have no problem with oral sex, giving it and getting it. How about you?” she asked
Damn, I was getting hard again just listening to this very pretty woman talk. I watched her mouth, her shiny lips, and I imagined them sucking my very eager cock.
“Ladies, I love pussy and have no problem eating both of yours. Actually, there isn’t much about a woman’s body that I don’t like,” I said to them
“Jimmy, where do you think we should stay for the night? You know this is on us: all of it. It’s something we started, and it’s Jane’s bucket list,” Trudy said, rubbing her leg next to mine. I then I felt Jane’s hand on my knee, and again, my cock began to harden. These two weren’t kidding. It was time to tell them about Friar’s Inn: small cottages and perfect for our little tryst.
“Friar’s Inn is perfect, Ladies: clean, well decorated, and great food. Their cottages are lovely, and they all have King size beds. Affordable too,” I added.
Trudy’s hand replaced her soft knee, went right to my crotch, and met Jane’s questing hand. They both grabbed my cock, which was hard and still growing. One cupped my balls, the other my cock, and I knew it was time to leave.To be continued:
We barely made it to the limo. I never wanted to fuck so bad in all my life. Now the thought of two women to play with was making it hard for me to keep from blasting off inside my damn trousers. I had to pull back my thoughts; I still had to drive the few miles to Friar’s Inn.
“Ladies could you do me a big favor?” I asked as they got in the limo.
“Anything Jimmy,” they said in unison.
“Could you look up the number to Friar’s Inn and make that reservation? This way I can pull up to the office, get the keys, then all we have to do is pull up, get out, and run into the room.” I sat in the front seat and started the car.
Jane giggled. “I like the sound of that.”
I was grinning in the front seat. I placed my free hand down to my crotch. Shit, my cock was hard. I’m not gonna lie, it felt fucking great. As did my thoughts of what the evening might bring. My damn mind was in the gutter.
My wife never complained. We had a good and active sex life and were still very much in love. There were mornings before work when all I wanted was to burry my face between her legs so she could scream with need. Then I’d get her on all fours, and she’d be so slick from her orgasm that I could ride her hard. Those mornings stuck in my mind. I missed them. I missed her. But life went on. And tonight I was going to enjoy myself.
Tonight was the beginning of Jimmy’s new leaf. Especially if this was any indication of what life could be like single. There were plenty of attractive mature women out there looking for a man. My hand again rubbed my cock, oh yeah, and this was just the beginning.
I saw the sign for the Friar’s Inn, a quaint and well-maintained place. My excitement grew along with my damn cock. “Ladies, we’re there.” I turned and looked through the small limo window. “I need to tell you that if you have changed your minds, I’m okay with that. I don’t want you to think…”
A sexy voice floated through the small window. “Jimmy, we’re raring to go, but if you’ve changed your mind, we will understand.”
“Ladies, then it’s a go. Houston we have lift off.”
I heard giggles from the back seat. Now that really turned me on, because not only was this going to be sexy, it was going to be fun.
I got out of the limo and opened the door. “Ladies, we’re here,” I said as I helped them out. Now I could see the two of them were feeling no pain after the gin and tonics they had. I, on the other hand, had to drive so I was fine. I also kept in mind that I needed to please two women, so my cock needed all the attention they could give it. I had to grin, I’m sure they would be giving it plenty of attention once we got into the room. I did have one fear and I didn’t want to go off half-cocked before we had a chance to have some fun.
I took a few deep breaths and let each one of the women take an arm. The night air was pleasant, and I wondered what the clerk would think when we entered the office and asked for a room. I wasn’t sure what to say or do, so figured I’d play it by ear, but that again wasn’t necessary, my two lovely friends took care of that for me
Trudy took control. "Young man, we just called about a reservation. We would like a king size bed please," she said as she passed him her credit card.”
The kid never blinked an eye as he checked the computer. “I have a real nice room, facing the water, here’s the keycard, room eleven thirty-three. It’s a bottom floor.” When the kid raised his head, I winked, and he just gave me a small wry smile.
It was now pitch black outside, and the sky looked like a velvet sheet hovering above us. You could see the moon in the distance, but the stars seemed to be further away, more so than usual. I was excited, and yet I had mixed feelings. I’d never done anything like this before; I was praying it was all it was hyped up to be.
The three of us stood outside of room eleven thirty-three. The girls gripped my arms. I had to tell them one more time. “If you are having second thoughts, please say so. I don’t want to do this if you are ladies are having second thoughts.”
They held onto my arms tighter. Jane opened the conversation, “I wouldn’t miss this for the world and you, Trudy?”
“It’s a go, and you, Jimmy,” she said holding onto me as she looked up at me.
I slipped the keycard in the slot, and the little green light came on. I could only grin.
“Oh, yes,” Trudy squealed.
I had to laugh; this was going to be a very interesting evening.
The room was big, clean, and beautifully decorated in mid revolutionary war motif. Rich blues and warm beiges brought to life the dark furniture and huge four-poster bed. The girls and I shed our coats then sat on the bed. Jane got the ball rolling.
“Well, we’re here. Who wants to go first?” she asked, before letting a small giggle escape.
I must say I surprised myself when I stood and turned around to face them. “How about I go first? Usually it’s ladies first, but in this case…” I unzipped my trousers. The girls moved together on the bed. Jane rubbed her hands together and Trudy licked her lips. They looked like two schoolgirls waiting for the quarterback at a party. That turned me on. My cock had softened some, but now it had begun to come to life. “Should I show you more?” I asked and grinned, with what I hoped looked sexy.
Jane moved closer to my abdomen and rubbed her hands down the length of my zipper. My blood began to flow. Her hands slipped between my legs and she cupped my balls smiling up at me. Trudy now bit her bottom lip. Trudy’s hands undid the button to the top of my trousers.
“Step out of your shoes, Jimmy,” Jane commanded and I obeyed.
Two sets of hands slid my trousers to the floor leaving me in my boxers. Those came next, allowing my hard-on to stand freely in their faces.
“Oh, fuck,” Trudy said.
“Yes,” Jane added, “Let's fuck him with our mouths.”
Warms hands cupped my exposed balls, and a mouth sucked me in. I closed my eyes. It had been ages since anyone sucked my cock, and it felt amazing. I loved my balls fondled, and the hands on me now where driving me crazy. The blood rushed to them and they began to tighten. Instinctively, I grabbed a hand full of hair from the mouth sucking me. When I gazed down it was Jane. I closed my eyes and concentrated; the goal was not to cum. The hands on my testicles massaged me; the dual attention was bringing me around fast. As much as I hated to stop them, I had to. It was my turn to arouse them
“Ladies,” I said quietly as I pulled my cock from them. “I don’t want to cum, not just yet. What I would like is to have you two naked and spread out on this bed.”
“Well then, Jimmy, we need your help,” said Jane.
“Gladly.” I had them both stand before me. “Kick off those heels. You can put them back on later. I have always wanted to fuck a woman in heels.”
“Ooh, you are a bad boy at heart,” said Trudy.
They turned and I unzipped both their dresses, letting them fall to the ground. Next, they stepped out of them beforethey turned to face me. I was surprised; they both had gorgeous skin and great bodies. Like I said, we were all three in our fifties, but I now realized my tastes ran toward my own age bracket and that excited me. I had loved my wife and enjoyed that we were still excited sexually by each other after our many years together. I wanted that again…someday.
Before me stood two very attractive women, who by the way wore some very sexy lingerie. My eyes were treated to black lace and satin, which did little to cover ample breasts and hips. My cock kicked and jerked, causing a few giggles. “Ladies to the bed. Let’s test my stamina.”
“And that tongue,” said Trudy in one hell of a sexy voice.
“Yes, my tongue.” My cock jerked again. Shit, I was hot, hotter than I’d been in a long time.
They both went to the bed and made themselves comfortable. Jane raised her hips and slid off her panties. “Come here Jimmy, come to momma.”
Ah fuck was all I could think of when I saw her close cropped pussy. Trudy just smiled. I figured it would take a little time for her to warm up, so I came to the bed and spread Jane’s legs. Trudy got up on one elbow to watch. I smiled at her and let my tongue run along my bottom lip. I parted Jane’s lips and stuck a finger inside her and she moaned.
‘Oh, Jimmy, oh yes,” Jane said.
I took it out, licked it, and saw Trudy’s eyes widen. “Oh my,” she whispered.
She leaned back and took off her panties, now exposing her bare pussy. She spread her legs wide, and I bent my head down to lick her smooth lips. I continued to fuck Jane’s pussy with my fingers and now delved into Trudy’s cunt with my tongue. My thumb found Jane’s clit and my tongue found Trudy’s. I began to work on both of their knobs of pleasure. A lick, a rub, I was sinking and getting deeper into their whole scene, and my hard aching cock could attest to that.
Trudy came first with her fingers entwined in my hair. Her gush of juices gave me all I needed to know. I left her pussy and buried my face in Jane’s determined to feel her pleasure. I found her little swollen pear, sucked it into my mouth gently, and used my tongue to arouse her even further. Her hips rose from the bed as her fingers held my head fast by my hair. But she still needed more stimulation. I lifted my head and let one hand move up to Jane’s breast.
“No,” Trudy interrupted. “Let me, you continue eating her; I’ll play with her breasts.” Then Jane opened her eyes and nodded.
“Oh, god yes, Trudy, yes,” Jane said breathlessly.
Trudy moved close and used her fingers to tweak Jane’s breast. Then said,” Oh what the fuck,” and lowered her head and began sucking her tits.
Fuck, this was hot. This was the hottest scenario I’d ever been involved in. I went back to the pussy before me and got right to Jane’s clit determined to make her cum. It didn’t take long for her to arch her back and scream.
“Oh my fucking God!”
They both fell back on the bed, a little winded and now my cock was more than ready. My hands went to my dick, and both yelled.
“No!” and got to their knees and on all fours. Both pussies were offered and I was taking them. I entered Trudy first, thrusting hard into her.
“Smack my ass, Jimmy,” she pleaded, her voice low and sexy. As I came out, I slapped her cheeks and did this several times. I knew it was time to change and then next rammed into Jane. She was more than ready as I fucked her hard, and she came again as her pussy clenched my cock. I was seeping, aching, almost wild with need when I heard Trudy.
“Please, now, oh please,” she pleaded.
It took every thread of will power I had to pull out of Jane and push back into Trudy. But I did and rammed hard. My abdomen and balls were so tight I wanted to scream, but I needed a fucking condom. Jane’s hand came up and she’d already opened one.
“Let me,” she said, as I pulled out and she slipped it on me. “I want to watch this,” she added.
Can I say that was the hair that broke the Camel’s back? It took two more strokes and I came, gushing hard. I was able to push a few times more into Trudy before her pussy contracted only adding to my own orgasm. The three of us collapsed on the bed, both women wrapping themselves around me. I held them both, thinking, I could get used to this, but also realizing this was probably going to be a one-time affair. We fell asleep, waking up at about three a.m.
“Jimmy,” Jane said. “I hate to break this up, but we need to get home.”
I understood her meaning and smiled. Trudy then sat up and smiled, but said nothing. We dressed without saying a word and it was Trudy who broke the ice.
“Thank you, Jimmy. This has got to be the wildest thing we’ve ever done.”
Jane added, “But real life and reality comes around to bite you in the ass.” She sighed. “To me, for us to get home. Maybe we’ll call your services again in the future,” she said. However, I knew that was probably never going to happen.
I returned them home safely, kissed them both, and went on my way. I had to shake my head. Had that all really transpired? It did, such is the experiences of a limo driver.
Stay connected….for more free short stories…Ethan Radcliff copyright 2015 as The adventures of Jimmy