You're So Damned Cute

Brooke told me that she knows she is not what men think of as a beautiful girl. I wasn't going to lie to her and tell her she was wrong. "You know what, Brooke, you're so damned cute, you don't need to be beautiful. I'm glad you're not some centerfold Barbie."

She smiled at me. "You mean it? You think I'm cute?"

"Enough that it pains me that I'm not forty years younger, but I suppose if I were, you'd be out of my league."

This conversation followed Brooke telling me about dumping the boyfriend she'd had through high school and into college when she discovered he'd been cheating on her the whole time. At twenty-three she was damaged goods, gun shy of men and struggling with self-esteem.

I met her at a writing workshop. I noticed her immediately. She really was cute, long, dark curly hair, smallish face with nice regular features, clear olive skin, full lips, straight white teeth and a button of nose. On further examination, her body was cute too. Full rounded hips, slender neck, good posture and she knew how to fill a sweater. Some might think she was a little on the heavy side but short of what I'd call plump. I'd say healthy looking.

I was not teaching the workshop. It was being run by a local arts council and we were participants, she, the youngest, I the oldest. We met monthly and about 4 months in, Brooke and I found ourselves working together on an assigned collaboration, something I was not looking forward to. I prefer to work alone. Brooke and I both seemed to be loners. Six other participants had paired off, leaving Brooke and me with with each other by default.

The project involved producing two short stories, one by each writer, based on a story line provided by the partner. The story had to be fiction, but could be based on something true. The story line Brooke gave me when we met outside of class at a coffee shop, was the story of her break-up with the only young man she had ever gone with. I thought it was a poor choice of topic, but writing a story from the point of view of a naive young woman was sure to represent a challenge and, while it wasn't my intention to delve into private details like sex with someone so young, she had to give me enough detail about the relationship for me to hang my story on. As I interviewed her, I decided I really needed to write two stories, one that would be shared with workshop and one that was strictly for my own -- call it entertainment.

Brooke and Matt (fictional names for the story) had been together since the tenth grade. Before Matt, Brooke had only kissed one other boy. After their senior prom, Brooke gave up her virginity to Matt. It was clumsily done but the two of them embarked on a summer of love, most often in the back of Matt's car, until they went off to different colleges in the fall, pledging to be true to each other. The two of them were several hundred miles apart and planned to see each other at Thanksgiving and Christmas then on spring break and the following summer. They did this for two years, with regular lengthy phone calls late into the night in between. The second summer, Matt seemed different. He didn't seem as anxious to see Brooke. He sometimes made excuses for not seeing her that didn't ring true. Finally, a cousin, who was a senior at the college Matt attended, told Brooke that she knew why. Matt had girlfriend at school. She had seen them together on and off campus several times. Brooke was crushed by the news and even more so when Matt, apparently manning up, didn't deny it. Once the two of them broke it off, Brooke heard from other sources that all through high school Matt had been sleeping with other girls who attended schools in nearby towns, at least three of them. Brooke was beyond crushed. She was devastated and humiliated. She was apparently the last to know.

Over the four years since, Brooke had yet to date another boy, unable to trust anyone. She also dropped out of school, took waiting jobs in local restaurants and lived with her parents. To stave off loneliness, Brooke reconnected with two high school girlfriends who had enrolled in the local community college instead of going off to college. The three of them were nearly inseparable for awhile but each of her friends had gotten into relationships recently, leaving Brooke feeling left out. That's why she got involved in the writing workshop, to absorb some of her time and to connect with other people. She was a smart girl. She seemed to know what was good for her.

I was sympathetic with Brooke in a fatherly way. I suggested if she wanted, that we could meet for coffee once in awhile, even after the workshop was over. She seemed pleased to have made another friend, even one older than her own parents.

At one of our meet ups, Brooke seemed particularly sad. She told me her 24th birthday was coming and, aside from the family tradition of cake and ice cream, no celebration was planned. Her friends were all busy. I patted the back of her hand, then left my hand resting on her wrist and looked into her eyes. "What if I took you out for a nice dinner, if not on your birthday, the day after. Would that be too weird?"

Her mood brightened slightly. She said, "no, it wouldn't be weird. It would be great. It doesn't have to be a fancy place, though. I'm not used to that."

"Oh, it'll be a fancy place alright. Nothing's too good for you. You might even want to buy a new dress. If it makes you uncomfortable to be out with someone so old, you can call me grandpa while we're out together."

We settled on the details of date and time. Brooke said we could meet at our coffee shop, I'm sure to spare us both the embarrassment of her being picked up by a fake grandpa. I told her to be dressed to the nines, that I would be in a suit and tie.

When Brooke showed up for our date, I was knocked out by her look. She went with the proverbial little black dress with matching heels, light make up, gold bangles on one wrist and a simple gold chain on the other, matching one that she wore on one ankle. A triple strand of what I assumed to be faux pearls contrasted with the dress, setting off her elegant neck. The hem of the dress was high, the neckline, low. The longest strand of the pearls dipped provocatively into her ample cleavage. She was completely sexy without being trashy. I wasn't sure I'd be able to stand and walk out the place to go to the expensive dinner I had planned without my own embarrassment. I complemented Brooke profusely, causing her to blush sweetly.

The date took place in the most expensive restaurant I could find, a place known for the freshest seafood and the best wine list in the area. I was prepared for dinner for two with champagne to set me back three-hundred dollars or more. Once seated, I ordered a full bottle of champagne, not the most expensive but close to it. We had two flutes each before dinner arrived, lobster at market price.

Brooke's blue eyes sparkled in the candle light. This dinner made her very happy. She chatted away in a low voice. Twice while we talked, she reached across the small table and put her hand in mine. I was a little uncomfortable with it at first. It seemed different to me that the quick hello and goodbye hugs we shared coming and going from our coffee shop rendezvous. I attributed her flirty behavior to the champagne.

By the end of the dinner, the champagne bottle was empty through no fault of my own. I made sure to slow down because I had to drive the thirty miles back to the parking lot where Brooke had left her car, though I wasn't sure in her condition, that I would let her drive. I'd have to see when we got there.

In the car, Brooke continued to be chatty. She asked me if I liked her dress, if I liked the jewelry she chose or if it was too much. Did she look classy?. Did I notice she was wearing stockings. "They're real," she said, "you know, with lacy garters."

"Brooke -- Little Wren (I occasionally called her that, like a grandfather might do), that's the last thing I needed to know. Now I think you might be deliberately torturing me. Do you mean to be cruel? Of course I like the dress, the jewelry is perfect. So are shoes, but the garter and stockings, I really didn't need to know about that."

"I'm sorry," she said. "I didn't know I was being cruel. I just wanted you to like the way I look. You once told be I was so damned cute. I wanted to show you how cute I can be."

"Well you've crossed the line between cute and sexy," I said, "in fact you're way beyond the line. Look at you. Damn you're hot, even to a man my age, maybe more so to a man my age. I don't often resent being old, but tonight -- is different.

"Don't say you're old. You're not old. Did you notice I didn't call you grandpa once? I was at a fancy dinner with my boyfriend or -or my lover as far as that stuffy waiter knew. Did you notice how he envied you?"

"He did not, Brooke, if anything he thought maybe you had a sugar daddy."

"Well then he envied you being my sugar daddy." Brooke crossed her arms in a "so there" pose. I laughed at her pout.

"You're even prettier when you're pouting, you know. You're just making me feel worse."

"You want to feel worse? Look at these." Brooke reached into the top of her little black dress, pulling it away from her body with the other hand. She popped each of her breasts out of her bra and dress. "I'll bet you've wanted to see these for a long time. Sometimes at the coffee shop I've noticed you noticing them. I was almost offended at one time, but then I realized you never made it obvious or said anything sexual to me in all the time I've known you. I can't say that about any other boy or man I've known. Well tonight that's going to pay off because these and any other parts of me that want are yours for the asking."

At that moment, we were pulling into the parking lot next to Brooke's car. "Brooke, you're drunk," I said. "Please put your tits back into your dress. They're beautiful, in fact perfect, but please put them away."

"Yes, I am drunk, too drunk to get in my own car and drive home. No one's expecting me to come home anyway. They think I'm staying with my friends who were taking me out for my birthday. I guess that's true. I just didn't tell them what friends. So if I can't drive, you should take me home with you or, better yet, to the motel on the other side of this parking lot. I may be too drunk to drive but I'm not too drunk to know what I want. I'm not asking for a relationship. I'm lonely and horny, it's my birthday and I don't want to fuck a stranger. I want to fuck someone who cares for me."

"Brooke, you can't possibly find me attractive. I wasn't even attractive when I was your age. If I were forty years younger, you'd definitely be out of my league."

"You're not attractive," she answered, "but you're so damned cute, you don't need to be." Brooke pulled at the hem of dress, exposing the lace tops of the stockings and garters. "There," she said, "you don't have to imagine anything. I bought these for you."

I shut off the engine. "I may not be any good, Brooke. I'll do my best, but a man my age can't make any promises. I may come as quite a disappointment."

Brooke took me by the hand. She placed it flatly on one bare breast. It was warm, soft and creamy smooth. It stood young and proud on her chest. The nipple hardened under my palm. "There's no way you can disappoint me." She leaned over and put her lips to mine, slipping her tongue between them. "Take me inside, Paul. Please. It's my birthday."

I went into the motel and came back out with a room key. The motel was old, built in the fifties and never redone except to upgrade the fire safely equipment. It felt sleazy in it's way, but in a good way. I was feeling a bit sleazy myself.

Once in the room, I sat Brooke on the queen sized bed. We kissed. Brooke started to reach for the zipper on the back of her dress. "Wait for a bit, Little Wren. I want to look at you some more. Why don't you lift the hem again and show me the stockings like you did in the car." She did as I asked. I stood and reached into the bathroom and switched on the light, closing the door most of the way. Then I turned of the light in the room, making the lighting dim, but not too dim. I returned to the bed and kissed Brooke again lightly. I kissed her mouth then her neck and shoulders. I took and earlobe into my mouth and gently nibbled it. All the old techniques, not used in several years came back to me. Brooke's only lover, from her description, seemed rather ham-handed and clumsy. I wanted to give her a different experience. We kissed some more and reached behind her and pulled at the zipper on the little black dress. I kept my arms around her and stoked her from the small of her back to the shoulders, up and down, up and down until I drew a sigh from her.

I pulled the dress off of Brooke's shoulders, as I returned to kissing her pretty neck. She started to get up to remove the dress, but I told her no. I wanted to see it bunched around her waist. I though it would be sexy that way, at least for awhile. Her breasts stood out in a tiny lace half bra that barely covered her nipples, which were large and puffy, the sort of nipples I had dreamed of at times but never got to see except in pictures in adult magazines. I bent down and kissed one them several times before taking it between my my lips. I heard Brooke moan. I sucked the nipple and flicked it with my tongue at the same time. This brought a louder moan followed by a deep sigh. Brooke's nipples were sensitive. That pleased me greatly.

I lifted my head to kiss Brooke again. This time more firmly. More aggressively. "You know, you're only the third man to ever kiss me," she said, "and by far the best."

"Where have you never been kissed, Brooke. Where shall I go next." I slid my hand under the hem of her dress, caressing my way up to her panties. I gently touched a finger to the crotch of the thin garment. "Has anyone kissed you here? You know, I'm about to."

"Please," she said, "I want you to be the first, the first man ever to kiss me there."

I laid the young woman back on the bed and slid my hand back between her legs, caressing and tickling her stockinged thighs as I moved the dress up out of my way, gathering it at her waist. The thin lace panties matched the bra. I rubbed the satiny smoothness into her cleft, feeling the moistness start to soak through the cloth. There were repeated sighs from Brooke. "That feels so good," she said. "I like the way you're touching me and taking your time."

I turned Brooke so that her legs were off the bed, resting on my shoulders. I kissed and licked her thighs above the stockings and garters, pressed my lips and mouth against her panties and her pussy lips through the sheer fabric. I rubbed my chin up and down her slit kissing the panties and rubbing my nose over her clit. Brooke was moaning somewhat louder now with every exhale. I knew she had to be close. I backed off and returned to licking and kissing her thighs. "Why'd you stop?" she said. "Please don't stop. It felt so good, what you were doing."

"You have to be patient, Little Wren. We have all night. I'm going to make sure you understand what it means to be treated the way you deserve." I took her legs and turned her back onto the bed. I removed her shoes and caressed her feet and lower legs. The stockings made them feel like silk. I hooked my fingers into the crotch of the lace panties. I had Brooke raise her ass off the bed so I could slide them off over her feet. Brooke has a tangle of thick pubic hair over her pussy. I ran my hand through it, stroking it, petting it. I stood and removed my tie and shirt. I unbuckled my pants and dropped them to the floor, stepping out of them. I returned to Brooke, sat beside her and kissed, tongue sliding into her mouth seeking tongue. I ran a hand over her breasts letting each finger brush across the nipples.

Brooke was passively waiting to see what I would do next. I got onto the bed, head between legs. Her naked cunt was finally open to me. I touched my lips to her young pussy. "Brooke, you smell so good. I'm going to make a feast of you." My tongue roamed up and down the length of her slit, tracing it's way along the outer lips. I slipped my tongue into the entrance, moving it in and out, listening as Brooke's breathing turned to a pant. I put her legs over my shoulders so I could reach her heaving breasts and finger the nipples as I ate away at the pussy more urgently. The taste was heavenly. Brooke was moaning loudly now and she was beginning to move her hips, pushing them up to press herself into my mouth. She suddenly cried out a loud "YES!" and grabbed for my head pulling me against her more tightly. The orgasm continued for what seemed a long time. Brooke held my mouth to her pussy until it was finally over. When it was done, she was trembling.

"Is that what an orgasm is supposed to feel like? I had no idea what I was missing."

I untangled myself from Brooke's, legs so that I could get to the edge of the bed to remove my boxers. "Are you disappointed Brooke? It's not very large. Just average, I'd say. I'm going to lay down beside you and I want you to play with it. Don't try to make me cum. Just squeeze and stroke it to make it hard. It'll take longer with an older man. It's even better if you nuzzle it and rub it on you face and tits. Give it little kisses. Have you ever sucked a cock, Brooke. I'd love to have you suck my cock."

"I have," she said, "but Matt told me I didn't do it right. He made me stop after a few minutes and I never did it again."

"There's no wrong way to do it, Brooke. Take your time and pretend it's an ice cream cone. Use your lips and tongue on the end. Take it in your mouth if you want to, but only if you really want to."

Brooke put her hand around my cock and planted several small kisses on the tip. She licked around it, then went up and down the length with her tongue, as it grew to full hardness. I let her know how much I liked it. She looked up at me and smiled. She changed position and dragged one tit across cock and balls. "Yes," I said. "You're getting me so hard. You're so sexy looking. Kiss and lick my balls too. Yeah, just like that, baby. You are wonderful."

I rolled Brooke over onto her back and straddled the trunk of her body. I lay my dick between her tits and pushed them together around me so that I could saw my cock between them while I stimulated her nipples with my thumbs. She told me how hot it looked to have me fucking her tits. I told her to lick the head of my cock when I pushed through the tunnel. After awhile I let the breasts go and put an extra pillow behind her head, scooting forward to push my cock to her lips. "I want to fuck your sweet mouth now, Brooke. Open your mouth for me and cover your teeth with your lips. Wrap your hand around me so I can thrust in and out without hurting you. There you go, baby. Just like that. Oh, you're a good little cocksucker. Hmmm, that feels to good." I kept the pace slow and fucked Brooke's mouth. I loved the squishing sounds her mouth produced. "Look at my eyes while we do this, baby. It's so sexy to watch your eyes while I do this."

I stopped trusting and drew my cock out of her mouth. I had her lick my balls some more then scooted back down her body to spend more time on her tits and nipples. Before long I had to get into that sweet pussy. I put my cock at the entrance and rubbed up and down the length of her before putting just the head inside her. "Are you ready, Little Wren? Do you want my cock in you now? You have to tell me."

"Yes, please. I want you inside me."

I pushed forward into Brooke's moist tunnel. She was tight but so wet, I met little resistance. Once buried in her I laid still on top her, reveling in the feel of her body. "Baby, you feel so good I may never want to leave." I began stroking her slowly, listening to her little moans and the changes in her breathing as her excitement grew. "Can I cum inside you Brooke. Do you want me to cum in you?"