In a Class of His Own Ch. 08

It was a weeknight, unfortunately, so we couldn't stay out too late. When I drove her home, I had hopes that she might invite me in.

- "Thank you." she said, softly. "That was a wonderful evening." She kissed me, and leaned in for more. She slipped her dainty tongue between my lips. The kiss grew a little more passionate.

I reached over, and cupped her breast - Anna was a B cup, at most, but I wasn't addicted to size. It was Anna's breast, even through her bra, and that was exciting enough. She gasped into my mouth as I stroked her, softly.

When I moved that hand to her thigh, though, she pulled back.

- "Not tonight." she said. "But ... you've been so patient, Chris. You've never complained about how little time I have for you. And how ... we don't get much time alone. You deserve a reward."

Anna kissed me again, and then she put her hand on my thigh. She kissed me harder, and then reached for the buckle on my belt. Somehow, without breaking the kiss, she got my pants undone, and the zipper down.

She reached into my pants with her delicate little hand, and pulled out my rapidly growing erection. Only then did she break our kiss, to look down at what she held.

Now, I'm not hung like a horse, but compared to her tiny hand, my dick looked enormous. Anna took a good, long look.

Then she returned to kissing me, while she stroked my cock.

I had been hoping for a lot more, but I wasn't about to decline a handjob from a beautiful girl. Is there such a thing as a bad handjob? Besides, it had been a while since my dick had spent any time with anybody else's hand except my own.

It didn't take long before ... "I think I'm going to -"

I came hard. The first spurt shot straight up in the air, and nearly hit me in the face. Anna tilted my cock, pointing it away from her - I guess she didn't want to stain her dress. My second shot splashed across the steering wheel and the side of my door. I got my hand over the top of my dick, to catch most of the rest - which made quite a mess over the top of my pants.

- "Oops!" said Anna.

She fished in her purse, and found a small packet of tissues. She offered them to me, almost apologetically. "Sorry." she said.

***

In terms of sexual activity, that Valentine's Day couldn't match the previous one, with Chantal. But it was a big step forward with Anna. And I had every hope that she would prove worth the wait.

I saw her at school, and we had opportunities to chat. We also met with our environmental group. But fifteen hyper pre-teens tend to monopolize your attention.

There was no way that I blamed Anna. I was still working my butt off - weeknights were too busy for me, too. But I was hoping to juggle school and a social life. She was trying to manage those - and her family.

- "I can't, Chris." she said, after I suggested a quiet night at my place. "It's my Nonna's birthday. Family stuff. I'm sorry."

- "That's okay. I understand." I did understand. But it didn't help me with my simple problem: I was itching to get into Anna's pants.

- "Unless ... do you want to come?"

- "To your grandmother's birthday?"

- "It would be a chance to meet my family." she said. Her head was tilted slightly downwards, and she was looking up at me, under her eyelashes. She had a shy smile on her face - I realized that this was a test, or at least an important landmark in our relationship.

- "I would love to meet your family."

Anna smiled. That was the correct answer.

I've seen some big families, but Anna's relatives could be counted by the dozen. I met her 4 brothers, two wives, and four kids. I met Cousin Sal, Cousin Gino, and other Cousin Gino. I was introduced to Uncle Rocco, Uncle Joe (Giuseppe), and Uncle Sal. I met cousins Maria, Angela, and Theresa. And that's only the ones I remember.

Anna's parents were short, and shaped like Brussels sprouts with heads. It blew my mind: how could these two homely little people have produced a beauty like Anna? Then I was presented to the matriarch, Nonna Maria herself. I had brought flowers - they were scanned, and accepted.

Mother Colaiocovo made sure that I was fed - continually. In my house, we were taught to clean our plates, because there were starving children somewhere. But every time I did that, Anna's mother appeared to put more food on it. I felt like I was going to burst.

- "Just leave a little bit." said Anna. "If you finish everything, it means you're still hungry."

Her mother approved of my appetite. Nonna wasn't so sure.

- "He doesn't look Italian."

Anna's unmarried brothers took me under their wing. That is, they made sure I always had a beer, talked sports with me, and then started asking me to taste shot glasses of grappa. I wasn't born yesterday, though, so I went easy on the stuff.

Nonna had had plenty of birthdays, but I was a novelty. Everyone had a question or two for me: what did I do, how had I met Anna, where did I go to church ... Anna helped me out when she could, but she was one of Nonna's chief ladies-in-waiting, and was kept hopping the whole time.

I stayed for a couple of hours. Anna had let me know that we could arrive together, but that she would have to stay and take care of her grandmother. When I was ready to leave, Anna escorted to me the door.

- "You were wonderful. Everybody was talking about how nice you are." she said.

- "They were all very nice to me - even though I'm not Italian."

- "Don't worry." she said. "I'm not that traditional." Then she leaned in and kissed me. "I really appreciate that you came tonight."

- "It was my pleasure." I said.

- "Well ... to show my appreciation, I'd like to make you a home-cooked Italian meal. At my place. Would next Saturday be OK?"

There was a world of promise in her eyes, and in that beautiful smile.

- "That sounds ... great." I said.

That next week at school was interminable. I was jumpy, and short-tempered. Antonia noticed it, and called me on it.

- "Lighten up, Genghis." she snapped.

I jerked off every night that week, and twice on Friday, trying to keep the tension from getting to me. My imagination was running wild.

I showed up at her door with flowers and a bottle of wine. She was wearing a dress, and a big apron that said 'Kiss me - I'm Italian' - so I did.

The meal was actually pretty good. Anna accepted my fulsome compliments, but swore that her mother was the true genius.

- "You'll see." she said. "That is, if you want to come over for Easter. My Mom suggested it - she really liked you."

- "I'm more interested in her daughter." I said.

- "That's good." she said. "I'd hate to lose you to my mom."

I insisted on helping her clean up. She laughed and patted my ass while I washed the dishes. She dried and put them away.

Finally, we sat down on her couch, and finished the wine.

- "Thank you for coming to Nonna's birthday." she said. "You were a big hit."

- "You already thanked me." I said.

- "I said it. Now I want to show it."

Anna flowed into my arms, and kissed me. I enjoyed that for a while, and then reached for her breast. She let me fondle her for a few moments, but then she took my hand, and gently pushed it away.

"This isn't about me." she said. "It's about you. I want to thank you for waiting for me."

She stood up, and went to her tape player. She pressed 'play'. It was something by the Bee Gees, from their 'Saturday Night Fever' era.

Then Anna performed a striptease for me. Honestly - she did.

She was a reasonably good dancer. But I was watching her face - most of the time. She unzipped the dress, slowly ...

It was a very sexy strip. In retrospect, though, I would have to admit that Anna's body wasn't the most exceptional I had ever seen. She had thick legs. Her ass was nothing to write home about. I already knew that her breasts weren't large - but her nipples were erect, and that was a plus. It didn't matter, though. If you could have seen her face ...

She didn't take off her panties. I didn't know if that was because of her cycle, or out of shyness. Anna knelt in front of the couch, and her fingers went to my pants.

- "Let's get these off." she said.

Anna gazed her fill at my erection this time. She studied it, considered it from several angles, and stroked it, from root to tip. Then she looked into my eyes, with a big smile ... and she dipped her head ...

She licked the head of my cock, ran her tongue across it. Her hand went lower, to cup my balls. Then Anna took me in her mouth. She licked, and sucked, and stroked the base of my cock with one hand, while caressing my balls with the other.

Months of anticipation probably contributed, but I found the whole experience incredibly exciting. The sight of her beautiful face, wrapped around my pole, was more than I could handle. I warned her that I was about to come.

Anna gave me another lick, then pointed my cock at my navel. She continued to stroke me, and to rub my balls. I came all over my own stomach.

She went and got me a fistful of tissues. Within ten minutes, I was wiped off, fully dressed, and at her door. Anna kissed me, and said "Goodnight, my man."

***

I was confused.

On the one hand, I had gotten a handjob and a blowjob in the last month. And a striptease show. We seemed to be on some sort of escalating sexual progression. Anna was keen on rewarding me for good behaviour. She was stunningly beautiful. And she wasn't shy.

But it didn't escape my notice that we had been dating for six months, and we hadn't had sex. You can argue that I was spoiled, after Chantal - or some of my other experiences. I wasn't too keen, either, on this sex-as-reward thing. It reminded me of Carol.

I liked Anna, as a person. I enjoyed her company. But the sex was an issue. She had thanked me, twice, for my patience. That seemed to suggest that there would be a payoff, at some point. Could I wait? Should I wait?

I got a letter from Sarah - Steve's sister. She was still in university, and had a boring class. To pass the time, she was writing me a letter. She had dumped Jason, and was considering her future.

In my reply, I congratulated her for moving on from a guy who didn't respect her. I told her about my school, and then - I don't know why - poured out my concerns about Anna. When I was with Moe, or Nina, or Chantal, I had no doubts. Why was I so conflicted about Anna?

Then, to my surprise, I got a phone call.

- "Hey, Chris!"

- "Nina?"

- "Yep - it's me."

- "What's the occasion?"

- "No occasion. Just wanted to hear your voice." she said. "OK - I do have a question."

- "Shoot."

- "Can I come visit you? I want to get your opinion - your advice." she said.

- "Of course you can." I said. "When?"

- "Labor day?" she said. "Just for the long weekend."

- "Umm ..." I felt incredibly self-conscious. "You know I have a girlfriend."

- "Yeah - Anna." she said. "I won't mess that up on you, Chris. Purely platonic visit."

- "Sounds great." I said.

***

At this stage, I was trying to be as patient as possible with Anna. She was worth the wait. Besides, her rookie year was almost over. Next year - and each year thereafter - she would have more free time. So I hoped, anyway. I had some ideas about how she could use that free time.

Then it struck me - I was thinking a year or more in advance. Was I considering a commitment to Anna? Surely I couldn't plan a future with her, if we hadn't ever slept together - but was I that shallow, to hinge everything on sex?

One Saturday date, at the beginning of June, consisted of taking Nonna shopping. I would rather have dental surgery than go through an ordeal like that ever again. For Anna's sake, I swallowed my pride, and suppressed the urge to run from the store, screaming.

By the time we got the old lady home, and unpacked everything she had bought, I figured that I deserved a medal, or some kind of award. Anna kissed me on the cheek.

- "Thank you, Chris." she said. "That was sweet of you."

The next Monday, at school, she came to see me at the end of the day. Anna didn't approve of PDAs in front of the students - and you never who was around - so she didn't kiss or hug me at work.

Today, though, she sat on the corner of my desk, and smiled at me.

- "There's my man." she said. "You were such a trooper, on Saturday."

- "It was nothing." I said. Well, nothing that I'd ever want to repeat - but I didn't say that.

- "You were wonderful." said Anna. "Nonna wants to thank you - she's making you her lasagna." Oh, no, I thought. Dinner at Nonna's? God help me. "I thought that I could pick it up next Saturday afternoon," continued Anna, "and then you could come over for dinner at my place."

"You deserve a reward." she said, with a smile. "And I have a special treat in mind for you." She took my hand, and squeezed it.

Now that sounded much better.

"I have to run." she said. "Lots to do this week if I'm going to be spending Saturday night with my man."

I tried to keep my expectations low, that Saturday. Maybe 'special treat' meant another striptease and blowjob. But I was dying to get my fingers, my tongue, and my cock inside her. I couldn't help it: I kept hearing Rod Stewart again, singing 'Tonight's the Night'.

Nonna's lasagna was pretty good. I was distracted, though. Anna was wearing a pink top that left her midriff bare. I was trying to catch a glimpse of bra or underwear, hoping for a clue: was I in line for another blowjob tonight, or did she have more in mind?

Anna wouldn't let me help with the dishes this time. She took me by the hand, and led me to the couch - and past it, into her bedroom. My blood started to flow south.

It was a girly-girl bedroom, pink and frilly. There were stuffed animals and about eleven extra pillows on the bed. None of that mattered: my eyes were on Anna. She performed another striptease for me, slowly removing her pink top, to reveal a little pink bra. The panties she wore were pink, too.

She could have been wearing a garbage bag, at this point. I wouldn't have cared. I drew her to me, and kissed her. I fondled her little boobies, and then lowered my head to lick and suckle at them.

I wasn't going to last long, once I finally penetrated her. So I wanted to give her at least one orgasm first. I picked her up, and reverently placed her on the bed. Then I spread her legs, and dipped my head between her thighs.

- "No." she said. "You don't have to - " She actually tried to push my head away.

I took hold of her little hands. Then I looked her in the eye. "I want to, Anna."

If you've read my story this far, you know that I've spent a fair bit of time eating pussy. I don't claim to be an Olympic medalist - but I do know my way around. So when I say that Anna was a challenge, you might understand what I mean.

She was stiff. Tense, and unresponsive. It became abundantly clear, after a few minutes, that Anna wasn't particularly enjoying this. I was a bit shocked. She was the first woman I had ever met who didn't like having her pussy licked.

That was a challenge to my semi-pro skills, so I did my best to relax her, and simultaneously to arouse her. It felt like she was fighting me, actively resisting. Well, fuck that. I got aggressive, and grabbed both of her ass cheeks, pulling her hot little cooch into my face.

I won. Less than a minute later, Anna sighed - it was like the air going out of a balloon - and her whole body seemed to relax.

That was good enough for me. I stood, and shucked my pants. I rummaged in my pocket for a condom.

- "You don't need one of those things." she said. "I'm on the pill."

She lay back on her bed, as I slid between her legs.

"I love you, Chris." she said.

I hesitated, for a moment. This was the first time she had said those powerful words. Why right now, when I was completely in the grip of overpowering lust? It nearly threw me off. I hadn't waited nearly nine months to stop now ...

And then it hit me.

Oh my God - I'm dating Carol again. Anna had kept me waiting for months, before surrendering her ultimate prize. My cock wilted.

- "I ... I can't." Shit! Was this the equivalent of leaving her at the altar? I had absolutely no desire to fuck Anna, at this moment.

- "Are you alright? Chris - what's wrong?" she said.

- "I ... I don't feel good." Lame. But I couldn't think of anything else. "I don't know. Performance anxiety, maybe. I just ..."

- "Oh, my poor baby." she said.

Anna would have cuddled and coddled me. But I needed to get out of there. I apologized, profusely, while I got dressed.

"It's okay, Chris. These things happen." she said.

Only to me, I thought. Twice is two times too many. Anna accepted my lame apologies, and let me leave. I think she was as embarrassed as I was.

Once I got home, I cracked a beer, and sat down next to my window, looking out into the semi-darkness.

What the fuck was I doing?

The tears rolled freely down my cheeks. After all this time, after all of Moe's lessons, I was still a complete fucking idiot.

How had I not seen it? Anna wasn't for me. I had asked her, once, where she saw herself in five, or ten years. She was addicted to her family, and perfectly content to raise children of her own in the town where she had grown up. She had never even contemplated living elsewhere. Travel didn't interest her at all.

How could I have been so blind?

For some reason, it was at that particular moment that I remembered what Sarah had asked me: Do you love her?

Anna was Carol, all over again. She wasn't a bitch, but there were striking similarities. Sex was a reward, 'a special treat', once I had earned enough points, or done something to deserve it.

She didn't enjoy sex. It was something that men wanted, and so a commodity to be traded, in return for ... taking Nonna shopping. Anna had called a condom 'one of those things'. I wasn't even sure what that meant. Was a pretty face worth all of his bullshit?

I was quite certain that I would never have a fulfilling sex life with Anna. And yes - that mattered to me. I was the one who had told Sarah not to settle.

Could I take my own advice?

***