A Second Helping of MILF

This stories starts at the airport and picks up on a previous rendezvous with an older woman whom I have not spoken of yet. She and I met at the bar and lounge area of a hotel on South Beach. I had gone there with a couple of the usual friends and we were just checking out a different scene. While we were there, we saw a group of older women who were just having drinks and enjoying themselves. There were 4 of them and 3 were incredible looking, even though the plastic surgery was a little obvious for some.

For those that do not know, let me clarify something. If you have ever thought of experiencing the fun that a woman 10 to 20 years your elder for men in their 20s, I would highly recommend it. There are several reasons, but the two that are most obvious are these: 1. These women do not play games. They do not say things they do not mean and they do not have time to figure out if you meant what you said. The few that I have been with are just fine with my wants and only wanted me to tell them what it was that I desired. 2. They know exactly what they want and will let you know it. In my experience, they are straightforward and quite capable of looking after themselves.  If any cougars or MILFs are reading this, do not think that you can also “teach young men some new things”. In my experience, this is a bunch of crap. I have been taught things by younger and older women and have been the teacher as well. It just depends upon the sexual exploration that the girl has done or is willing to try, not necessarily her age.

Like most men, I have friends that are comfortable with all sorts of women and friends that are comfortable with only one sort of woman. Needless to say, I was not able to spend a bunch of time speaking with that group of women and figuring out which one wanted something that night, next week, or sometime in the future. I had only about an hour before we left so when I saw one of the 3 hot ones walk past the bar and to the restroom, I went to the bar to wait for her to come out. When she came out, I spoke with her as she passed me and learned she also was attracted to me. She was only 38, Spanish, divorced and had one child of 16. She and her friends were celebrating the birthday of one of the group so I was not able to speak with her for a long time, but she did leave her number. This was on a Friday night during the Spring.

The rest of the night did not go very well as far as speaking with other girls at the bars and one dance club, but that is how it goes some times. My friends and I ended up talking mostly about school and some things we heard on the news. A few conversations were about future plans after school. It was a decent night, highlighted by one of my friends walking in on a male on male blowjob in the bathroom.

On Sunday, during the afternoon NFL games, I gave the MILF a call just to chat. I was intending on setting something up for later in the week, but she was very much into having something that night. She had been out shopping and was going to nap and then make dinner. She invited me over after dinner, when her daughter would leave to go study at a friend’s house and we could go from there.

To many reading this, the above statement may seem highly unlikely, and in many instances it would be. But if you are the type of person that says no way, understand this, there has been much made of the cougar and MILF movements over the past few years by the media but this market is still widely untapped as women move into their late 30s and early 40s, many of them divorce, and most want to enjoy life. If you doubt me, fine, but you should try it yourself in a large city preferably one that is a destination city such as Miami.

I went over around 8:00pm, just to be sure I did not run into the daughter. She met me at the door, wearing relaxed clothing almost like pajamas but not quite. We had some wine and talked about my plans for school and beyond. She was making small talk to ensure that I was as ambitious as she thought and smart enough to hold a conversation should she want to have one. We then began talking about her ex-husband and why she and he had separated 5 years earlier. She told me about her friends and even talked about a wild party she once attended that had several “swinger type activities” in various rooms though the party was never meant for that. This lead to a conversation about ourselves and what each of us wanted physically. It is very refreshing to have such a candid conversation with a woman. We then kissed and went into her bedroom.

She was good and got everything she wanted from me, including a couple of orgasms. I showered after the two sessions and left. I did not call her a while after that, mostly because the two times I sent her a text message she was out of town the first time and going on a date with a man her age the second. The second time did not piss me off that she was dating or make me jealous of the man she was going with. She is an old enough woman and can do as she pleases. I would be lying if I did not say I was bothered by it, simply because if she was in the mood to get some play on most other nights, I did not understand why she did call me. I know that it was either because I was not everything she had imagined or because she had just wanted a one-time deal from me. Either way, I was not getting any from someone that I enjoyed even though I was available, and that upset me some.

But you can’t let something stay with you; get over it and move one. Besides, there are plenty of women I can find that want more than just one night with me, so I went back on the hunt. I had not thought about her much since the end of the Spring semester nor all throughout the summer as I was travelling for work. I got back that fall and got ready for more school, doing many of the same things I had been doing during the Spring. That Thanksgiving, I scheduled a flight back home for the holidays to see my family. When I left, I had a layover in Tampa. From there, I was going back home. I got off the plane in Tampa and walked over to my gate. The gate was already very crowded since everyone was travelling for the holidays. I chose a spot on the floor looking towards the gate. I looked around and noticed a familiar face, but I could not quite place it.

I soon remembered where I had seen the face, in many of the pictures at the home of the MILF. I was looking at her daughter. Within a minute of the recognition, her mother came over and sat down on the seat next to her that she had been saving. She did not once look at me. It was the most awkward recognition I have ever had. I did not think our last meeting ended on bad terms, though I was pretty sure she was through with me after that one meeting. It was just a eerie coincidence that she happened to be on the same flight as I was. Of course she was on the same flight, she had said she was from a small town in Wisconsin or Minnesota. I could not remember which. She was going to see her family for the holidays.

I looked constantly at her, but I did not want to draw the attention of any of the other people in the airport so I pulled out my book and opened it and tried to read it. Of course I could not help but looking up at her every few minutes, but I thought I was being smooth. I now know I was not as subtle as I thought since she noticed me. As if just to tease me, she placed her bag in her lap, and pulled up her skirt slightly so that it came up over her knees. I looked down, to avoid suspicion, but I looked back up a few minutes later. As I was looking at her, I noticed she spread her knees apart just about an inch, giving me a tease to see part of her inner thigh. I smiled to myself as I went back to my book.

I looked again a third time, and she spread her knees again. I looked at her face, but she was staring out the window of the airport, waiting on the plane. We had another hour before boarding, so I guess she wanted to pass some time by teasing me because she spread them again, ever so slightly.

This continued for a bit, with me trying to bury my concentration in my book but not being able to and looking up at her and she would spread her legs just a bit more, revealing a little more inner thigh and ever closer to showing her panties. The whole situation was very exciting and very strange as I never once saw her looking over at me or even acknowledge me so perhaps she was simply relaxing and I was seeing something more than was actually there.

All of the sudden, the gate agent came over the loud speaker and announced that our plane was nearly cleaned and ready for boarding, so the first groups to board should gather near the gate. In the course of watching or imagining my private peep show, the plane had arrived, the passengers disembarked, and the plane cleaned without me noticing one person.

I was one of the middle groups to board, so when I got up to walk towards the gate, Veronica remained seated with her daughter, looking out the airport window. I did not try to acknowledge her or look in her direction as I passed, figuring if she wanted to see me and smile, she had ample opportunity prior to that to do so. I boarded the plane, found my seat, and sat down.

The plane was not particularly crowded as several empty seats remained with only two more groups to board the plane. I packed my bag in the overhead bin and grabbed my book and sat down. I watched the remaining passengers board the plane and noticed when Veronica and her daughter walked down. I expected that they would continue to walk past me and that Veronica would at least glance at me when she walked by, but no such luck. Instead, she grabbed a seat across the aisle from me and her daughter sat in front of me next to an elderly gentleman.

I stared down into my book, avoiding looking at her because now I was sure she did not want to see me. Her daughter leaned across and asked about sitting next to her and Veronica responded that when the plane was departing the airport and up in the air that they could probably sit closer to one another if the daughter still wanted. I figured this would be the best solution, that the daughter would sit next to her mother, putting herself between Veronica and me. I could get off the plane without looking at her again. 

The plane took off without incident and soon we were on our way north towards Washington DC with the sun having set long ago. I slid in my seat during the climb to be closer to the window. The chime came on and the fasten seatbelt sign flashed off. I believe the daughter looked back at her mother, but instead of the daughter getting up and moving next to her mother, the mother moved into my row! Right next to me!

I looked back at her row and noticed that another woman had sat down in the aisle seat so it was either sit three wide and be crammed in a large, mostly empty plane or sit two wide in each row and have plenty of room. This meant that they would not sit next to one another, but it’s not as if she were going to ask another passenger to switch seats with her in a mostly empty plane.

So Veronica was now sitting next to me with an empty seat between us. I was trying to stare down into my book but I had to say something. I looked up and she was looking at me. She smiled at me and I smiled back. To say that I was confused would be an understatement. I said hello, but I was careful not to give any indication that I knew her on account of her daughter. She was as relaxed as ever..

So we chatted, just as if we had just met and no one knew the difference. By the time the drink cart had come around most of those around us had gone to sleep, including Veronica’s daughter. She checked by leaning forward to ask her something but she did not respond, so Veronica stood up from her seat to check and her daughter’s head was slumped down as she slept.

Veronica sat back in her seat and pushed up her arm rest and then slid closer to me. She looked at me and barely above a whisper asked, “so, did you enjoy my show?”

I smiled devilishly and replied, “absolutely.”

“Good, because I was hoping you would.”

“Anything else you want to show me?” I said grinning as she giggled.

“Well I would but I can’t here.”

“Well I have one idea.” And with that, I reached down and pulled out her jacket from her bags handles. It was cold where we were going so it was smart of her to carry it with her on the plane. It was also very fortunate for what I had just thought of.

I pulled the jacket over her lap and up to her belly, pulling it up so that it was just underneath her breasts. It was a long jacket so it fell plenty far down over her knees and half way down her legs. I then, with one hand pushed one of her legs towards the aisle and then pushed the other towards the window so they were nice and spread. I then lifted her skirt towards her waist for easy access and slowly moved my hand towards her pussy.

I looked at her face and she bit her bottom lip, smiled, and closed her eyes. I then rubbed the center slowly, on the outside of the fabric. Next, I pulled one end of the sides of the pants over towards the other side, exposing part of her pussy. I then touched and tapped on it lightly. She leaned over and whispered, “damn you are sexy. Such a naughty boy.” To which I replied, “go to the restroom and take these off.”

I removed my hand, placed the fabric back over, she closed her legs, put her jacket down, and walked to the bathroom. It seemed like she took an eternity there, I even thought that she might rub herself while she was there. She finally returned and held one of the sides out her purse to show me. I then put the jacket back where it had been, she spread her legs quickly and grabbed her arm rests, and I pulled up her skirt.

This time to tease her, I licked the tips of my middle and pointer finger and slowly moved them under the coat and onto her warm flesh. She was back in ecstasy. I tapped and caressed for a minute and then rubbed her hood. With her eyes closed, she smiled widely. I then forced my middle finger into her center and flicked her clit with my thumb. Her breath quickened momentarily. I continued doing this for a few minutes and went back to rubbing. I then brought my hand out and licked my finger tips again. This time I rubbed much more firmly and she began to stiffen her body as she reached climaxing.

I tapped slightly again, and then rubbed the tip of her clit. Finally, I stroked the hood up and down and did not stop rubbing or stroking it for two minutes. I had to slow down considerably as she clamped her thighs together and grabbed my knee and squeezed. I was happy there was a coat there because I had gotten a very stiff boner for the length of the touching. She finally relaxed and I removed my hand. I looked at her and smiled. She slowly opened her eyes, smiled, and whispered, “best public sex ever.”

She then reached into her purse on the floor, and put her pants on each leg and pulled them over her knees. She then pulled them up as far as she could without arching her back, but keeping the jacket covering her lap. Finally, she leaned away from me, pulling one side over her hips and I was flashed one side of her cheek. She then put the jacket over her other side and leaned into me to pull that side up. Afterwards, she used her jacket as a blanket and slept the remainder of the trip.

I simply allowed myself to calm down and went back to reading my book with the biggest smile on my face. I woke her just before landing and she slid back to the aisle seat and did not move to wake her daughter, opting for the plane to do that as we touched down. When it was time to disembark, she stood in the aisle with her bag and purse, and without looking at me, waved at me behind the seat. I have never tried to contact her since.

How a Stripper Parties

Lorenzo grew up in Southern California and attended a small school not far from home. His best friend from home, Matt (not his real name to protect the guilty), went to UNLV for a few reasons, among them to party. Lorenzo would often go to see his friend in Las Vegas and party with him. After college, Matt got a job in hospitality management in Las Vegas and has stayed there since then. It so happens that Lorenzo would still go visit Matt while we were in graduate school together. On one occasion, I was invited to go with Lorenzo to Vegas because up to that time, I had never been.

We flew Southwest out of Fort Lauderdale and arrived just before sunset on Friday evening. By the time we landed, we were already tipsy. We then took a cab to the hotel where Matt worked. He got us a deal using his discounts and we had to pay some nominal fee for taxes and whatever. After unpacking, Lorenzo and I went to dinner. Afterwards, we went back to the room to get ready for the night. We ended going to a few other clubs in other hotels along the strip, which was pretty fun. We had a good enough time, but nothing was special about what we did. Matt was busy that night but would be able to hang out with us all day on Saturday and Sunday. So no big deal on Friday night.

Saturday morning, we woke up late and went for some greasy food to fight the hangovers. Afterwards, we hit up the pools. If there is something that is a site in Las Vegas that does not get nearly enough attention, it is the pools. The parties are amazing. The women were everywhere. Most were right around college age to late 20s. All were drinking, and most looked amazing in those swimsuits. I wish I had brought a real camera instead of my phone camera because the pictures I took did not do the girls justice. There was music, plenty of activity, and of course jager-bombs.

We met a group that was in town for a bachelorette party. One of the group was the bride, her sister was the matron of honor, and the rest were friends from school, home, or cousins. Lorenzo was very interested in the matron of honor. She was not into him. I was talking to one of the friends from college. A cute little blonde with great thighs and bubble ass, which is of course, perfect. Matt came over to join us as soon as he could and offered to get the group some shots when he arrived. We talked for a bit longer with them, but the girls had to go to keep to their arranged bachelorette party schedule dutifully prepared by the matron of honor. So the blonde and I exchanged numbers.

Afterwards, we went back upstairs to change and shower. Matt abused his managerial privileges and got us a bottle of vodka on the house for us to drink as we got ready. Remember when you were younger and you watched cartoons and some part of the story allowed one of the characters to take advantage of the situation and you knew this because the character would rub his hands together and little devil horns grew out of the top of his head? That is almost exactly what happened to me. Matt was going to use his position to get us free drinks for much of the night and I was going to take full advantage of that. I devised a quick plan that if we ran into the group of girls, I would be sure to be near Matt so that I could get them feeling good without any cost to us.

We then agreed to sleep or gamble for about an hour after getting ready and going out that night. Vegas is like Miami in that people don't really go out to clubs and bars until close to midnight and with dinner around 7:30pm, we could not drink so much as to be wasted before we went out. We were not under any schedule since this night we were going to stay at the clubs and bars at our hotel with Matt. We had quick bite, then we changed and went down stairs to the lobby. We each had one drink together there and then went into the casino to gamble a bit. I lost about $250 in 30 minutes and quit. That was fast enough for me. Lorenzo, however, is great at craps and spent a few hours there. I think he ended up barely ahead but he had been several thousand dollars ahead at a time when I would have surely quit. I told him I was heading to one of the bars, and I found Matt there already, chatting with two girls. So much for the nap after dinner, it was game time now.

We stayed there a while before heading to the dance club. There, we saw the group from the bachelorette party. I immediately went to chat with the blonde, but she sort of blew me off. She was much more interested in her drunk friend than anything I could offer at that exact moment. I was not alone, since Matt was with me. This was the trump card and Matt, again, abused his position to get the group a free bottle of champagne. The kicker was that the bottle came out with a sparkler on top, which was not new to me having seen this in Miami all the time, but was a shock to that group. Thank you Midwest. The blonde was so thankful for Matt’s help, and by extension my help.

It was also not that late, being just after 1:00am, and she told me to text her later to see where she would be. That group left and we were again alone. Lorenzo came to join us and we stuck around, chatting with more girls and having some fun grinding with random girls.

After 2:30am, Lorenzo was hammered beyond belief because he’s a light-weight. Matt and I decided to drag him to the room and then we would go hit up the strip club. On our way from the hotel to the strip club, I texted the blonde. She said that the group had gone to bed when the bride to be threw up. Her sister had decided to take care of her, along with one of the cousins. The rest of the girls split up either going to bed or going out for more. The blonde and one of the other college friends decided to go back out.

She asked me where we were going and I told her. The other friend had never been to a strip club but being that she was in Vegas and drunk, she decided to throw caution to the wind which was perfect. We arrived at the strip club and let them know where to go once inside. I had to text her while inside the bathroom because phones were permissible, but cameras were not. Once she was there, we all had a few drinks and a round of shots and we were ready for some fun. The girls were talking to the strippers and we ended up negotiating on a lap dance for her newbie friend. The blonde and I would get to watch as the stripper gave the blonde a lap dance. Matt ended up getting a lap dance of his own and that was the last I saw of him for the rest of the night as his stripper dragged him off to another room.

In our room, the stripper was dancing all over the friend who was loving it. Now, no matter what anyone tells you, girls are always allowed to touch the strippers. I don’t mean she just touched her ass or get tits in her face and touched them. I mean the stripper was naked and the friend reached out to touch her pussy. I was amazed. Additionally, the blonde that was with me began to imitate the stripper on me and since she was not employed by this establishment, I was able to touch her as I pleased. It was so good, I asked for another lap dance and got the four of us a round of shots.

The friend receiving the lap dance had so much fun, she wanted another, but I was finished with purchasing them so I declined. It was probably for the best because the friend’s eyes were glazed over and I doubt she remembers anything about that experience. On our way out of the club, the friend threw her hands in the air and declared that she “wanted to come here more often and party how a stripper parties.” We three got into a cab and headed back for our hotel.

On the way home, the friend leaned against the window and passed out. I started making out with the blonde and we enjoyed some heavy petting and touching. Once we arrived at the hotel, I carried the drunk friend back to her room and it was fortunate for me that the blonde and she were sharing a room together because we got right to it once the friend was put in the bed. We had to be silent, but we made enough noise during the action to wake a sober person up. Let me tell you that the blonde’s ass was as much fun as I imagined it would be and she was very willing to go for two rounds. The first time I finished finished on her back with her on her knees. The second ended in her mouth with her laying down on the bed and me standing over her from the floor because she did not want to make a mess the same as the first. It seems I am not as good of a shot as I thought I was.

The second time was better because it actually started after the first with the blonde hoping in the shower to wash the spunk off. I jumped in with her and she got on her knees to show her appreciation for the champagne earlier. She sucked very well and was in love with my cock. Swallowing was no problem for her. I was only able to stay and sleep in the room for a bit after that and had to go to my room as the sun came up. The blonde did not want to look like a whore in front of her friend. I thought that we should have done something to the friend, just because she wanted to party like a stripper, but she was passed out and the blonde didn't want to be a bitch.

Either way, that first trip to Vegas was memorable and fun. I hope that any trips there in the future are just as fun.

I Don’t Normally Do This Sort of Thing

This story starts out innocently enough as a random happen chance discussion. It was a typical Friday night and my friends and I had gone to South Beach to his up some of the bars. We had decided to stay away from the large clubs simply because it was going to be too expensive for us to go there and it was late in the academic year and most of us had spent much of our money. Unlike a few of our friends, we did not have trust funds. Though, the one of our friends who did was always good to purchase a bottle or two for us when we went down to South Beach.

We stayed at one of the bars for quite a while, just pounding beers and pitchers until we were drunk. We decided on a quick round of shots before we left to go to the next place to hold us over for the cab ride. We got to our bar and Lorenzo was hungry. Instead of heading straight in, he and I walked down the street a block or so to a pizza place to grab a quick bite before going back to the bar where all our friends were.

When we got back to the bar, it was extremely crowded and it took a while to push through the crowd. We had a bunch of mixed drinks and shots, trying to get the buzz back after having eaten. Lorenzo and I started talking to a group of three friends who were undergrads at another school. Two of them were cute but fairly stupid. I have no idea why some men find stupid women attractive. It completely turns me off. So I began ignoring them but still standing there with Lorenzo because he was very much into one of the three. I excused myself to the bathroom. When I came back, they were no longer there.

At some point later in the night, the DJ had turned the music up and started playing rap music from the early 1990s which makes college girls just want to dance. Lorenzo stood up in a booth on the other side of the room and was grinding with the girl he had been talking to. It would have ended like any other typical night with him getting her number and going from there except by the second song, he was really starting to sweat. Now it was warm in there because the front door was wide open, it was very crowded, and so many people were moving, but it was not that hot. We all discovered why he was sweating so much during the next song as Lorenzo doubled over with his hands on his knees and puked on this girls legs and shoes.

She screamed and the crowd all said “ewww” at the exact same moment. Just after that, as I was walking towards him to get his drunk ass up and out of the bar, the bouncers picked him up by his limbs and carried him out, tossing him into the street. I followed them and helped him off the concrete and hailed a cab. We were lucky there were no cops near there because he probably would have been arrested. We got in the cab and went home. Halfway home he wanted to go back but I tried in vain to explain why would could not hang out with those girls for the rest of the night. You will need to commit this name memory. I call her “puke legs” because she appears in a few more stories since Miami is kind of a really big small town.

I dropped Lorenzo at the front door of his apartment. I had no intention of helping him get into bed or out of his puke covered shirt. I got him home and he had to figure the rest out for himself. I went home, mad that my night was ended so I jumped online to look at a few pron sites and rub one out.

It just so happened that when I got home I had forgotten that I had left my computer on when we left so my skype and chat programs were still online. I opened one of the sites to get started but before I could do anything a woman sent me a chat message asking what and how I was doing while we were out. Now if this sounds strange, itis because it absolutely is. I probably could have gone back out there, but I was not going to pay for another cab ride from my apartment nor was I going to drive out there to fight for parking at midnight. If you don’t know Miami Beach, then you have no idea how bad parking can really be.

Now on to why it was strange but entirely real.The reason I had this woman, Donna, on my messenger was simple, I moved down to Miami without very much furniture. When I had time after moving in, I browsed craigslist for furniture and found someone selling a bunch of used, fairly cheap furniture. Her son had moved away for college and while there, he met a girl and got her pregnant. He married her and was living with her and their new baby in an apartment while going to college in the northeast. He had plenty of furniture from his first two years of college and combined with hers, enough to live. So Donna was selling his old furniture, much of which was in storage, for him and giving him the money for the child. Since I bought so much from her over the course of two months, I added her to my contacts, to communicate faster and not rely on leaving her voice mails because she never answered her phone to screen her calls from her ex-husband. So there you go.

Donna asked me how my night had been and I gave her the quick cliffnotes version. To my surprise she was still on. She told me she had gone to dinner with friends and was home now, but not tired enough to go to bed. She asked me what I was doing and I simply told her I was just browsing the net. She, however of the shrewd kind, correctly guessed that I was actually doing something else because it was a Friday night at 11:00pm. She asked if I was on a dirty website. I let her know that she had deduced correctly. She then began to question why I was staying in noting the time and day.

“So why aren’t you going back out and meeting your friends?”

“I’m not really wanting to spend the money on cab rides back out”

“You could go to the bars in Coral Gables”

“Yea not really interested in going by myself”

“Well staying at home and looking at porno sites is not the right way to spend a Friday night”

“You got me there”

“If I were you, I would go somewhere at least. You are in school, you should have fun”

“Yea you’re right about that” “but why are you still at home then”

“Most of the men my age are not interested in a woman their age, they want a woman your age. My ex-husband did, left me for his secretary”

“Oh I didn’t know”

“It’s no problem, I do miss the company sometimes like tonight”

“Yea I could see that” “And you don’t date around or anything”

“I was seeing someone, but that ended” “Now it’s just me and my toys”

It was at this point that I got interested. I had been checking out some videos so I was sporting a chub but I was not doing anything else because of this conversation. The woman had been nice to me about the furniture and I had gotten much from her. We had mentioned porn and dirty websites already, so I decided to throw a line out there to see how she responded. If it went well, I would go further but if not, I would sign out and get back to what I had intended.

“LOL nice! Have you had the toys a while now?”

Immediately, I regretted the question. This was too far. There was no way this could go over well. I should have used a much more conservative approach. I was really nervous about her response because I had been crass and too forward. Then again, maybe I hadn’t.

"I got my first one about 5 years ago. I’m not dead. I am only 43 and still active"

“Nice Im sure that they are very fun”

“It always is with me, but it would be nice to get something real”

At this point, I did not know what to say, in fact I just let her go for a while and did not speak to her as I was trying to find some better videos than what I had been seeing. They were decent enough girls, the action just was just bland. I reviewed our conversation at that point and decided to compliment her as a sort of gesture of kindness, though she was in great shape for 43 years old.

“Bet you are a whole bunch of fun, which is too bad now”

“What do you mean too bad?”

SH*T! My compliment had crashed, I needed to recover.

“Sorry I just mean that it is too bad for me because you look great for 43”

“Thank you. You are very sexy yourself, but I would have never been able to tell you” “Whoa this wine is making me hot”

That’s right, blame the wine. Blame whatever you want. I was a shark and I smelled blood in the water.

“Id love to see that”

“I’ll bet you would”

“Yea I could even help with the toys”

“That would be nice”

“Yea much better than porn because a real woman is always better”

“You are a schmoozer, but I like it”

“So no dates for you recently”

“No, like I said just me and the toys”

“Would be nice to have someone do that for you”

“Yes it would”

“I could help you”

“No, I don’t think that is a good idea”

“Why not? I am well into my 20s and I have been with older women before”

“Well I don’t think I would want to meet someone who I met on the internet” “That’s dangerous you know”

“Yea it probably is but we have met in person”

“That’s true”

“And more than once so I am certain you are trustworthy”

“Thank you” “Still, I’m not sure I would be comfortable”

Damn, I was losing the opportunity. I knew now that one of two things would happen. First, it would go nowhere and it would take forever, if ever, for us to speak again because the conversation would be so awkward. Maybe she could be very mature about all of this, but I would feel weird. Second, this would happen and we would never speak again. I was going for broke and decided to lay it out there.

“We could just hang out and if you did not want anything it would be no problem and I would just leave”

“You’d just come over?”

“Yea I remember where you live” “If you wanted me to leave you could say so” “We don’t have to do anything”

“I do have a movie from Netflix and was going to watch that” “Some company would be nice”

I was in. This was going to happen as long as I was very slow with her, it was going to happen. Best ending possible to what started out as a bad night. I left shortly after that, I called her once I was a few minutes from leaving my apartment so that I did not sound too excited. She said she would be ready with the movie, which I had no intention of watching.

I called her after I parked my car and shut off the lights about ten minutes later and called just to make sure she was still awake and comfortable with me being there. I parked down the street so that I would not raise suspicion and so that I would not be blocked in if I needed to leave. I guess I feared her neighbors were performing a neighborhood watch or something at midnight. Stupid.

I knocked at the door and she answered wearing some sort of workout or yoga pants and a sweatshirt. Donna obviously did not want to give off the vibe that she was looking to get some play, but come on. Who was she kidding? She had already told me about a wild college life and her toys so the fun, college girl inside did not go away, just changed methods. She offered me a beer or wine and I asked for a beer to seem nonchalant. She had already poured her wine and the DVD menu was up on screen. She seemed a bit on edge, so I was not going to be too forward.

I sat on one side of the couch close to an arm rest so I could lean against it. She sat in the middle and pulled a blanket over her legs and put them on the couch. She grabbed a remote and pressed play. It was some movie about the JFK assassination. I was not really all that interested, but had to fake it.

“So is this a documentary or a depiction of what happened?”

“It’s a drama. It has this guy and that guy and this other guy all in it. I have been wanting to see it for a while now."

Wonderful, she is into the movie. She leans back and to my side a little. I lean to the back of the sofa so that we are not as far apart as we had been, but still not very close. She turns to me to ask me if I am into conspiracies and so forth. I told her that I was into history but I did not like it when dramatic depictions glossed over the actual events to make them more to Hollyowood’s liking. She agreed finished her wine. I was fresh out of moves. We had been talking about her toys and now we were discussing a freaking movie? I had to do something. I asked her if she needed a refill because I did and that I needed to go the bathroom.

She showed me the bathroom and I took a minute to figure out my next move. I figured she would be on the couch waiting and I knew that she trusted me because we had gone through 30 minutes of the movie without talking very much. When I came back out, she was on the couch with her head against the back of the sofa. I went into the kitchen and grabbed another beer and thought of a plan. I walked back over to the couch and sat on the same side as before, this time much closer to the center and her.

She pressed play and the movie started back up. I asked her if she was into JFK and she told me she watched a bunch of documentaries on the assassination a while back. I asked her if she knew much of him and she could only repeat things about Jacky Kennedy, Bobby Kennedy, and Marilyn Monroe. I reminded her about the cabinet of Camelot, the Cuban Missile Crisis, and his love life. She lit up remembering that she had heard those things before.

“JFK was something of a playboy. Women loved him and he loved them.” I said.

“Well he was very sexy, especially since he was president.” She replied, smiling and looking at me.

I knew this was the time so I leaned in for a kiss. She looked at me for a second and I paused, but then she smile and she accepted. We started kissing quite a bunch and I was well on my way.

I leaned over towards her even more, trying to get her to lay back. It took some scooting into her, but eventually she leaned back. I threw the blanket on the floor and continued. I started to feel her legs and hips, but deliberately taking my time. She started to rub parts of my body as well and then began unbuttoning my shirt. I sat up and took that off and we continued for a few more moments until I suggested we go to her bed.

She complied and turned off the TV and movie. I laid down and she took off her sweatshirt revealing a t-shirt underneath. We continued what we had been doing for a bit more and then I moved to take off my belt and pants. She looked at me and watched me as I did it slowly. When I was finished undoing them, about to slide them off she looked at me and said,” I don’t normally do this sort of thing.”

Yeah right. In college you did and like I said, that person she was did not go away.

I was going to respond that I didn’t either, but she would see right through that. Instead, I said we could stop but she said she did not want to. I think she meant that she didn’t do that sort of thing anymore as she had to stop in college once she got pregnant, but there was no such thing stopping her now. “It’s just that you’re so sexy and I have needed it for a while.”

We continued in a slow but methodical way. I asked her to show me some of her toys and she brought out a couple of dildos and other things. She was already naked so I grabbed one of the dongs. I used it on her as she grabbed the rails of her head board and moaned. After that, I climbed up to the head board and put my dick in her mouth. She sucked for a while, then I went back to using the dildo on her. I then climbed to the foot of the bed to put my cock inside her. She lifter her legs and hips and spread her cheeks to get me to give her anal. After that, she sucked on my cock a little more. The night went well with her getting a very nicely covered chin at the end.

The strangest thing about all of this was that she was not willing to have straight intercourse. We could only do oral, use her toys, have some anal sex, though her ass was not that great. I gave her a good session, and she left plenty of fluid on her sheets from me rubbing and licking her vagina. I hoped that she would give me any more furniture I asked for, but after that night, she never responded to an email or phone call again.

Until this was written, the only two who ever knew we met for this was Donna and myself. I did not even tell Lorenzo to brag the next morning figuring an interlude starting from chatting would be too unbelievable.