It was ideal. My parents lived a short commute a way, and I lived at home until I could save enough for an apartment.
Once I moved, I joined my colleagues for Friday Happy Hours near the office, and not too far from my new apartment.
It was always a good time. It was there I met Elaine. She was the head of another department, and on this particular Friday night, we were the last ones left. The others had to catch commuter trains or get home to their families. "C'mon Bret, how about a burger? They're pretty good here. I'm buying."
"Thanks, Mrs. Fielding."
"Please, Elaine, and it's Miss. I've been divorced for fifteen years. I know I'm old enough to be your mother, but I'd much prefer Elaine."
Okay. If it makes you feel better I'll call you Elaine."
It was just a burger and beer, white wine for her. She asked me about school, and stuff like that. "Bret, I'm having a good time talking to someone like you. I don't want this to end just yet. I have beer in my frig, and I live a short walk away. Can I interest you in coming home with me?"
I'd had girlfriends in high school and college, but I was still a virgin. The most I'd ever done is feel up a few of those college girls' tits. I didn't think I was naïve; it was just that I didn't think a woman Elaine's age would have any romantic interest in someone like me.
"Beer's in the frig, and there's a bottle of white wine in there, too. Open it for me, while I change into something a little more comfortable."
Like I said, I didn't think I was naïve, but I'm not sure what I thought Elaine meant when she said she wanted to get into something a little more comfortable.
The sheer negligee showed off her nice ass. I didn't say a nice ass for a woman her age. And her tits seemed still firm. I could see her nipples through the clear fabric.
We sat on the couch, and for a few minutes continued our conversation from the restaurant. Then, Elaine pulled me toward her and kissed me on the mouth, using her tongue. Her other hand was on crotch. "I'm usually not this forward, Bret, but I find you extremely attractive."
I was shocked. Like she'd said, she was almost my mom's age. Having said that, my tongue was soon engaged with hers, and as her fingers found the zipper of my pants, my hand found her tit. "Hmmmmm, Bret, your hand feels so good."
Elaine pulled down the thin straps on that negligee, and guided my hand back to her tits.
Within moments her own hand was inside my pants trying to get my cock out. "This is a little uncomfortable, let me show you my bedroom."
As we walked toward her bedroom, I was holding my pants up, but Elaine let her negligee fall to the floor. I was looking at her lovely, naked ass.
She got on the bed, and I started to get in with her. "No, you don't. I have a rule, no one gets in my bed with their clothes on."
My pants fell to my ankles, as I took my shirt off. Then I sat on the bed and took off my shoes and socks. Once my pants came off, I got back on the bed. "Nope, everything."
I still had my briefs on. I got up, turned my back and took them off, too. It wasn't that I was embarrassed; it was just that I was nervous. I'd never been in this situation before.
Immediately, Elaine's arms were around my neck, and our tongues were dueling. Her hand went to my cock, "Bret, you're already hard and it's so big."
Later in life, I was to find out that it's just about average.
I didn't know if my cock was big or not. I had nothing to compare, and Elaine was the first girl, I mean woman, to see it or touch it.
"We're going to have so much fun." She guided my hand between her legs.
Frankly, I had no idea what to do. I just let me fingers explore. Of course, I was curious.
Meanwhile, Elaine was slowly jerking me off. "Bret, it's been a long time for me, my pussy is so ready. C'mon, give it to me."
I didn't want to tell her the truth. I didn't know what to say, and I wasn't sure exactly what to do. Elaine rolled me on top of her, and then guided my cock to her pussy entrance, and then just like that I could feel my cock inside her; or at least part of my cock inside her.
Then it was over. I was so ashamed. "I have to go, I'm so sorry."
"It's okay, Bret, It happens to all men once in a while."
I was in such a hurry; I couldn't find my socks. They still might be under Elaine's bed.
I dreaded going to work on Monday. I was sure she'd tell everyone. I'd have to quit my job; move and change my name. It was a complete disaster.
Monday morning came, and the realization was that no, I couldn't quit my job, I couldn't move and I couldn't change my name. I'd just have to face the consequences.
I was certain that every woman in the elevator knew about my ineptitude. I was certain that Elaine had spent the weekend calling every woman in our company telling them what a joke I was.
Walking from the elevator to my office, my face was beet red. I was sure every woman knew and was laughing at me.
I no sooner got to my desk than my phone was ringing. "Bret, it's Elaine, I had fun Friday night. Why don't you come for dinner? I'll cook. How about Thursday?"
"Really? Are you sure?"
"I'm positive. Thursday after work, I'll meet you in the lobby."
I was in shock. I thought this was going to be the worse day of my life, and now Elaine wanted to see me again.
Thursday couldn't come soon enough. The days dragged on.
"Dinner should be in about an hour."
We were sitting on her living room couch having a drink. "Bret, about last week?"
"Ummmm, please don't remind me. It was so embarrassing."
"Oh, Bret, it happens. Now, be honest with me, and it's nothing to be ashamed of, are you a virgin?"
I turned red. No twenty-two year old guy wants to admit that. I hung my head. "Bret, look at me. There's a first time for everything. If I had known, I would have taken it slow."
She stood up, and took me by the hand. "Come with me." Just like last week, she led me to her bedroom. We were both fully dressed.
As soon as we were in the bedroom, she said, "You know my rule, no one gets in my bed with their clothes on." She started undressing.
I hesitated, but a few minutes later, we were both naked and lying in her bed. "Now, Bret, I promise I'll take it slow, and in the morning, you'll say this was the best night of your young life."
She guided my hand to her pussy, and showed me how to touch her. I didn't really put my finger inside; I just rubbed her very wet opening, then Elaine showed me where her clitoris was and how to play with it. "Yeah, Bret, just like that. Nice and slow. It's very sensitive. Ummmm, keep going, oh yeah, oh yeah, oh yeah. Yes, oh, yes."
I didn't know what a clitoris was or that women had orgasms, but Elaine had just had one. "Bret, that was so good for me. Do it just like that again."
I did and she did. "Now, it's my turn." She knelt between my legs. Of course, I was already hard. "She started stroking my cock. "I didn't realize how big it was last week." Elaine was playing with my cockhead, my balls and stroking it, slowly. "Bret, I've forgotten how hard young men get. And you have a beautiful cock."
I felt like I was going to cum soon. She must have sensed it. "Let's stop for a bit." She slid up next to me, "why don't you play with my titties?"
I started. "After what you did to my pussy, my nipples are very sensitive, be gentle."
I tried. "Ummm, just like that."
Elaine let me enjoy them for a while. One or two of the college girls I dated had bigger and firmer ones, but I never was able to spend as much time with theirs, and it was always in the dark. "I'd love you to kiss them."
"Just like that. Use your tongue. Ummmm, for your first time you're doing great, and I promise, we've only just started."
"Bret, I know you admitted you're a virgin, but I have another question for you, "have you ever had a blowjob?"
Of course, I hadn't. I'd heard guys talk about them, but I thought it was just bullshit. I couldn't imagine any girl wanting to do that. Remember, this was long before the internet and the easy available of porn.
"Ummmm," I blushed.
"I didn't think so. This is your lucky day. Elaine took my very hard cock in her hand, "and mine, too."
Then the next twenty minutes were the greatest of my young life. Elaine started by kissing my cock, then licking, and using her tongue on my balls.
By the time she actually began to suck it; it didn't take long for me to cum. "Ahhhhhh, oooooooh, aaahhhhh," I sighed.
"Bret, your cock is amazing. I'm going to want more later, but now, you rest while I get dinner on. She put a robe on, and disappeared into the kitchen.
I closed my eyes, and thought about what had just happened. It was, as I said, the greatest thing ever. Then I thought about Elaine. She didn't look bad for her age; about 5' 6" tall, her ass looked great, and I've already been introduced to her lovely titties, and then just now her amazing mouth.
Elaine said she'd want to do it again later. I was already getting hard thinking about it. Just then, "Bret, put some clothes on, dinner's ready.
Dinner was excellent, but of course, it was after dinner that you want to know about.
"Bret, I had such a good time with your cock, but now it's time to put it somewhere else besides my mouth." She stroked it. It was already hard.
"I want you to use your fingers like you did before, then I'm sure I'll be ready for your cock."
I quickly put my hand on her pussy, and used my fingers like Elaine showed me. "Slowly, Bret, slowly. That's it just like that, and right there. Yeah, right there."
Her pussy was really wet. "Ummmm, oh Bret, oh, you make me feel so good. Keep doing me just like that. Oh yeah, oh yeah, Yes, oh yes. Oh Bret."
She snuggled into my arms. "Now, you need to fuck me. Get on top, and push in slowly. There's no rush."
She used her hand to guide my cock inside her pussy. This time I pushed all the way in. "Just hold it right there. Get comfortable with being in my pussy."
"Elaine, this is the greatest thing ever."
"I thought that blowjob was the greatest thing ever."
"Well, it was until now."
"Let's see if we can make it even better." She started to move underneath me.
"Oh yeah, Elaine. Oh, that feels good."
"Now, move with me Bret. Push in and out, in and out, that's it."
"Oh yeah, Elaine, you make my cock feel so good."
‘Faster, Bret, faster. Slam it in there. Oh yeah, oh yeah, just like that."
"Aaaah, aaaah, aaaahh," I moaned as I came.
"Bret, that was so good for your first time. It'll get better the more you fuck, and I expect you to fuck me a lot."
A half hour later I was on my way home, and I was high. Nothing could change my mood. Friday, work flew by, and Happy Hour was a lot of laughs. Elaine was there, "I have plans for the weekend, but next week after Happy Hour why don't you plan on spending the night?"
There was nothing like that weekend; all Elaine wanted to do was teach me how to fuck. "Get behind me, Bret. Just like that; fuck me like a dog."
Or she'd get on top, with those beautiful tits bouncing almost in my face.
Don't' get me wrong there was lots of sucking, too. That's how Elaine revived my cock.
By Sunday afternoon, that 40-something woman had worn 22 year old me out. I went home after a late breakfast, and slept until it was time to go to work Monday morning.
We saw each other the following weekend, and as I left, Elaine said, "Bret, next weekend is a three day holiday weekend. I have a little cabin on a lake about two hours up north. Why don't you come with me? I promise you'll have a great time.
Of course, I'd go and that long weekend changed my life.
Her little cabin turned out to be a three bedroom A-frame with an enclosed porch and a beautiful view of the lake. "I have three acres, and it's very secluded. I even go skinny dipping once in a while, but right now, I want to take you to bed.
As soon as we were in bed, "Bret, when we first met, you were a virgin, and had never had a blowjob, right?"
"Right. All of that's in the past now. I can't fuck you enough, and the way you suck my cock . . ."
"Here's another question for you, have you ever eaten pussy?"
"Ummmm . . ." Even as well as we now knew each other, I was embarrassed to say that I hadn't.
"I'll take that as a no. This weekend you're going to learn. Don't worry, you'll get to fuck me, and I wouldn't go without sucking your cock. Come on, get between my legs."
By this time, I'd seen Elaine's pussy before when we were fucking, but now I had a close up view. Looking back, and comparing her to lovers I've had since then, she had a neatly little triangle of dark brown hair; not much different than the hair on her head. Her major labia were bare, and they were starting to open. It already looked wet in anticipation.
For the next hour, Elaine showed me how to eat it, but didn't lead me to her clitoris. "Just get comfortable, Bret. It doesn't bite."
It only took me a few minutes to know that I loved eating her pussy. I loved her taste, her fragrance, and just having my face in that bush. Don't get me wrong, I loved fucking her and her blowjobs, but eating her pussy was beyond amazing.
"You're getting the hang of it. Now, remember how you used your fingers on my clitoris and what that does to me?"
"Of course," I mumbled with my face still in her bush.
"Instead of your fingers, use your tongue." She used her fingers to open her pussy wider. "It's right there for you."
As much as I loved her taste and her fragrance, once I started on her clitoris, the things that did to her; the noises she made and the way she moved was beyond anything that I thought possible.
It was a good thing her cabin was secluded. ‘Oh God, Bret, oh my, oh yeah, oooooooh, oooooh, oooh, you make my pussy feel so good." She was so loud.
When we were fucking, Elaine was bouncing that ass off the bed; her hips were moving and her legs were pumping like she was riding a bicycle. Now, she was even more animated, and after her orgasm, she'd wrap those legs around my head, and gently fuck my face.
Once the initial stages of her orgasm passed, she'd spread those legs, "do my clitoris again, Bret, do me again. You're so good to me."
By late Friday night, Elaine had by my count had at least four orgasms, and "Bret, you're such a fast learner, You want to be my pussy eater, don't you?"
I could only nod yes. My face was still in her bush. I crawled up and slept with my head cradled in those lovely tits.
In the morning, Elaine was full of energy. "After what you did to me last night, there's nothing I'd like better than to start our day with a blowjob."
Since that very first blowjob, Elaine had been an energetic cocksucker. This morning, "Bret, my pussy is still tingling from what you did to me last night."
Then she sucked my cock like never before. After all the time we'd spent together, she taught me how NOT to cum until she was ready for it: whether it was in her pussy or her mouth.
She spent much of the morning, sucking, licking, teasing, and when I came, "hmmmmmm, hmmmmmm, hmmmm, you taste so good this morning."
After a walk along the shore, there was fucking. "Bret, after what you did to my pussy last night, it needs your cock badly."
Late in the afternoon, "Bret," she said as she poured a glass of wine," I'd like to sit naked on the porch, while you're on your knees learning to eat my pussy. You should get undressed, too. How does that sound?"
Elaine watched the sunset, sipped her wine, while I ate and ate. She was directing my tongue. It might have been the best Happy Hour ever.
In the morning, "Bret, what would you like to do today?"
I think I surprised her. ‘You could sit on the porch drinking your coffee while I eat your sweet pussy."
"Oh Bret, what a wonderful idea. You're such a good boy. It'll take a while for the coffee to be ready, I'll take a shower."
By the end of the weekend, "Bret, you've become an excellent pussy eater. I'm going to want your tongue all the time when we get home. Not that I don't want to fuck you and blow you, but the way you eat me has me climbing the walls."
"Elaine, there's nothing I like better than eating your sweet pussy."
"It's yours anytime you want it. Oh, and Bret, after you eat me, and we fuck or I blow you, I don't think your cock could get any harder. I love seeing stand up. My God, you're like a flag pole."
I'd noticed that, too. Sometimes when I was eating her, I thought for sure I was going to cum.
For the next month, Elaine and I saw each other just about every weekend. We fucked, she sucked, and I insisted on spending a lot of time eating that 40-something pussy.
TO BE CONTINUED
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