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Staying at The Holiday Inn

As i travel alot, my job had me staying overnight in a city about an hour and a half away from my home. I checked in at the Holiday Inn and the desk clerk seemed to have a computer problem with my reservation. So, she called on a coworker to help her with my check-in. The coworker appeared from a room behind the desk and I immediately noticed her cute face and deep voice. Her name tag said Jane and she seemed like she was about 45 years old, which would have made her about 12 years younger than me. She had a great smile and was very sweet as she apologized for the delay. But more important, she knew how to resolve the issue and soon I was receiving my room key.

I dropped my bags in my room and went to dinner and stayed at the restaurant bar for a few drinks. I came back to the hotel and went to my room. Within 5 minutes, the hotel fire alarm went off and I found myself and the other residents heading outside at 10 PM at night. They said someone overcooked a bag of microwave popcorn in one of the rooms and when the fire company arrived, we were heading back inside within 5 minutes. As I went in the lobby, I noticed Jane was apologizing to all the residents as they filed passed her heading back to their rooms. I kiddingly asked her “Are you the designated apology person for Holiday Inn?” She laughed and said “No, I just want all the guests to enjoy their stay here.” We small talked a bit and I liked her short 5 foot frame and black, wavy hair. I noticed that her ring finger was empty, so I asked her if she would like to join me for dinner when I am back next week? She said she would like to, except the hotel policy states she couldn’t date people that stayed at the hotel. Thinking quickly and looking at her cute face, I said no problem. I will stay at the Hampton Inn down the street next week. She smiled and said “that will work” and we exchanged phone numbers.

The week passed , so I was back in town and texted her the day I was checking in and asked if she still wanted to meet for dinner. To my surprise, she said “Yes, I have been counting on it.” So we met at the restaurant that I visited the week before and our cars pulled in next to each other. We exchanged smiles through our car windows before we both got out to meet. Gone was her Holiday Inn issued uniform and business jacket and it was replaced by a very nice fitting red dress, which stopped 6 inches above her knees, revealing a great pair of legs. She was short in stature, but the dress revealed the large breasts that the Holiday Inn jacket kept concealed. I went to give her a hug and upon the release, she moved for a quick kiss on my lips. We both smiled and went into the restaurant and took our seats at a table. We talked about various things as we got to know each other, sipping wine as we enjoyed each other’s company. My eyes wandered often down to her cleavage, which the red dress accentuated very well. She told me she was married once, but got divorced 10 years ago. She said she then dated a guy and was engaged for two years. However, it broke off 4 years earlier when she caught him in bed with her neighbor at the time. She said she was traumatized and has not been with a man or dated in the 4 years since. However, she said she knew she had to get back into the swing of things again and I just seemed like a nice guy when we met at the hotel lobby. That made my night for sure!

Dinner ended and I coyly asked her if she ever wanted to check out a competitor hotel? She smiled and said “sure”, all the while knowing I was inviting her to my room. We both drove to the Hampton and proceeded to head to the room that I checked into earlier that evening. I let her go first through the door to the lobby which allowed me to check out her very shapely ass and the back of those great legs. As we got in the elevator alone, we kissed and let our tongues dance a bit. I told her that she was a great kisser and she responded by saying “In my 60 years of life, at least I learned how to kiss right.”

WOW! This lady that I thought was 45 was actually 60, but she rocked the hell out of that red dress and her voice and smile could take me anywhere. We got to my room and when we entered, I told her that I had a bottle of wine and a six pack of beer if she wanted something to drink. I usually travel with both beverages so that I have a choice depending on my mood on a given night. She chose the wine and we were both soon sipping wine from hotel water glasses. I started to kiss her again and soon my hands were feeling the shape of her hips through the material of the red dress. I started to kiss her neck and trailed up to her ears, taking a lobe in my mouth and letting my teeth nibble just a bit. She gasped and then pushed me away and said there is something she has to say. She told me that she is very nervous because it has been so long since she has been fucked and she needs me to be very slow and gentle with her, or she just couldn’t go any farther tonight. I assured her that we will go as slow as she liked and that my intention is to have us enjoy each other, not have any uncomfortableness. She nodded her head in agreement and said softly “I trust you.”

I helped her unzip her dress and she unbuttoned my dress shirt and soon we were standing in front of each other, me in my boxers and her in her matching bra and panties. The bra was being filled out by two of the nicest breasts I have ever been that close to and her panties were stretched by her wide hips and shapely ass. I said to her “are you sure you are 60?”, as her body was so enticing. She said “oh yes, and I hope it can still please you like a woman should.” I moved us to the bed and we once again let our mouths meet, our tongues dance. My hands caressed her body and I felt her breasts pressed against my naked chest. I felt my cock start to grow inside my boxers and it was pressing against the front of her panties. I moved my hands behind her back and undid the bra clips, unleashing the sweetest mass of mammarys I ever felt before. Her nipples were not large, but my mouth wanted to suck them bad. I moved my face from kissing her lips slowly down her neck and chest until one of those pointy nubs was covered by my mouth. I could tell by her moans and squirms that they were very sensitive and my tongue began to lick and circle. Meanwhile, my hands were now squeezing her ass cheeks through the material of her panties, before I slipped a few fingers under them and into her ass crack. I pulled myself up off the bed and removed my underwear, revealing my wide, but average length cock. I started to help her out of her panties as she laid on the bed when she got a glance of my manhood. She said “Oh my god, you are so thick. Please make sure that I am ready for you before you do anything. I don’t want any pain from your width.” I said “Babe, I will take my time and make sure you have no pain.”

I laid her on her back and spread her legs wide apart, revealing her trimmed, but not shaved pussy. It was a very small slit and her lips were almost non existent. She noticed the look on my face and told me “I have always been very small and tight and some guys that are not gentle will hurt me. Sometimes, if the guy didn’t care about how he hurt me, it would hurt for days, so much that I had to call out from work.” I told her “I understand Jane and I only want to pleasure you, not give you any pain. I will be gentle and you tell me if you want to stop.” She nodded her head in trust and agreement.

I moved my face between her soft thighs and I started kissing her slit. My tongue pressed into her, trying to separate her folds. She was not only small and tight, but she was very dry, which I wasn’t sure was about her age or her level of excitement. My mouth licked up and down the slit and I drew up as much saliva as I could to get her as wet as possible. I knew that if I ever wanted to feel my cock inside of her, I was going to have to get her very, very wet, one way or another. I remembered wine and beer, but never even gave a thought to bringing lube. As my face was buried into her easing folds, my hands wrapped under her thighs and grabbed her ass to pull her tight against my mouth. My one finger went between her ass crack and found her button-like asshole. She immediately said “my asshole is for pooping only. Please don’t do that anymore.” I stopped quickly, never wanting to violate her trust. My concentration was totally on her pussy and getting her to the point where she would allow my cock to penetrate her.

Her clit began to enlarge a bit as my tongue worked it over and over. I never felt such a tight pussy even with my tongue and I knew I had to get her moaning and enjoying the attention. I eased my index finger into her and felt her walls press it tightly. My saliva now had her pretty wet and my beard was covered in my own spit, but her droplets were starting to flow as well. I eased in a second finger and she gasped in pain a bit. I said “it’s ok babe. We will take this very slow”. She nodded as she continued to gasp and breath harder. My two long and thick fingers were soon working her pussy as if it were an asshole of another woman that needed to be stretched a bit before anal. As I pulled my fingers out of her, I noticed that they were wet from her own juices. I moved my hand to her mouth and whispered “here babe, taste how wet you are getting. You are lubing yourself just fine and soon you will be able to take me”. She chuckled a bit and I continued to lick her clit with passion.

I felt that she was very wet and almost ready to take my cock. I got up and said “I think you are ready for me, but I need you to get me ready too.” She smiled and said in her sexy voice “I would love to suck on your cock and get it nice and wet.” I positioned the head of my dick at her mouth and her lips began to kiss it. She was slow at first, gently kissing and licking the shaft before she grabbed it at the base and took it all in her warm mouth. She sucked it like a savage and it seemed obvious that she wanted to please me as much as I wanted to please her. She had me rock hard and ready and it was time to see if my width would be accepted by her small slit.

I told her “I want to try to go in you now. We will take it very slowly and if you feel any pain, we will stop.” She said “ok, I trust you.” With that I moved her on her back again and positioned the head of my swollen cock at her wet, small folds. I pressed slowly against her and I looked down to watch me enter her. She let out an “Oh God Damn” as the head disappeared inside her. I stopped an held it there as I whispered “slowly babe, slowly babe, slowly babe”. I pressed forward a little more and she yelled again and said “this may not work.” I said “relax Jane, we are getting there. We just have to go slow. No pain babe, no pain.” I started to pull back out and then pressed back in again, not all the way, but in a method that would hopefully widen her and make her feel more relaxed. It was working and soon I was almost all the way inside her. Her face had a look of relief and I smiled and said “see, we are fine babe. I will get to pleasure you now the way you should be.” I started to pick up the pace and it seemed she was more relaxed as I did so. Every few moments I would whisper “you ok yet?” and she would smile and nod her head in approval. I never felt a pussy so tight around my cock. I have enjoyed anal with other women in the past, but nothing ever felt this tight. I was pleased that she was staying very wet and so she was loving having my cock fuck her.

As my pace picked up and I was starting to pound her like I never thought I would to a lady her age. I noticed how her huge tits were bouncing up and down, actually slapping her chin. My thrusts seemed to be guided more by how much I could get her breasts bouncing, then by how I was stretching that pussy. She gasped harder and said she was about to cum and I kept encouraging her by saying “come on babe, cum on my cock. You are taking all of me, cum for me, cum on my cock.” She screamed loud enough that I think people in the next room probably heard her. But I knew she came and that was the goal.

I picked up the pace even more and her tight pussy was getting my cum ready to shoot as well. I whispered “I am about to cum babe.” She replied “Cum in my mouth, I want to taste you.” I gave three or four more deep thrusts and then I pulled out and quickly and moved to straddle her head, my cock to her mouth. She grasped the head with her lips and her hands stroked my shaft until it exploded into her throat. She took every drop as my body tensed, until I was done and there was not one drop of my cum outside of her mouth. We fell into each other’s arms and laid together until 2 AM. She said she had to go because of having to work tomorrow and we got dressed and I walked her down to her car. She left and I went to bed.

The next day, I texted her to thank her for a great night and in hopes of doing it again on another visit. She texted back that she too enjoyed it and thanked me for being so gentle and slow with her. She then texted that she had to call off from work because her pussy was hurting too much. I offered to go and comfort her with a coffee, pain meds or anything else she may need and she said she just needed time to heal.

Three weeks later, I was back in her town again and we went to dinner and again went to my room and relived what we did the first time. We took our time again and we both came again and enjoyed the playtime.

Part of me feels sorry for her because of how scared she is of ending in bed with a guy that wouldn’t be gentle. But I was glad she trusted me enough to let me play with her and bring her the orgasms that her 60 year old sexy body deserves. I have not been back to that city in 3 years now and we have not stayed in touch. But if I ever do go back, I will stay at the Hampton Inn, but look for the lady at the Holiday Inn!

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