A Date with Mary

I am posting a series of true stories about my encounters with "providers" around the country. This is the fifth in the series. I totally respect these women and in these stories I have no intention of demeaning them. The names of the women have been changed for their protection. Everything else is as it happened.

I was in St. Louis on business and decided it was time for some companionship. I searched some private message boards and decided on an older woman named Mary. She was a plus-size lady, but not too big. I liked her pictures and she had some great reviews. I called her number, introduced myself, and asked if she was available that evening. Luckily for me, her schedule was open. I booked her for four hours starting at 7:00 p.m. She was a little taken aback at our initial date being that long, but I assured her that I knew a great deal about her and I was excited for the opportunity to see her. She gave me her address, which turned out to be an apartment building in a suburb south of town.

As the day wore on, I was getting more excited to see Mary. At about 5:30 p.m., I showered and shaved...my face and my cock. If you've read any of my other stories, you know that I love being a "smoothie". I knew that Mary was of a like mind. The evening promised to be fun. Boy, is that an understatement!

I allowed myself plenty of time to negotiate traffic and I arrived at her high rise apartment building with time to spare. I was about ten minutes early, so I waited in the parking lot, the anticipation rising. The anticipation was not the only thing rising. I got to the lobby and at exactly 7:00 p.m. and punched in the numbers for her apartment. I a few seconds, a sexy voice answered. I identified myself and she buzzed me in. Her apartment was on the third floor. I got to the door and knocked softly. The door opened. She was behind the door, but I heard her say, "Come on in."

I entered the apartment, she quietly shut the door, and before me stood a lovely lady. I knew that she was in her '50s which was perfect for me. I'm 65. I weigh about 170 and she probably weighed a bit more than that. Perfect for my tastes. The apartment was dimly lit and as my eyes adjusted, I saw Mary standing there in a satin robe with the sash untied. I could clearly see about half of her large breasts and my gaze traveled southward, I saw her womanly stomach beneath which was her smooth pussy. My dick was already stirring. I put the donation envelope on an end table, ready to play.

Mary came forward and embraced me. The embrace was followed immediately by a long, deep, tongue-filled kiss. Yikes! What an introduction.

I moved my right arm around her and my hand grabbed her ass. In a flash, the robe was gone and she was there in all her glory. Obviously, there was going to be no get-to-know you chatter!

My cock was rigid as Mary reached for my belt, undid it, and skinned down my pants and under pants in one smooth motion. My shirt followed and I kicked off my shoes. She bent down and took off my socks. I was now totally naked and I hadn't been in her apartment for two minutes. Maybe one.

As she finished with my socks, my cock was right in her face, so she kissed the tip and stuck my 6" about half way in her mouth for just a few seconds. She then stood up and we began a series of deep, long kisses. I fondled her ass and moved my right hand around to caress her smooth, sopping pussy.

"Do you want a sample of what's about to happen?" Who was I to refuse the appetizer even though I didn't know what it was?

I said, "Serve away, madam."

She turned her back to me, moved to the arm of a sturdy chair, put her hands on the chair's arm, bent over, spread her legs and said, "Give me you cock, now!"

We're still five minutes into our date and I'm about to stick my hard cock in her hot pussy. Unbelievable!

I took a step forward and grabbed my cock. The alignment was perfect and my cock slid straight into her throbbing womanhood. I said, "This isn't going to last long."

She growled, "Harder and faster."

In about 30 seconds, I shot three big blasts of my cum inside her. No condom, no worries.

She shivered, turned around, squatted down, and took my shriveling cock in her mouth. "Did we get it all?"

I said, "Yes, my dear. We got all of it for this round, but there will be much more to come." Or, cum.

She hugged me again as I felt her leaking pussy. Some of my cum dripped on the floor, but I got a good sample in my hand. I put my finger in her mouth and she licked it clean. I reached back down to her pussy to collect another sample. "Your turn," she said.

Being a polite guy, I licked up my own cum. "Yummy!"

So, here we are standing right by her apartment door, naked, and freshly fucked. She gave me a quick kiss and said, "Follow me."

She sat on her couch and I noticed that she had placed a towel there to sit on. I sat in a chair to her right. The conversation then proceeded for a few minutes just like any normal chit chat between two people who had just met. Except, we were both naked. Plus, my cum was leaking out of her and onto the towel.

She told me a little about herself and I did likewise. She was a widow and her two kids were grown up and long gone from her house, but they lived in the St. Louis area.

By then, my heart rate had returned to normal. She told me that the next course was in her bedroom. I stood, offered her my hand, and we moved down the hall to her bedroom. Actually, we were in the guest room which she had dubbed her Play Room. There was a medium-sized flat screen TV on the dresser. There was a video playing. As I looked carefully, it was a video of her and another woman on a boat, probably on a lake. Obviously, someone else had been present to do the filming. Mary was on her back on a chaise lounger and the other woman was going down on her. Clearly, she's bi!

Mary pulled back the covers on the bed in the Play Room and we laid down. I was still recovering from the "welcome" I got at the front door, so we cuddled up and had a chat. We each gave a Reader's Digest version of our life's journey. She thought mine was pretty fascinating, mainly since I'm technically homeless. I'm on the road 100% of the time and don't own a house or rent an apartment.

Keep in mind that we were about 30 minutes into a four-hour date. What did she have in mind next?

As we continued to chat, Mary slowly moved her hand down my chest. She fiddled with my chest hairs and then slowly worked her way down to my crotch. There weren't any pubic hairs for her to play with, so she started teasing my cock. I was a bit surprised that it started to respond, slowly coming to life again.

We continued to talk and I asked her what I could do for her. I told her that the usual pattern when a guy meets an escort is that he's mainly concerned about his own orgasms. I told her that I loved giving orgasms. That got her attention.

She said, "I have a confession for you. I am a squirter! If you get me to a full orgasm, you'll get a gusher."

I was intrigued and my cock hardened even more. I'd seen pornos of squirters, but I've never witnessed one in person. I said, "Let's do it."

She looked me in the eye and said, "This is supposed to be about you and your pleasure."

I said, "My pleasure would be getting you to cum and to squirt. I can get off seeing a woman get off."

She was lightly holding my cock and it was stiffening. "See what I mean?"

I leaned in the kiss her. I think the discussion of my getting her to squirt really turned her on. The kissing became passionate, even desperate. Clearly, she wanted me to get her to squirt. My impression was that most guys she sees did not understand that Mary really likes to cum.

While we were kissing, I moved my right hand to her breast. Both her nipples were that hardest I'd ever witnessed. I quickly got the impression that it wasn't going to take much to get her off. The deep kissing continued and I moved my hand down to her pussy. It was absolutely soaked! At first, I thought she had already squirted, but as I was to find out, her definition of squirting and mine were quite different.

I put one and then two fingers into her vagina. It occurred to me that I might be able to fist her, but that would be for later. With two fingers inside her and my thumb working her clit, she started to tense up. I was anxious to see how this would play out. I doubled down on working her pussy and clit. Her breathing became deeper and her pussy was clenching my fingers. I lowered my head and started lightly chewing on the nipple. That did it! She threw her head back, stiffened her whole body, and squirted. I'd never seen such a thing. I increased the pace of fingering her clit. My hand was soaked, but I wanted to see how far I could push her. All of a sudden, she held her breath, her face turned red, and it was like somebody turned on a fire hose. A gusher blew out of her hot pussy a distance of a couple of feet. She was holding her breath with her back arched. For a split second, I thought she had passed out. It was extremely erotic. Fortunately, she knew from experience to put two towels on the bed. They were soaked. I don't know if her ejaculate was pee or some kind of woman juice, of which I was unaware. Anyway, she was gasping for air while a little more fluid leaked out.

Slowly, she came back to earth. Her body went limp and she actually had tears in her eyes. She looked over at me and apologized.

I said, "What are you apologizing for? That was the most erotic thing I have seen in a long time." My cock was, I think, the hardest it's ever been.

Mary was slowly recovering and, again, she started to apologize. It put my finger on her lips and said, "Shhhh." We were a mess, but I put my arms around her and we cuddled for a few minutes in silence.

Eventually, she was returning to normal. Then she went back to her theme of this being about me instead of her. I chuckled and said, "My dear, this was the absolute coolest thing I've ever been a part of. I am flabbergasted that a woman can do that and I'm thrilled that I get to have a ring side seat, so to speak."

We were now on our sides facing each other. She said, "In a little bit, I'll be all recovered and then you can fuck me again."

I swear my dick got even harder, but I said, "How about if we make love, instead of fuck?"

She tossed the towels on the floor and we settled in each other's arms. Her breathing and pulse rate had returned to normal and we laid there in silence. I think she might have drifted off to nap for a few minutes. My mind was going a thousand miles an hour. I think we stayed in that position for about half an hour.

Eventually, we got off the bed and took turns in the bathroom. She had freshened up, fluffed up her hair, and gone back to lie on the bed. I went into the bathroom and thought I had to pee, but my cock was still hard from what I had just experienced. I splashed water on my face, took a swig of the mouthwash, and went back to the Play Room. Mary was now on her side, facing the wall. She was out cold.

I got into bed and carefully lay beside her, spooning her while softly wrapping my arm around her midsection. I wanted to let her nap for a bit. Actually, I dozed off myself. When I awoke, about a half hour had passed. She was stirring and rolled over on her other side, facing me. Again, she started to apologize, but I put my finger on her lips.

She excused herself and headed for the bathroom. When she had returned, she had run her fingers thru her hair and, I think, washed her face and crotch. She was ready for the next round.

She cuddled up to me and we chatted more about life. I asked her why she did what she did, reminding her that I was glad she did this. She said that the plain fact is that she just can't get enough sex. She absolutely feels the best when she's having an orgasm. I told her that I think she set a new standard for orgasms. She poked me in the ribs, laughed softly, and suggested that we test that hypothesis. Who am I to argue with a naked woman laying in my arms?

I suggested that I wanted to try something. She didn't even question me. "Go for it."

When we were coming from the living room to the Play Room, I noticed her laptop on the dining room table. I said, "You've got a Mac laptop and probably have QuickTime Player on it. Let's record what happens next."

She looked at me quizzically and thought a few seconds. "Let's do it."

I retrieved the laptop, fired up QTP, and put it on the dresser beside the bed. I started recording what was about to happen.

She was laying on her back. I moved to the bed and assumed the position at her side. I rolled her over a bit and started to kiss her softly. She put her arms around me and returned the kiss with a bit more passion. My right hand slowly moved to her right breast and lightly pinched her distended nipple. She moaned and tightened her hug. I fingered her pussy. One, two, and then three fingers. She was soaking wet. I pulled back from the kiss and asked, "Have you ever been fisted?"

A look of concern crossed her face and she shook her head side to side. "Are you interested in having me try?"

She hesitated a second and said, "I think so." I assured her that at any point all she had to do was tell me to stop and we were instantly done. I would not proceed without her assent. I told her that I totally respect her limits and I had no intention of hurting her. I told her that I had never done it, but I had read about how to do it. "We're both virgins." She smiled.

At this point, Mary hesitated a bit. I'm sure she was mulling over what was about to happen. She looked me in the eyes, grinned a bit, and said, "There's lube in the top drawer of the dresser."

Almost instantly, I was blessed with another hard-on. I can't remember the last time I had three erections in the span of three hours. But, who cares, I had another one now!

I retrieved the bottle of Astroglide and returned to the bed. I laid it by her on the bed, got between her legs, and moved up to kiss her some more. Once again, the kisses got longer and deeper. It was getting very intense. "Are you ready?" She just nodded her head. Again, I reminded her to stop me at any time.

I slowly kissed my way down her body, pausing to anoint each nipple, and then slid down so that most of my body was off the foot of the bed. I stopped at her pussy and began kissing and slurping up her juices. She was moaning quietly. She pulled on the back of my head to encourage more licking. I answered her wishes for another minute or two. Then I stopped.

I got up on my knees between her legs and grabbed the bottle of Astroglide. I put a liberal amount of the slippery stuff on my right hand. I looked up to meet her gaze. She just nodded her head.

I opened her legs wide, and formed my right fist with all the fingers together in a point. I applied more lube and slowly moved down to her pussy. I placed my fingers at the opening of her womanhood and gently moved forward. I looked at Mary and she had a somewhat worried expression on her face. One more time I told her to stop me at any point. "Here we go...."

I had failed to notice that Mary had a small decorative pillow on her nightstand. She reached over with her left hand and grabbed it. I didn't know why, but I was soon to realize that she anticipated what might happen.

At this point, I rotated my hand slowly and began entering her pussy. More lube. A very slow advance. More lube. Now, I had all my fingers inside. I looked at her. "OK?" She nodded.

I continued inching forward slowly. The maximum size of my hand was now about to enter her beautiful pussy. Since I didn't have any experience with this, I didn't know what I was going to encounter once my fist was fully inserted. Her pussy muscles were stretched to the max and my fist moved the last few inches.

It was almost like there was a "plop" when my fist got inside her. I had no idea what to do then. She was squirming a bit, but didn't exhibit any signs of wanting to stop. I don't know what the anatomical terms are, but as soon as I was inside her up to wrist, she seemed to relax a little.

She moaned, "Oh my god, that feels unbelievable."

I moved forward a tiny distance and encountered something inside of her. I was a bit denser tissue than the inside of her pussy. Then my study of anatomy came rushing back. It was her cervix! I carefully felt around the outside to the "tube". She said she couldn't feel anything other than she felt stretched out due to my fist.

It occurred to me that the cervix was probably not designed to be fondled during sex, so I just curled up my fingers and left it alone.

However, the curling action seemed to trigger something in Mary. She said, "Don't move your hand. Just stay still."

I stopped all motion and tried to make my fist as small as possible. I waited a few seconds. I was looking at her clit, which was standing up. I took my left hand and spit on my index finger. There was no other motion by either of us. I placed my index finger on her clit and stroked it softly. Well, all hell broke loose. She grabbed the little pillow and chomped down on a corner, her stomach muscles contracted violently. The result was that my hand was, literally, expelled from inside her followed by a massive blast of cum and, probably, urine. As she told me later, it was the mother of all climaxes and squirts.

Fortunately, we had plenty of towels on the bed and they had become soaked. She even caught me in the chest with one last blast of whatever it was that came gushing out of her. As we discussed later, her chomping down on the pillow probably kept the neighbors from calling the cops and reporting a murder in progress!

At the time, I wasn't even aware of my cock since all of my efforts were focused on Mary. I looked down and I was almost scared. It was as hard as it can get. An angry red in color. I know that if I so much as touched it, it would shoot my third load of the day.

Mary was coming back to earth and I slowly moved off the bed and went to the bathroom. My cock was still like a rock. I washed my hands and face and returned to be bedroom.

Mary was laying on the bed with a beautiful smile on her face. "I can't believe what just happened. That was the most intense feeling of my life. Part of it was like giving birth and the other part was like glimpsing Heaven.

I said, "After what just happened, I don't think either one of us is going to Heaven."

I went back to the bathroom and got a couple more towels and washrags. I ran the washrags under hot water and headed back to her Play Room.

I got on the bed and gently washed her crotch and the area surrounding it. I moved up with the other warm rag and cleaned off her face. I patted her dry and moved up to give her a gentle kiss. She said, "I'm speechless. I've read about fisting, but I never thought it could be like this. It's not something I would do routinely, but it's something I want to do again down the road. Thank you."

I gave her a smooch and said, "You're welcome, my dear. We both experienced something new."

I then realized that I was still sporting a boner that was demanding attention. She glanced at it, but I could tell by the look on her face that she was nowhere near being able to help me out. I said, "I'll take care of this." And smiled.

I grabbed the Astroglide and laid down beside Mary. I squirted some in my right hand and immediately went to work on my cock. It was on my stomach. I grabbed it and started stroking. I could immediately feel my balls wanting to release. Just a few more stokes and I Iet fly with four or five blasts of cum. The first one landed just short of my chin. It was probably a personal record for cumshot distance.

We were both shot. It was now about 11:00 p.m. Mary invited me to stay overnight, but she gave me a fake stern look and said, "No hanky panky." We both broke up laughing.