Older New Friends
While recently visiting a small batch distillery in our home state of Kentucky, the owner invited my wife and I to join him and his wife to dinner. He said it was to welcome us back home, but considering how he was looking at my wife, I think he had other motives.
Mr. Roland was in his mid 60s, handsome and in good shape. We had no idea what his wife looked like but that didn’t stop my wife from accepting the invitation. She said she was simply being polite. She also said it wouldn’t hurt to make new friends.
Weeks had flown by since our friends from Georgia had visited and we toured the distillery. We were now into late fall with the holidays approaching. Amy said we needed to run to the liquor store and stock up for the holidays. I reminded her of our distillery coupons from our first trip and teased her about wearing something sexy for more. Amy surprised me when she suggested calling the owners and taking them up on their offer for dinner. After all, we were free and he seemed like a friendly guy. I said, “I’m sure he’d like to get friendly with you.” She rolled her eyes. She thinks I believe every guy is horny and out to get her, which is partly true. After all, I know how men think. I also know she’s naive about her sexiness. Maybe not every guy is out to get in her pants, but my gut tells me Mr. Roland is.
Since we were itching to get out of the house, we called the number on Mr. Roland’s business card. We explained who we were and he remembered us well, very well in fact. We said we planned to stop by and do some shopping and asked if he’d be around. He said he and his wife would gladly meet us at the distillery at 6:00. It dawned on me afterwards, that’s an hour after closing. I then realized we were about to get a different level of customer service.
The distillery isn’t large but it is impressive. The grounds surrounding it are perfectly manicured. The barns and old white oaks created a scene from a Thomas Kincaid painting. We pulled up to see our hosts on the entrance porch. They were both dressed very stylish but comfortable. He was more handsome than I recalled, which explained Amy’s willingness to meet them. He resembled Paul Newman. She was an attractive curvy brunette with extremely large breast.
We reached the porch and Mr Roland, Bill, introduced everyone. His wife Lynn wore a gorgeous sweater with a deep v- neck that showed off her ample cleavage. Not starring was a challenge. I didn’t feel too bad because Bill was checking out Amy more obviously than he did on our first visit. I believe Lynn liked the attention too. I picked up a vibe that they might be swingers.
Bill lead us inside and we chatted as we browsed the spirits and accessories. He encouraged us to pick up what we came for. Getting that business out of the way would give the staff a bit longer to prepare dinner. Amy and I weren’t sure what the dinner plans were, but now we knew we’d be eating somewhere on the premises.
The ladies were hitting it off well as Bill and I shared details about ourselves. He seemed genuinely interested in knowing what kind of profession I was in and what my hobbies are. He really like learning I am an avid outdoorsman like himself.
We made our way out to the small barn, which was beautifully lit and looked like a wedding venue. Once inside we learned that it was often used for such occasions. On this night however, it had only one round table with 4 place settings where we were waited on with 5 star service.
The dinner was perfect and the conversation good but it did feel a bit like an interview. Lynn and Bill had many questions for each of us and I still wasn’t clear where this night was going. The sexual overtones had increased. Bill kept referring to Amy as an absolute “Baby Doll”. His interest was clear. Lynn was more subtle. Her eye contact was pure seduction, but her questions were business like.
After the meal, we moved to the outdoor fireplace. The night had cooled and Lynn pulled a jacket closed over her chest. I decided to take a chance and said “nice jacket, but what a tragic loss of beautiful scenery”. She smiled and said “flattery will get you anything you want.”
Bill was helping Amy put on her jacket and looking down her top. He rubbed her arms to warm her and I knew he was eager to rub more. He was standing very close and leaned in to whisper something in her ear. I barely heard her reply but she seemed intrigued.
The older gentleman and his lovely wife had separated us for one on one conversation. We were just far enough apart to make eaves dropping difficult. My conversation with Lynn suddenly become more risqué. Perhaps I had opened the door with my compliment. Whatever the reason, the fog over their intentions was lifting. The flirting had become more open and fun. Lynn was now in total seductress mode and I wasn’t showing any signs of resistance. I think we were both getting aroused. She opened her jacket and gave her sweater a little tug to put her bountiful cleavage back on full display. I took a deep breath, smiled and stared.
Amy snapped us back to reality when we heard her heels clicking across the stone patio on her way to the ladies room. Bill walked over and jokingly asked “are you over here trying to steal my wife? “No sir, I’d never try to steal her and I’m sure I couldn’t if I tried”. Lynn winked and Bill said “I’d hope not, but I’d let you borrow her if you’re willing to reciprocate.”
There it was, The Offer. My initial instincts about Bill were correct. The Rolands were wealthy prominent people in a small town, but like many of us, they still liked a little sexual adventure. Discretion for them was obviously utmost important.
Amy returned and took my arm. It had gotten very late and we needed to talk. We thanked Lynn and Bill for a fabulous evening. I told Bill I’d like to discuss things with Amy and we’d be back in touch soon. They understood and didn’t pressure us. Bill pulled Amy in for a good bye hug. He looked down into her eyes then gave her a gentle little kiss on the lips. Lynn pressed her big breast into me hard as we hugged. She smiled and said “I hope this is the beginning of a beautiful friendship”. I replied, “me too.”
As soon as we got in the car, Amy wanted to know what just happened and what we needed to talk about. I think Bill’s kiss gave it away, but she wanted details. I asked her what she thought about them. She summarized Bill as an attractive older “horn dog” and Lynn as very warm, friendly and sexy for her age. I agreed. So I told her about the offer. She wasn’t surprised and told me she knew Lynn had the hots for me right away. She said “you were fascinated with her big tits weren’t you babe?” I didn’t deny it and noted how fascinated Bill was with her. I asked her what all the whispering was about. She said he kept complimenting her and telling her how sexy she was. He told her he had thought about her many times since he first saw her, especially when he was alone. I asked her how that made her feel and she said, “it’s nice to be desired.”
The rest of the ride home was quiet. We undressed and crawled in bed and immediately began kissing. I asked Amy if she found Bill attractive and she said yes. I kissed her neck as I massaged her breast and asked if she had felt anything interesting while standing close to him. She sighed heavily and said yes. I kept nibbling and massaging and asked if he had rubbed his cock against her. She moaned and said yes. I rubbed her pussy and I asked if she wanted me to say yes to his offer. She turned and kissed me deeply, grabbed my hard cock and said yes.
Sex that night was incredible. We both liked Bill and Lynn. Despite the age difference, we both found them sexy and knew we shared many interest. The answer was simple, just give them a call and say yes. So that’s what happened the next day.
Bill was happy that I called and very excited with our answer. He told me he’d been thinking about Amy since our first visit to his distillery. I complimented Lynn and he assured me she was equally excited and looked forward to getting better acquainted. We had to work through the logistics, which I thought might be a challenge given everyone’s busy schedules. Bill asked when we would be free? I informed him we did not have plans for the upcoming weekend. He asked if we liked horse racing and I of course said yes. Bill said, “ok, we will pick you up Saturday morning at 8:00 am. Pack for an overnight stay and dinner out.”
As soon as I hung up the phone Amy was probing for information. I couldn’t answer one question before being hit with another. I shared Bill’s instructions, which led to many other questions I couldn’t answer. I then feared she’d over pack so I told her to just call Lynn.
I got home after work on Wednesday to see Amy packing. This was uncharacteristic of her so I new she was excited and must have talked to Lynn. She began telling me they had talked for hours and she really liked her. Then she informed me we were going to Keenland for the last race of the year. We were staying the night in Lexington at the Hilton and had reservations at Jeff Ruby’s Steakhouse. Sounded like Bill had everything covered.
Saturday morning finally arrived. Bill and Lynn picked us up on time and we did a quick tour of our home, which they liked. I imagined it was nothing like theirs but they did seem genuinely impressed.
For the first half of our drive I rode in the front of Bill’s prized Land Cruiser. We shared hunting stories while the ladies talked about children and grand children. We stopped to refresh our coffee and Bill asked Amy if she minded riding up front so they could talk. He said he was certain Lynn would like to chat with me. It wasn’t long before the flirting started. Lynn and I had the advantage of no console separating us, which allowed for light friendly touching. I could hardly believe how this older woman was dripping with sexiness.
The weather was perfect for spending the day at the track. We were surrounded by fun sexy people. I learned that Lynn could hold her liquor. Bill learned that Amy had a talent for picking winners. She helped him win big and he picked up the tab for everything. He hugged her tight and kissed her for more good luck.
We left the track hungry and tingling with excitement. Since Keenland has a no denim rule, we were all dressed very nicely. I assumed we’d go straight to the restaurant but the ladies insisted on going to the hotel and changing into more comfortable clothes. Lucky for Bill and me, that meant much sexier clothes.
Bill freshened up but stayed in his slacks and pinpoint Oxford shirt. I changed into jeans and boots. The ladies, transformed from attractive to smoking hot!
Amy wore a camel colored suede mini skirt with her Frye riding boots and an off white tight ribbed sweater that had a deep V-neck lace up front. She was braless and her nipples were prominent when she got cold or excited.
Amy grabbed a cropped leather jacket and said “I can wear this if my nipples get cold.” Bill laughed and said “don’t you dare.”
Lynn finally emerged wearing a plaid pleated skirt, knee high dress boots and a silk blouse. Classy and sexy. She said “I’m sorry but I must wear a bra to hold these big girls up.” “I thought that was my job”, I replied. We all chuckled and took off.
Dinner was fantastic. I saw Bill reach under the table and rub Amy’s thigh. She briefly closed her eyes, so I’m pretty sure he rubbed her pussy too. She began running her hand up and down his leg. He never flinched, but she suddenly looked at me with her eyes bulging.
Lynn and I were subtly caressing each other as well. She opened her legs just enough to give me access to her pussy, which was getting very wet.
The restaurant kept the Roland’s signature bourbon on the self. We decided to each have a shot instead of dessert. We exited with the warm feel of the bourbon and the accumulated sexual excitement of the day.
We returned to the room and Bill broke out a special micro batch bourbon that he’d saved for the occasion. I knew one more shot would cause Amy to lose all inhibitions. We toasted to long lasting friendship. The second Lynn set her glass down she pulled me close and kissed me passionately. Bill cupped Amy’s face as if to savor the moment then kissed her slowly.
We all sat on the sectional sofa making out like teenagers.
I was kissing Lynn and rubbing her pussy under her skirt when Amy gasped and said “oh my goodness.” I looked over to see her gripping Bill’s cock through his slacks. I realized why he didn’t like jeans. I looked at Lynn who said “she’s in for a treat.”
Bill rose, dropped his pants and revealed a cock at least 10″ long and thick. I think Amy was both nervous and mesmerized. He said “you like what you see Baby Doll?” She just nodded and wrapped her tiny hand half way around it and felt its weight. It wasn’t standing at attention, so Bill encouraged her to play with it. Her hunger took over and she sucked on the head but could barely fit any of the shaft in her mouth. She wrapped both hands around it and started twisting them as she sucked. What an incredible sight.
Lynn had begun rubbing my cock through my jeans and said “it’s time to see what your working with.” I kicked off my boots and pulled off my jeans. I don’t have a monster cock like Bill, but it’s well above average size and can stay hard for hours. Lynn didn’t know she was in for a treat herself.
Amy and Lynn both stood and seductively stripped. When Amy sat down she went straight back to sucking Bill’s giant cock. He rubbed her ass and tits and moaned loudly. I pulled Lynn to me and played with her enormous tits. I didn’t forget her nicely trimmed pussy. She was very wet and stroked my cock while moaning in my ear. She told me how badly she wanted me and how ruggedly handsome she found me. I looked her in the eye and told her she was gorgeous. I slid down between her legs and began licking her pussy. I sucked her clit as I fingered her and rubbed her g-spot. Lynn began panting hard. Her legs trembled and she groaned as her first orgasm hit. It was much sooner than I expected, leaving me to wonder if Bill licked pussy.
I sat on the couch cuddling Lynn and fondling her tits while she stroked me. She leaned over and began sucking my cock. It was ok, but her skills didn’t compare to Amy’s. Speaking of whom had just laid back on the other corner of the sectional. Bill was lining up his monster as she pleaded for him to go easy. Her pussy was wet and he’d lubed his cock. He eased the head in and let her catch her breath. He went slow so she could accept his girth without pain. When he was 3/4 of the way in she begin telling him to go faster. “Oh gawd it’s so big. I’m so full. Fuck me with that big dick.”
Bill began to pump faster. Lynn was ready and climbed on my lap. She rocked slowly on my cock while smothering my face with her gorgeous tits. I sucked her large nipples and squeezed her ass cheeks. She was bouncing up and down tossing her headed from side to side. I looked over in time to see Amy’s legs thrashing as she came hard. Bill was seconds behind her. She told him to cum on her tits and he pulled out just before shooting his load all over her stomach.
At the current pace I was far from finished. Bill helped Amy up and they went to the bathroom. She returned with a bottle of water but no Bill. He’d gone to bed so Amy came to watch our show. She sat quietly watching, but it wasn’t long before she was rubbing her pussy. Lynn had tired so I laid her on the sofa and started pounding her. She screamed “Oh damn” as another orgasm hit. I never let up. Amy patted her own pussy and said she needed a toy. Since we didn’t have one handy, I had her scoot closer to finger her pussy. I could tell she’d been stretched and she was incredibly wet. She laid against Lynn with her face on Lynn’s breast. Damn this was so hot.
Amy started talking dirty and Lynn began to get into it. Amy said “he’d love to fuck your ass.” “Would you like his cock in your ass Lynn?” Lynn panted and said “oooh yes please, Bill’s too big.” I pulled out my well lubed dick, pushed Lynn’s legs back and rubbed the head of my cock on her tight brown hole. I pushed slow and easy until my head broke past her tight ring. Her gasp trailed into a moan. I went deeper and started a slow rhythm. Amy cooed and rubbed Lynn’s nipples. I told Amy to rub her clit and that sent Lynn over the edge. Her ass gripped my cock like a vice. I felt my orgasm welling and pumped faster. Lynn’s legs began to shudder as I exploded into her ass. We laid in a pile for a few moments catching our breath. The whole experience was amazing.
Lynn went off to bed with Bill. Amy and I cleaned up and snuggled naked together. I asked her to honestly tell me about her monster cock experience. She said it was fun and explained that being so stuffed felt good. However, she complained that it just didn’t last long enough. I told her next time I wanted to watch more. “Next time,” she asked? “Sure, now how about a normal cock” I asked? “The fact that your hard again means there’s nothing normal about your cock.” I rubbed it against her wet pussy and she told me she needed more. I entered her and started pumping slowly. She ordered me to get on top and fuck her. “Fuck this pussy,” she ordered. We fucked hard and fast until we both came.
We left early the next morning and grabbed breakfast on the way home. The conversation was warm and friendly. Bill and Lynn both said it was the most fun they’d had in quite some time. Bill then apologized for his lack of stamina. Amy quickly assured him she had an incredible time and could only take one round with his monster cock. He blamed her oral skills for getting him worked up so fast. I was shocked when she said, “let someone else drive and you can have more of that on the ride home.” Bill tossed me the keys.