Adventures with Dolores

I've had a huge crush on one of my coworkers for the past few years. Her name is Dolores. She is 49 and a mother of three so she definitely qualifies as a MILF. Dolores is a little over five feet tall and is very slim with short brown hair. Her breasts are very small, my guess would be 34A, maybe B. My favorite part of her body is definitely her ass. It also helps that I think she wears a thong every day. She couldn't be more perfect, an older woman who liked to wear sexy panties. Plus she was single.

However I am only 29 and also married so I never made a move on Dolores. Sure we've flirted and joked around but never anything serious. I doubt she had any idea that she was my number one jerk off fantasy. Rare was the day at work I didn't ended up beating off in the bathroom while thinking about fucking Dolores or having her suck my six inch dick. Usually I would catch a glimpse of her thong and it wouldn't take long for my cock to turn into a raging hard-on.

This is the story of how our relationship changed from work friends to lovers...

Dolores stopped by my office in the morning with some work questions. However she caught me off guard when she asked something else.

Nick, do you know of any good adult stores around?

What are you looking for?

I'm not sure, I was thinking about getting one of my girlfriends some gag gifts for her 50th birthday party and that came to mind, do you think it's a good idea?

Oh yeah, they have tons of stuff that would be great gag gifts. There is actually a good place a few miles of the highway, I'll get you the directions.

Uh...Nick...do you think you would go with me. I'm kind of embarrassed to go by myself.

Of course I'll go with you, how about tonight after work?

Sounds great!

Dolores left my office and I started thinking about tonight. That store has everything you could imagine: sexy lingerie, sex toys, movies, magazines, even a video arcade where you could "preview" different movies. I've been there a few times and went into the booths to jerk off while watching different porno movies. I wasn't sure what was going to happen between the two of us but I thought it would at least be fun to look at some of the stuff with her.

Since we live on opposite ends of town we drove separately to the store. I could tell that Dolores was very nervous about going in the store. Once inside I led her to the right side of the store that had the toys and clothing.

First we looked at the lingerie. I pointed out some items to Dolores that I thought were very sexy. Mostly they were bra and panty sets. It didn't seem like that's what Dolores had in mind for her gift. But I was thinking how I wouldn't mind seeing Dolores wearing some of these, especially the thongs, and even more the crotchless thong I showed her.

Next we walked down the aisle with the toys. She couldn't believe how many different dildos and vibrators they had for sale. I picked up a twelve inch dildo and told Dolores how I wish I was that big. She laughed and said that she couldn't handle anything that size. We looked at lots of vibrators, dolls, anal beads, cock rings, and so many other things, but she still had not decided on the gift.

I asked if she wanted to get her friend a movie, so we wandered over there. This is when I started to get turned on. We looked through every section from the normal movies, oral, anal, gay, lesbian to some of the more obscure. Dolores picked up quite a few boxes and was checking them out. I started to get the feeling that maybe this was all new to her but that she was somewhat intrigued.

We got to the end of the movies and she asked me about the back area of the store. I told her that was the video preview area where you could go watch some of the movies. This seemed like a good chance so I asked her if she wanted to go see. To my surprise she didn't answer and just headed back there on her own.

Usually I'm too scared to go back there as there usually are a few guys waiting to hopefully share a room and have some fun together. I caught up to Dolores and pulled her into the first open booth and explained to her why I did that. I don't know if she totally listened to me as she was busy figuring out what these booths were.

Once she saw the paper towels and the trash can she knew guys came in here to jerk off. I half expected her to be grossed out and want to leave but she wasn't. She asked if we could check out some movies for a few minutes. My dick was rock hard and I was hoping that I would get a chance with Dolores.

I offered the chair to Dolores so she could sit and enjoy and I would just lean against the back wall, but she invited me to sit down. Then she sat down on my lap. There was no doubt she could tell I was fully erect at this time. I slid a couple of one dollar bills into the slot and the movie came on.

The first thing we saw was a young man sucking another guy's dick. Obviously the last guy in here enjoyed watching this. Dolores seemed to enjoy watching the two guys together as she had a smile and seemed glued to the screen. Not really my interest so I reached over and started turning the channels. This particular place has a little over 100 movies on a time so there is a very wide selection and I wanted to give Dolores a wide variety.

We were in the gay section as I flipped up through the channels stopping every so often to let Dolores watch some hot young men sucking, fucking, or cumming. She really enjoyed this but still didn't say anything to me. I was enjoying Dolores more than the movies as I thought my dick was going to explode in my pants.

Are you enjoying these movies?

Oh my god! I can't get enough. I didn't think I would ever get turned on watching two men going at it but I love it. And you seem to be enjoying it too.

And as she said that she wiggled her ass acknowledging that she could feel my cock through my pants. I kept flipping the channels to get out of the gay section and next was the lesbian section. I've never been a huge fan, I do love to see the girls kissing and fondling but I get very bored of watching them eat pussy and play with dildos forever. So I kept going, stopping a few times when I did see some real hot girls.

The next few sections only had a couple of channels and I don't stop here often if I'm by myself. There's some soft porn, bondage, anal, and other freaky shit that I don't care to watch. After these we come back to channel one. The first few channels are for feature films that are usually nothing else besides one on one fucking. I enjoy some of these as they do have the best looking actors.

Dolores and I watched one of these for a few minutes. There was a gorgeous girl giving head to an average looking man. Of course his cock looked to be about ten inches long which led to the following exchange.

I wish my dick was that long.

Are you sure it isn't, I think I can feel every inch of it against my ass.

If you want I can pull it out and prove it to you?

And right as I said that the movie turned off because our time ran out. I asked if I should put some more money in and Dolores agreed. I pulled a five out of my pocket and we resumed watching the same movie.

I flipped through a few more channels showing Dolores the wide selection of genres. There was oral, gangbang, threesomes, chicks with dicks, and then finally the one I was waiting for, MILF. This particular one had a boy who was probably 18-20 making out with an older woman, maybe even in her 50s.

This is usually my favorite channel to watch when I'm here.

Oh sure it is, are you sure you're not trying to pull something funny with me?

This is my all time favorite fantasy, I just love older woman and would do anything to be with one.

How about pulling your cock out and letting this older woman make your fantasy come true?

With that comment I knew it was on. Dolores looked back at me and I moved in for the kiss. Our tongues met each others and we kissed like we had been lovers for years. As we explored the other's mouth and tongue, my hands were ready to explore some other areas. I moved my hand to Dolores's left breast and massaged it very slowly. It was slightly bigger than I guessed. I moved on to the nipple and concentrated on making it hard and erect.

Dolores's hand moved down to the bulge in my crotch and she began rubbing my dick through my jeans. She would take her hand from my balls and trace my cock very slowly the entire six inches until she got to the head. Dolores would then give my head a few extra rubs and then work her way back down to my balls.

We stood up and I pressed Dolores against the wall, still kissing her, while also pushing my cock into her. She undid the buttons on my shirt and I helped her by removing it. I pulled my undershirt off and Dolores kissed my chest and teased my little nipples. It my turn to take her blouse off and undid the buttons very quickly revealing a sexy purple floral bra.

Her blouse fell to the floor and I reached behind her and unclasped the bra. Dolores's tits were gorgeous. My guess of 34B was not too far off, although they might be closer to an A. I rubbed them pretty hard trying to get each of the nipples excited. I lowered my head and took turns sucking on each of Dolores's tits. Her soft moans let me know that she was enjoying this.

I reached down and opened the front of Dolores's pants. It looked like she was wearing a matching pair of purple panties. I slid my hand down the front and felt her hairy bush. The lower my hand got, the wetter Dolores was. Finally my hand got to the promised land. I felt the bare skin of Dolores's pussy.

When I slid two fingers inside her pussy, Dolores let out a loud cry. I got down on my knees and pulled her pants down to her ankles with my free hand. I pulled my fingers out and grabbed her purple thong and also pulled that down to her ankles. She stepped out of her pants and thong and sat down on the chair. I pulled my pants and boxers down and revealed my throbbing dick to the MILF that I've fantasized about.

I aimed my dick right at Dolores's mouth and she had no problem with that. She opened her mouth and took the whole thing in at once. She began bobbing up and down on my cock showing me that she loved to suck dick. The sight of this older woman sucking my dick was almost too much. I was so close to cumming but I wasn't sure if I was quite ready. I did want to fuck her some before I came.

I pulled my cock out of her mouth and had Dolores stand up. I traded spots with her in the chair and motioned for her to come sit on top of me. Dolores got on my lap and I guided my dick inside her pussy. She started riding me while I kept my dick shoved in as far as I could get it. I knew I wasn't going to last much longer with Dolores humping me like this. But the breaking point was when Dolores whispered in my ear that she was cumming. I decided this was the best time for me and I unloaded my hot cum deep inside her. The two of us were both yelling and moaning as we hit our orgasms at the same time.

Dolores kept sitting on my lap as we came down from our climaxes. My dick fell out of her pussy as it softened up and as it did I watched some of my semen start trickling out. This sight was so beautiful, I had a hot older woman that I just fucked sitting on my lap with my cum oozing out of her pussy. We kissed a few more times while we sat in enjoyment of what just happened.

Dolores and I both got up and began putting out clothes back on. Before she started I begged her to allow me to keep her purple thong which she agreed to after I agreed to keep fucking her. Like she really had to talk me into that one.

Once we had all of our clothes back on we exited the booth. There was a line of three guys who must have heard us fucking. I think they were all hoping to get a piece of Dolores as well but we walked right past them, however I stopped and showed them her thong that I had in pocket.

We met up in the parking lot and after a goodbye kiss we went out separate ways, not before we promised to get together very soon for some more fun.

More adventures with Dolores to come...