Anna

"Amazing."

"Anyway, the show was over and we had to hitchhike home, but Peggy had been talking to this guy on the way out the door, and she gets us a ride. We're in a VW bus that's more primer than paint with these two guys we didn't know. One thing leads to another, and we end up making out with these guys in the back of the van after they get us buzzed."

"That's how you met your husband?" I asked. "That sounds so cool."

"Actually, to be honest I didn't end up with the guy I made out with," Anna admitted. "My future ex-husband was the guy Peggy was with. He said that once he looked over at me and saw me... well, never mind."

"Saw you what?" I asked, while Anna covered her face with her hands and kept saying no.

"Okay," Anna said after she stopped giggling, and then she whispered her secret in my ear.

"So there!" Anna said, her face flushed after dropping that bomb on me and watching my reaction when she admitted that her future husband loved the way she was performing fellatio on his friend. "I wasn't always the little old spinster brushing her hair by herself."

"I love you," I said, and when that didn't seem to register as Anna stared at me like I had just clubbed her over the head, I repeated it, taking her face in my hands and kissed her.

Anna was obviously stunned when I started kissing her, but it wasn't resistance that made it an awkward moment. Necking was something that I hadn't had much practice at, and besides, Anna was on my right side, while in my limited experiences I had always been more comfortable with the girl on my left.

Anna finally eased herself away from me, and when I realized how aggressive I had been I braced myself for a well-deserved slap in the face. A slap that didn't come.

"Easy Tommy," Anna said, her lightly weathered and gently wrinkled face still there, and her hazel eyes full of understanding. "Easy."

Anna took my face in her hands and kissed me, a kiss that was every bit as passionate as my amateur efforts, but so much more erotic. Anna's lips were soft and warm, and when her tongue slipped into my mouth I was startled but responded in kind.

My hands went up and down her back as I hugged her, and that kiss hardly ended when the next one began. I was leaning Anna into the back of the couch, with her steadying influence keeping my animal urges in check somewhat.

Anna had taken her glasses off at some point, and as we kissed I brought my hand around to her chest. Anna did not protest but only groaned when my hand found her breast through her dress and brassiere. The flesh underneath was very soft and pliant as I groped her breast roughly. I was a bit shocked at the size of her breasts, and it was as if she was pushing herself into my hand as we necked.

It was then that I felt Anna's hand on my lap, her fingers clutching as she searched for my dick through my slacks. I was hard as a rock, but it still took her a while to find my boner, which says a lot about the size of it.

"Ohh," Anna cooed in my ear when she found my dick, and then her fingers were taking down my zipped and reaching inside the fly of my pants.

"Ooh," we said in unison after her fingers slid under my underwear and took hold of my penis and pulled on it as best she could given the snug surroundings.

"You're not small, Tommy," Anna sighed into my ear, giving me a sweet lie as she lightly stroked the slender five inches I was blessed with. before reaching lower and rolling my balls in her palm. "Nice to feel a man again. It's been so long."

My hands were all over Anna, running my hands all over the petite five foot frame through her clothing. Anna was breathing heavily in my ear all the time, and when I tried to work my hand under her dress she stopped my hand.

"Tommy," Anna said, her cheeks flushed as she caught her breath. "Are you sure..."

"I want you so bad," I said, hoping that just because my words came out with an excess of emotion that she didn't think I was lying, but it was just a case of me wanting her to know how excited I was.

Anna nodded and got up off the couch, taking my hand and leading me down the hall.

"Here," Anna said as she led me into her bedroom, a small cube full of knick-knacks and crocheted things of all kinds. "I'll be right back."

I stood in the semi-darkness of her bedroom, wondering what I should do. In the end, I took my clothing off, even my socks, and after I folded them and set them aside I happened to catch a glimpse of myself in the mirror over the dresser.

"Oh brother," I muttured as my eyes began to adjust the the dim light provided by the moonlight that made it though the drawn curtains.

My skinny frame was hardly the kind that women drooled over, and as for the sad spout that stuck out in front of me like a thumb when my eyes went lower, I cringed. Why couldn't I be like those guys in those websites, with their big schlongs waving around while they stood their smugly? No wonder Jill had giggled. I was pretty pathetic.

The more I waited for Anna, the more I worried. My erection disappeared and then my dick started to attempt to crawl into my intestines as I thought about every possible thing that could go wrong. Anna? Where did she go? Did she get cold feet like my science teacher had?

Then the bedroom door opened, and Anna was in the doorway, the light from the hallway forming an aura around her briefly before she stepped inside and closed the door behind herself.

"Tommy?" Anna said, her eyes probably not as adjusted as mine were.

"I'm here Anna," I whispered as I stood a few feet in front of her.

"I'm scared," Anna said.

"You're scared?" I said with a nervous laugh. "I thought you took off on me."

"No," Anna said softly, jumping a little when my hands touched her shoulders.

Anna had let her hair down, out of that tight little bun, and as I ran my hands through her wiry black and silver locks she eased herself into my body.

Anna was wearing a bathrobe, and when I slipped my hands inside the lapels of the garment I could tell she was naked underneath. I gently parted the robe and then it was sliding to the floor behind Anna, exposing her pale and petite body.

Anna shuddered as my hands slid down her arms, and I knelt before her as I buried my face between her breasts. Her breasts were larger than I had expected, perhaps because of the way they hung down loosely. They were like baseballs hanging in stretching bags, and as my hands came underneath them and took them in my palms, Anna let out a moan that had a bit of vibrato to it.

Banana boobs - that was what my friend Zach called the tits of this girl at school that never wore a bra, and I guess Anna's breasts fit that description. The spongy orbs felt incredible in my hands though, and I could feel her nipples get stiff the more I played with them.

We somehow got over to the bed, and as Anna eased onto the bed my hand went between her legs. The hair was sparse down there, and she was very wet when I touched her sex, a sort of oily moisture.

"I haven't been - my husband - it was over 20 years ago," Anna said to me as I felt was had to be some kind of lubricant, something she must have applied to combat the dryness that comes with age.

I hadn't been born. It struck me that the last time she had sex, I hadn't been born, and probably hadn't even been thought of yet. Now, there I was.

"Easy honey," Anna whispered as I climbed between her skinny thighs, with my stiff dick in hand.

"No," I muttered as I fumbled around the lubricated opening, and the more I fumbled, the more I thought. The more I thought, the more all the these horrible scenarios came into my mind.

"Sorry," I practically cried as I tried to push what had become little more than a peanut into Anna's pussy, and I was on the verge of actually starting to cry when I realized this was going to be just like the time with Jill, only I didn't cry with her because she meant little to me. Not like Anna.

"It's okay," Anna was saying, reaching up and running her fingers down the side of my face with her right hand while her left hand went down.

"It's okay, Tommy," Anna sighed, taking my limp dick in her hand and pulling on it. "We're both nervous. It's going to be okay. See. You're getting harder already."

I didn't think I was, but Anna was so reassuring, and her touch was so sweet, that I started to believe her. This WAS going to be alright, and as my dick really did start to get hard I started to relax.

"That's it, Tommy," Anna cooed. "Yes! You're so big and hard!"

This time, Anna didn't wait to see if I would screw up, and simply took my dick into her. As I slid into the snug fold, my cock grinding into the tight membrane, Anna cried out loud. So loud, that if my hard-of-hearing Grandma was still next door she would have been calling the police by the time Anna's guttural wail subsided.

We were both laughing and crying as I moved in and out of her, the glorious feeling of being inside of a woman even better than my wildest fantasies. Anna was kissing me while squeezing my arms, and I was starting to figure things out okay myself, or at least that was how it seemed.

Suddenly, Anna's eyes bugged out wildly, and her already tight grip on my arms became almost savage, with her tiny little fingers seizing me in what seemed like a death grip. The look on her face was so foreign and so erotic that I could not look at her for fear of cumming.

As Anna arched her neck and cried out again, her body spasmed, and then my dick got crushed by a series of seizures that made me cum, her muscles almost forcing my orgasm out of me as we came together.

When I finally stopped squirting my seed deep into Anna's womb, I looked back down at my little lover, and the look on her face must have mirrored my own, because we embraced each other and held on tight for a long long time.

***

It was way past midnight when I woke up from a very light sleep, apparently having drifted off in Anna's arms for a second, and now as I looked down toward the foot of the bed, I was treated to a sight that had to be real because it was far beyond my wildest dreams.

Anna was down there, laying across my thigh as she held my erect cock straight up, while her tongue worked along the underside. When she peeked up at me from behind my dick - a dick, by the way, that didn't look so little anymore to me - she giggled and apologized to me for waking me up.

"Just in case it takes me another 20 years to lure a man into my boudoir," Anna chirped before breaking into her little giggle.

Her tongue played with the tip of my manhood, and then she let her lips slide down slowly, all the way until her nose was in my pubic hair, and then went back up.

After a couple more trips up and down, she got up to her knees and lifted her right leg gingerly over my crotch while rubbing my boner up and down the opening of her sex.

"Mmm," I said as I enjoyed the sensation, reaching up to brace Anna, holding her under her arms while her worked me into her.

Anna giggled when my thumbs stroked the sparse spray of hair nestled deep in the pockets of her moist armpits, fur which she had profusely apologized for earlier but I found as erotic as the rest of her mature little body.

"Ah!" Anna sighed as my dick went in her to the hilt, and as she started rocking on me my hands went to the banana boobs which had begun to swing wildly in front of me, morsels too tempting to ignore.

"Oh!" Anna said as she grimaced with her movements. "I'm going to regret this in the morning."

"It is morning," I reminded her.

"Then I guess I was wrong," she cackled as her thrusts become harder. "Because it still feels good!"

***

I've gone back to school since that magical summer night, but Anna is still on my mind. When I go home for winter break, I've already invited myself to Anna's house to spend a week or so.

Actually, it was Anna that suggested I would be welcome to stop some night when recess came, and when I told her that I thought maybe a week would be nicer, she seemed really excited about the prospect. So excited that she said she was going to take that week off from work, so we could enjoy each other all we could.

After I got back to school, I happened to get a date with a girl who worked at the cafe on campus. She invited me to go home with her, and late that night we went to bed.

She didn't giggle, and I didn't go limp, and she seemed to cum really well both times we had sex. We see each other from time to time, but to be honest, she's fun and pretty, but she isn't Anna.

I told Sandy - that's her name - that I had a girl back home that I was in a relationship with, and she seemed fine with that. I didn't mention that the "girl" was over 40 years older than her. Don't know how she would have taken it, let alone if she knew that a lot of times when we're making love, I'm thinking about Anna.

...

thanks for reading