After a long, hot summer of doing almost nothing but work (and the occasional visits from some FWB’s), I was looking forward to August, when my son’s football team starts practice. I help coach the team, and have always enjoyed getting out there with the kids, and teaching them the game that I love. It doesn’t hurt that quite a few of the moms are pretty damn cute, too.
One evening, I was working with one of my lineman, who had made a remarkable turn- around from the year before. This year, he had gone from where-can-I fill-him-in, to holy-crap- the-kid-became-a-stud! I was teaching him some technique while we were waiting for his mother to pick him up after practice.
I had met mom the year before, while I was going through my divorce. While I thought that she was cute, she was a bit heavier than I usually like my women, plus, she had a boyfriend that I thought he was a bit of an ass, just from some of the things that I had overheard him saying to her, and her son.
While I was talking to him, I heard this voice call out to him, and we both turned around. The sight that greeted me was quite a pleasant surprise. A woman was walking up to us in a tank top and a short pair of shorts, with a nice set of stems coming out of them.
“Hi coach. I’m sorry I’m late. I had to stay at work a little later than usual. Thanks for staying with Eric for me.” the lady said.
I must have had quite a shocked and confused look on my face, because she looked at me and said “You DO remember me, don’t you? I’m Eric’s mom, Jennie.”
“Yes, of course I remember you!” I answered. “I’m sorry. I didn’t recognize you at first.”
“Yeah, that’s what everybody says. I lost 300 lbs over the spring and summer.” she giggled.
“I’m sorry, 300 lbs.?” I asked.
“Yep. Of course 250 of that was that cheating ass of a boyfriend of mine, but 50 was all on my own.” she replied.
“Wow. Well, I’ve got to tell you, you look great! Congrats on all 300 lbs.” I told her.
“Thanks. I feel a hell of a lot better, let me tell you!” she said. “Well, we’ve got to get going. I’m hungry, and I’m sure my eating machine here is too.”
As I was packing up the rest of our gear, I watched her walk away, and was entranced with the way her ass swayed in those shorts she was wearing.”Damn,” I thought to myself, “I hope she picks him up more often!”
As the season progressed, I saw more and more of Jennie, and she looked better every time. After a scrimmage that we had against one of the local powerhouses in our area, we sat the kids down and gave them a pep talk. While I was giving my part of the rah-rah speech, I was looking around at the parents, also, who were all standing a few feet behind the team, and I noticed Jennie looking at me and smiling.
Afterwards, she came up to me and started talking to me about how her son was doing this season, and if there was anything that he could do to improve his game. I told her that Eric was doing fine, and was significantly improved over last year.
When I knew that our conversation was drawing to an end, I looked at her and said “I know that this may be inappropriate, being Eric’ s coach, and that I should probably wait until the end of the season, but, would you like to go out for a drink some time?”
To my surprise, she smiled at me and answered “I would love to. I was wondering if you were ever going to ask me.”
We decided to go out for dinner on our first date. She told me that her favorite Italian place was a little Mom-and-Pop restaurant that just happened to be about two blocks from my apartment. I told her that I have never been there, and that it sounded like a nice place to have dinner.
We decided to meet at the restaurant, since she would be dropping her kids off first. Even though I only live a couple of blocks away, I decided to drive there, just in case dinner went well, and we went some place after. I got there early, and waited in my truck, in the parking lot.
When she got there, I got out, and was immediately stopped in my tracks. Jennie got out of her car, and was wearing a short summer dress, that was low cut in the front, and a pair of sandals. The way the dress formed around her hips, her firm looking legs sticking out from the bottom, and the nice display of cleavage that the low neck line gave, I could almost feel the blood starting to rush to my dick.
They put us in a booth in a quiet corner of the place, and brought us our menus. The waitress asked if we would like a drink while we were looking over the choices, and I asked Jennie if she wanted to get a bottle of wine.
“Oh, that sounds nice, but I’ve got to warn you, I get a little dangerous when I drink wine sometimes.” she told me, with wicked little grin on her face.
“In that case, make it two bottles.” I joked with the waitress, and picked out a bottle of red that I thought Jennie would like.
Over dinner, we got to know more about each other, and she told me that she could tell that I was going through a rough time last season, because of the way that I got mad over a couple of little things, and the same things didn’t bother me at all this year. I explained that my ex hit me with the divorce one week into the practice season, and we were battling the whole season. I knew that it was affecting me, but I didn’t know that it was that obvious.
“You’ve got to remember, I’m a bartender. It’s my job to pay attention to people.” she told me. “You definitely seem more together and easy-going this year. That’s a good thing.”
As we finished dinner, and we were well into our second bottle of wine, I joked with her that I thought she seemed to be handling her wine pretty well.
“I didn’t say that I couldn’t handle wine,” she answered, “I said that I get dangerous when I drink wine. The question is, will you be able to handle me?”
I took that as a challenge, and smiled at her. “I guess we’re just going to have to find out, aren’t we?” I told her.
“Oh, you think you’re man enough, huh?” she asked, as the waitress came to the table. “We’ll have another bottle, please.” Jennie told the girl, as she gave me her wicked grin again.
“Oh, damn,” I thought to myself, “I better buckle up. This could be a wild ride!”
By the time we finished the third bottle, we were both pretty buzzed, and feeling damn good. I paid the bill, and as we walked out, the owner came up to us and asked if we wanted him to call a taxi for us.
“That’s ok, I just live a block away. I told him.
“Isn’t that convenient,” Jennie asked, “No wonder you agreed to this place so easily. You thought you would get me drunk, and take me back to your place.”
“You’re the one who ordered the third bottle of wine.” I reminded her.
“Yeah, I did, didn’t I?” she giggled.
We decided that we would walk back to my place, to walk off dinner, and because the cops in my town have no sense of humor when it comes to drinking and driving. Being popped for a DUI would not be a good way to end a first date!
While we were walking, or stumbling, home, we talked a little more, and I helped support her by putting my arm around her shoulder. When we got to my place, I brought her in and locked the door. As I turned around, she was standing there with a funny look in her eyes.
“I want you to understand something, before either of us gets ant wrong ideas,” she told me. “I’m not looking for a serious relationship. I”m not ready for one right now. I like you, and I like the way we get along, and that we talk, but I’m not ready for a committed relationship. I’m drunk, and I’m as horny as hell right now, but if you’re looking for anything more than some fun, tell me now.”
“I think we’re going to get along just fine,” I smiled at her, “I’ve only been divorced a year. I’m not ready for anything serious right now, either.”
“Good. Then we understand each other.” she said softly, as she walked up to me and pushed me back into my recliner. “Now, let’s have some fun, while we’re both still good and drunk.”
With that, she sat in my lap, wrapped her arms around my neck, and pulled me in for a kiss. A long, hot, wet kiss that seemed to last for an hour. “Holy shit!” I thought, “If she kisses like this, I can’t wait to see what else she can do with her mouth!”
I didn’t have to wait very long to find out. The kissing turned into petting before too long, which turned into outright groping. Soon enough. She slid off of my lap onto the floor, and positioned herself between my legs.
“I hope you don’t mind, but I’ve got to see what’s been poking my in the back of my leg for the past few minutes.” she told me, as she started to undo my pants, and pull them off.
“Oh, ok, if you have to.” I joked.
As she pulled my boxers off, she took a hold of my now stiff cock, and said “Oh, yeah. I’m gonna have fun with this!” as she started to kiss and lick the head.
While she was licking my cock, I took my shirt off, and she then got up on her knees, and lowered her head all the way down over my dick and started to slowly suck on it.
“Oh, my god!” I exclaimed as she started to suck a bit more firmly.
“Mmm,” she said, as she stroked my hard cock. “I like to give head, so you’d better just sit back and enjoy. I’m going to be here for a while. It’s been a while since I’ve tasted some cum.”
“Ok,” I told her, “but I’ve got to tell you, very few women have ever been able to get me off from giving me head.”
“Oh, good. I like a challenge. Now be quiet, relax and enjoy. I’ve going to have some fun now.” she responded.
She proceeded to give me some of the best cock-sucking that I’ve ever had. She truly enjoyed giving head, and it showed. She would suck on my stiff, hard cock for a while, then she would lick and kiss her way up and down the length of the shaft, stroking it.
After a while, she took my hands, and brought them to her head. I took the hint and grabbed a hold of a handful of her hair, and started bobbing her head up and down on me. She really started going nuts on me then, and sucked with even more enthusiasm and firmness.
It didn’t take too much more of this fervor to start that feeling, just before the point-of-no- return. “Oh, damn, you’re going to make me cum.” I told her.
“Um-hum,” was her only response, and she went even faster and tried taking my cock as deep as she could, playing with my balls as she did.
“Oh FUCK!!!” I cried, as I felt my cum surging out from my balls, all the way up the shaft of my cock, and squirt into her mouth.
It felt so good, that my legs were shaking, and the tip of my prick was so sensitive at that point, that I had to pull her off of it.
“Did you like that?” she asked.
“You have to ask me that? I would think that big load I just shot down your throat would have answered that question!” I answered.
“Just making sure,” she said, “I enjoyed that too. You’re tasty!”
“Yeah? Well, as soon as I can walk, I’m going to see just how tasty YOU are.” I told her.
“Well, I’m looking forward to that. It’s been a long time since someone went down on me without my having to beg for it.” she said.
“You’ve just been hanging with the wrong crowd.”
“Apparently!”
She stood up off of the floor, and climbed back into my lap. We started kissing again, and I let my hands roam all over her legs, softly and slowly, eventually sliding up under her dress. As I went higher up her thighs, she sighed, and slowly opened her legs, giving me more access. I could feel the heat radiating from her crotch, and as I let my fingers lightly graze over her panties, I could feel the moistness seeping out.
“See, I told you I enjoyed that as much as you did.” she told me as she pulled her lips away from mine for a moment.
“Well, why don’t we get more comfortable, and we can both enjoy my pleasing you.” I told her, as I stood her up, got out of the chair, and directed her towards my bedroom.
When we got to my bed, I pulled her in and gave her a deep soul kiss, as I slowly undid the zipper on the back of her dress. I stood back and let the dress slip down off of her shoulders, down over her hips, and watched as it pooled around her ankles on the floor.
I knelt down, and kissed and licked her belly and legs as I lifted her feet and removed the dress completely. The little strappy wedge sandals looked so cute, especially with the red nail polish on her toes, that I decided to leave them on. I slowly kissed my way up her legs, lightly grazing her panty covered pussy with my nose, and blowing on it, and worked my way back up. I let my tongue play at her belly-button for a second, and progressed up further, grazing her tits and now stiff nipples as I stood all the way up, and kissed her full on the mouth again.
She moaned, and pulled me in closer, as my hands were sliding up and down her back. My right hand reached down to her panty-covered ass, and pulled it in close. She was wearing a pair of lace boy shorts, and with her full, firm ass, they looked, and felt, fantastic.
As I was pulling her ass in to my crotch, I could feel my cock starting to rise again. I slowly started working my way around to her ears, ans started nibbling and licking her ears, and just below, on her neck. When I got to that little hollow, just below her ear, and slightly in front, I planted a firm kiss, and lightly sucked on it. When I did this, she gasped, and started to go slightly limp. I seem to have found a sensitive spot!
I kept working my way around her neck, and down, taking my time, savoring every bit of flesh. While I was working my way down her chest, towards her still covered breasts, she reached down and took a hold of my rising cock.
“No,” I told her, “this is all for your pleasure.”
“But I did get pleasure, feeling your thick hard cock in my mouth.” she replied.
“Right. You had your desert. Now it’s my turn.”
She sighed, and let go. I resumed working my way down her chest, and came to her bra. She was wearing a light, lacy bra that matched her panties, and held up what looked like an impressive pair of tits hidden behind it. As I was kissing and licking the exposed tops of her breasts, I reached around and felt for the clasp.
When I finally got the clasp undone, she let out another sigh, and I could see her breasts sag a bit under their weight. As I kept kissing and licking my way around the ever-increasing exposed flesh of her tits, her bra eventually fell off.
“I’m sorry that they’re not as firm as they used to be,” she said, “After I lost all that excess weight, they just won’t firm back up!”
“Hush,” I told her,”they’re beautiful, and I’m going to enjoy every bit of them.”
I went back up to her lips, and kissed her, as my hands took hold of her full tits, and felt the weight of those beauties. There may have been some sag to them, but they DID look and feel great!
After kissing her and gently squeezing her tits for a couple of minutes, I bent down, and took one tit in my hand, and lifted it to my mouth. I gave it a kiss just above the nipple, and slowly licked my way around her areola, never quite getting to her hard, stiff nipple.
“Oh, god, that feels nice.” she whispered.
That was when I reached out my tongue, and let it lightly slide over the very tip of her nipple.
She gasped when I did that, and pulled my head in tight. “Oh, damn, don’t tease me like that. It’s been too long.” she told me.
While I was kissing and sucking on that nipple, I was teasing and playing with the other breast and nipple. I switched sides after a couple of minutes, and started to work on the other one with my mouth, my hands gently squeezing and pulling on the wet one that my mouth just left
After a few more minutes, I took both tits in my hands, and pushed them together, getting the nipples to touch. I bent back down, and licked both nipples at the same time, and took both in to my mouth at once, and sucked on both of them.
“Oh my GOD!” she cried, as she tried to pull my head in even tighter.
“You like that?” I asked, as I straightened up.
“God, yes. I felt little butterflies in my stomach when you did that. It felt wonderful.”
“Good. Let’s see what else I can do to make you feel wonderful.”
I started working my way back down her belly, and when I knelt down and tickled her belly-button again with my tongue, she gasped again, and I felt her stomach muscles contract.
“That tickles!” she giggled, and I kept going lower, until I reached her panties. I started to go lower, this time licking a trail on the lace, until I reached her pussy. By now, her panties were soaked, and I could smell and feel the arousal being emitted from her pussy.
I slowly reached up to her hips, and started to pull the panties down. When I got them down to her ankles, I repeated what I did with her dress, and lifted one foot at a time, and removed the panties.
I then started to slowly kiss my way up her legs, first one side, and then the other, until I reached the tops of her thighs. I then slowly reached up, put my hand on her chest, right between her breasts, and gave her a gentle push down to the bed.
As she hit the bed, I took a hold of her legs, and pulled her forward, so that her ass-cheeks were just at the edge of the mattress. Then I spread her legs apart, and started kissing my way up the inner parts of her thighs. When I got to the top of one side, I went back to the other side. Jennie was breathing harder now, and she too hold of my head, and said “You like to tease, don’t you?”
“I don’t know WHAT you’re talking about!” I joked, and resumed the teasing. She let out a moan of frustration, and I asked her “You got a problem wit dat? I can always stop, if you don’t like it.”
“No, no! Don’t do that! I’ll keep quiet!” she said.
I laughed and told her, “You don’t have to keep quiet. I like to know that I m doing what you like. Just don’t complain!”
“Ok, no more complaining! Please go back to what you were doing!”
“Well, I don’t know if I can remember where I was. I may just have to start all over again.” I teased.
“NO!” she cried out, “Here, I’ll show you where you were.” and took hold of my head.
“No,” I told her, removing her hands from my head, “SHOW me where I was.”
“OOH!” she whimpered, and put her hands onto her pussy lips. “Right here. You were right here.” she told me, as she started stroking her labia.
I followed her fingers with my tongue, as she stroked herself, and she led me to her clit. At that point, I pulled away, placed my flattened tongue at the bottom of her now dripping wet pussy, and slowly licked my way up, stopping to lick around her wet opening, and stick my tongue as far in to her as I could, which caused the loudest gasp yet.
“Oh, god, please lick my pussy! PLEASE eat me!” she cried.
I slowly went back to licking my way up her slit, and when I got to her hard clit, sticking out a good half-inch or more, I gave it a long, slow lick, up and down, on both sides.
“Oh my god!” she cried, and started moving her hips around, trying to get my tongue everywhere at once.
When she finally realized that I was going to control this part, she relaxed, and let me go to work on her. I went back to her clit, and licked all around it, top, bottom left, and right. I finally pressed my face into her, took her clit lightly but firmly between my lips, and started to suck it in and out, while I placed a finger at the soaking wet opening of her pussy, and slowly slid it in.
“Oh, yes!” she exclaimed, as my finger went deeper, and I applied a little more pressure on my sucking of her clit. When I found that little ridge inside her hot, wet opening, I started to stroke it, and went to town on her clit, releasing it, but licking it faster and faster, then clamping down and sucking on it again.
“Yeah, yeah, YES!” she yelled out, as I slid a second finger into her, and felt her muscles clamp down on both fingers, juices running out.
As she was coming down, I licked softer and slower, until I felt her relax completely. Then I stood up, her juices covering my face, and placed the head of my re-hardened cock at her wet opening, and applied a little pressure, and slid my cock all over her wetness, coating my cock with her juices.
Finally, I put the head back at her opening, and slowly pushed it in, savoring the hot, wet, feeling, as I went deeper and deeper, until I bottomed out, my balls rubbing against her ass- cheeks.
“Don’t move,” she told me, “I want to get used to your thickness first.”
So I stood there for a minute, feeling her warmth and wetness covering my cock, until I felt her moving her hips around.
“Oh, yeah. Now I’m ready.” she said, and started moving her hips faster, and in circles. “Fuck me. I want to feel that thick cock of yours sliding in and out. FUCK ME!”
I started to slowly slide my thickness in and out of her wet hole, sometimes teasing her by only slipping the head back in, and then backing out again.
“Stop teasing me and fuck me, damn it! I want to feel you pound my pussy. I need a good pussy pounding right now!” she told me, with a wild look in her eyes.
And so I did. Still standing at the edge of the bed, holding her legs up with my shoulders, I took her by the hips, and started to slam into her pussy. I could feel the juices running out of her, covering my balls, and could hear the squishing sound her pussy made as I fucked her harder and faster. Her tits were also bouncing around, all over the place, creating quite a scene.
“Oh, yeah. Fuck me. Fuck me. FuckmefuckmefuckMEEEEEE!!!!!!!!!!!!” she yelled as I tried to give exactly what she wanted. I could see her eyes roll back into her head, and she started to quiver, so I held on, as she shook.
When she was done, I pulled out, and she moaned. When she saw that I hadn t cum yet, though, she smiled and cheered up.
“Move back,” I told her, “let me get on the bed.”
“How about I move, you get on the bed, and I get on you?” she asked. “I love to ride, and you’ve got a dick MADE for riding!”
Not being one to argue with a woman who knows what she wants, I climbed on the bed, and lay on my back. She got back on the bed, took my stiff, hard cock in her hand, and bent down to kiss it. She took a long lick, smacked her lips, and said “Hmmm, I taste pretty good!”
“Yes, you do.” I told her, as she straddled me, and, still holding my cock, lowered herself onto me. We both moaned at the same time, as she dropped all the way down onto me.
“Oh, DAMN, this feels SO good!” she said as she humped and wiggled all over me.
After a couple of minutes like that, she slowed down, drew her lags up, and told me “I’ve got to fuck you now.” and started to raise and lower herself on my cock, which I could see was shiny with her juices.
Then she put one hand between her legs, and started to rub her clit, and play with it.
“Oh shit, I’m going to cum again!” she cried out, and dropped her pussy all the way down on to my cock, and rubbed her clit, until she yelled out “YES!!!”, and I could feel her pussy convulse around my thickness filling her up.
“You still haven’t cum?” she asked.
“After that blow job you gave me earlier, it may take me a while.” I told her.
“Oh, yeah.” was her only response.
“How do you want it next?” I asked, as she started to slump down on me.
“I want to feel you in me from behind.” she answered.
“Oh, yeah.” I said, thinking that I will finally get to see her ass bounce around while I am fucking her.
I got around behind her, as she climbed off of me, and got on her knees. I pushed her down on to her belly, and climbed on. “What are you doing?” she asked.
“I want to do you this way.” I told her, as I slipped my shiny wet cock into her shiny wet pussy.
“OH YES!” she cried out, as I buried myself into her from that position, straddling her ass. “God damn, that feels good!” she said, as I started to fuck her. “Oh shit, you’re hitting places I’ve never felt!” she told me, as she started humping her ass back at me.
“Fuck me! Please fuck me good. This feels SO GOOD!” she cried, as I started to fuck her faster.
At one point, I pulled out, grabbed a pillow, and slid it under her hips, elevating them. Then I slipped back into her, only to hear “Ohmygodthatfeelsgood!!!”, and she started wiggling and humping back even more.
After a few minutes of this, sliding almost all the way out, and then back in, pulling out, and slamming back in, fucking slow and soft, then fast and hard, I saw her asshole winking up at me, so I moistened my thumb with her juices, placed it at her pink hole, and started to slide it in.
“Oh god, what are you doing? That feels so good!” she exclaimed, so I buried my thumb all the way, along with my cock, filling her as best I could, and bumping into her with my pelvis.
This seemed to set her off again, and she started to shake again. “OH MY GOD! I’M CUMMING AGAIN!!!” She yelled, and slammed her hips back at me, as I felt her juices explode out at me.
When she came down again, I knew I wasn t going to last much longer, so I asked her where she wanted me to cum.
“On my tits.” she told me. “I love the feel of hot cum on my tits!”
When I knew it was that time, I pulled out, and she immediately rolled over and pushed her tits together. “C’mon baby. Shoot it right here.” she ordered, as I stroked my pussy-slicked cock.
It didn’t take long, and I felt that feeling deep down in my balls. “Oh yessssssss.” I yelled, as my cum squirted all over her big tits. I couldn’t believe how much I had to shoot, considering I had already cum once!
“Oh, yeah!” Jennie said, smiling at me as she rubbed my juices into her skin.
Later, as we were laying in bed, after we caught our breath, Jennie looked up at me and asked, “So, do you believe in this whole ‘friends with benefits’ thing? Because I can see this friendship being VERY beneficial!”