Author: winksandwhispers

48[F] Milf Bait in the Big Easy

I made sure I got there a bit later in the evening. New Orleans was hot, and this piano place could make you a sweaty mess if you were there too long.

That night I was wearing a wide strapped black cotton dress that crossed over in the front. It hung beautifully and looked super-hot with my black patent strappy heels. (Note to self: No more heels in New Orleans).

I was out with a longtime friend and just about to take a sip of my second Hurricane when he approached me and asked me to dance. “People dance here?” I thought.

I obliged him and we danced very closely as the first hurricane kicked in. His friend asked my friend to dance and then within 30 minutes there were 7 guys from a steamship conference at our table. Drinks flowed almost as fast as the laughs. I was lost in his eyes. He never stopped touching me. The rings on my left hand did not bother him and the ring on his left did not bother me. Read more »

47[F] Naples Pier

So after a late afternoon of drinking, I left my sunbathing and sat at a bar a little farther down the beach. There was a fishing pier nearby and I noticed a few guys fishing. The bartender was a pretty handsome guy originally from Brooklyn and despite my somewhat inebriated condition, he kept me drinking and laughing with his stories about NY.

His shift ended at 7 pm. He asked me if I wanted him to walk me back to my hotel. I was thinking my friends might getting worried so I thanked him and we proceeded out the door. He grabbed my hand after we exited and asked me if I had ever seen the pier. I had not.

We walked past the spot where I had seen the fisherman earlier and he kissed me full on the lips. I was caught off guard but he was hot and fun. Why not?!!

So he takes me to the other side of the dock. We sat for awhile on this picnic bench and he starts to kiss me again. It did not take long before, he slipped his hands inside my cross-over top baring both of my full, round breasts. As expected – my nipples were fully erect. Read more »

46[F] What Happened Last Night in SF

Having never been to San Francisco, I made plans for a few extra nights before my conference so I could experience the town and get some much needed rest in the hotel. Conference rates on high end hotels are always a good thing.

With all of the excitement of the trip, I did not take a moment to consider that I really do not like traveling around on my own. Not to mention, I heard several scary stories by women traveling alone there. I thought “Whatever, I will survive”.

After a harrowing ride from the airport, I got into my room and thought about where to head. There was a hotel bar on the rooftop and there were at least 3 people in the elevator that were headed up there. I get dressed to go up and figure I can have a drink and then settle in early before hitting the town the next day. Read more »

46[F] Professional in DC – Hotel Meet Up

I admit that I was nervous. This meeting had been set up online for over a week. We were both married and I had never hooked up with someone I met online. I

So there I sat at 430 pm at the bar of my boutique hotel. Busy enough that we would not look out of place and quaint enough that we could get to know each other in a more intimate setting.

He was a bit thinner and shorter than the guys I had hooked up with in the past. When we messaged online, he confessed his fantasy of being with a woman who had nice big tits and a round ass. He had married early in his life to a girl he met at their Jewish summer camp so his sexual experiences were so somewhat limited. While he didn’t have a “type”, it turned out that all of his trysts were soccer Moms who could easily be confused with his wife. None were able to fulfill his fantasy. Read more »

47[F] Yes, I Do Lunch.

One of the guys who worked for a vendor of my employer was flirting with me hardcore. It was so over the top, it was hard to ignore.

When he asked me to lunch, I knew he had plans. BIG PLANS.

He was a few years older than me with a decent physique and this awesome smile. No wonder he was in sales. I was really attracted to his longer lean physique with great muscle tone. Meanwhile, I was informed multiple times that he loves big tits and a round ass. I delivered.

Parking was tight at this lunch place and he was running late so he parked down around the corner. After lunch with drinks and some heavy flirting, I drove him to his car in my SUV. As he exited, he put his right hand on the door handle and then grabs my chin with his left. He pulls right into me and starts kissing me. Very passionately. I was in. Definitely in. Read more »

46[F] Girls Trip to Fort Lauderdale

Picture this! Trying to survive a very long cold winter, you take a trip with your five best girlfriends to a beach house in Fort Lauderdale. Most are married, including yours truly. We hit the town with a vengeance and end up at a beachside bar. I am wearing a cotton crochet dress with heels…. hair down and just so happy to be away from all of my obligations.

He approaches me. “Do you want to dance?”

I oblige.

The night is a whirlwind.

I am trying to hide from my friends so we can make out like two teenagers.

He is a great dancer with beautiful curly locks and tanned skin. Turns out he had previously been in the Coast Guard and was working on a private boat for a family that had just returned from several months at sea/land in the Caribbean. He admits that he is 31 and has not had sex since he left because he had so many obligations for this rich family.

First bad idea, we head to the beach. It is windy. My dress is now around my waist, tits out the top and my panties around my ankles. Bodies contorted…. a few too many drinks. We see police coming at us from down the beach. Panties up. Dress down. Read more »

45[F] Nashville Bang Gets Out of Hand

Years had passed since I had woke up drunk.

My eyes opened and all I saw was pillow. I could still taste bourbon cocktails and my mouth was kind of sore from being stretched. I fought off the urgency to head to the bathroom strategizing that a few more hours would sober me up and hopefully I would not be hung over. As I leaned over towards the nightstand to check the time on my phone, I realized I was completely nude and in a strange hotel room.

I gathered my thoughts and realized that I was on vacation away from home. I felt my feet hit a longer leg and knew I was not alone in bed. Struggling to remember, I pulled the sheet up closer to my neck and dove my face in the pillow. I knew it. I was definitely in bed with someone. Talk about sobering up – real fast!

I felt his body roll on to mine. His hand petting my hair. Meanwhile I was trying to remember what he looked like, his name and anything else. His pants and belt were on the floor. I didnt even have a piece of jewelry on. No idea where anything had landed. This was clearly not my hotel room. Read more »