Extra Virgin

I had been studying in the library for midterm exams when I felt a tap on my shoulder. I figured it was one of my guy friends who wanted some notes from me. I was wrong.

In college, I was basically a very shy guy who, although I looked like the young Al Pacino, I rarely dated. Just didn't have the guts or confidence to ask girls out, so it was with much surprise that I found that the woman who'd tapped my shoulder was someone I'd seen around and admired.

She was about five and a half feet tall with slender hips and fairly large boobs, but it wasn't her boobs that kept me interested ... it was her madonna-like face and her piercing, pale blue eyes which looked all the more striking because she had long, straight dark brown hair.

We left the library to take a break from our studies and sat on the lawn on a cool autumn afternoon. It turned out that she had been noticing me and wondered why I'd never introduced myself. I owned up to my shyness and she laughed and kissed me on my cheek.

"You're so damned cute," she said. "I figured you had a girlfriend."

"Nope. Haven't had one of those since my sophomore year."

We were both juniors at the time and I found that she wasn't dating anyone either. She was a few years older than I was. As we got to know one another, I found out that she had been married but was now a widow. Not knowing what else to say, I just told her that it sounded like she'd been through a rough patch.

She told me that she was fortunate in that she had a very close family. We both lived in the Bronx and she told me her family owned a very well-known Italian restaurant in a very Italian district. She had been working in the restaurant and going to school to fill her lonely hours. "When Jimmy, my husband died, it was like I lost a piece of me and i just didn't feel like having a social life."

Ooops, I thought to myself, there goes hope down the tubes. Damn! We talked until it started to get dark; I told her I really had to study and she said he had to go to work. We exchanged phone numbers and I promised to keep in touch.

What I hadn't told her, partly because we never discussed sex that afternoon, was that I was still a virgin. I'd gone to a boys-only school and hadn't been in a co- ed setting until I'd gotten to college. Okay, no excuses. It was partly that shyness thing again. It's not that I didn't want to, mind you, but there seemed to be no way for me to meet girls.

I called her the following night. My twenty year old heart thundered in my chest as I dialed the number she'd given me and I misdialed twice before getting it right. There was nothing to worry about, though because things felt as easy to say on the phone as they had been on the campus. She told me she would be closing the restaurant early that Sunday and that I should meet there and that she'd make me a nice Italian meal. How could I refuse?

I happen to love Italian cuisine and looked forward to it with and empty stomach and, I'll admit, a hard cock. At that point in my life, I didn't own a car and neither did any of the members of my family, so I took the subway and two buses, getting to the restaurant about fifteen minutes late. The doors were locked, but I knocked and, even though the lights were out in the dining area, I could see that the lights were still on in the kitchen. I waited a few minutes and Anna came to the door wearing tight black pants and a fairly low cut knit sweater.

Did I say I'm not a boob guy? The moment I saw her, I reassessed my values in that department. Shit... they were even freckled and freckles had always been a thing for me. I could smell wonderful smells coming from the kitchen, but whatever perfume she had on made the smell of the food inconsequential.

We ate in the kitchen and the food was out of this world. I'd honestly never tasted anything like the feast she'd prepared for us. Wedding soup, plates of antipasto, fresh baked bread, cheese plates, some kind of grilled eggplant and roasted peppers on a bed of red wine pasta, tiramisu for dessert and, of course, a nice red wine to go with the meal.

I couldn't believe how full I felt and she felt likewise. I talked about my own love for cooking and told her how excellent the food she cooked was.

"I can't boil water," she said. "My uncle Pete did all the cooking for me. As an Italian wife, I'm hopeless in that area, but I have ways of making up for it."

"Such as?" I inquired as we held hands and walked around the block under the light of street lamps and a half moon.

"Well," she asked, "Are you sure you want to go there," she replied with a giggle.

I felt fortified by my glass and a half of wine, so I nervously answered, "Sure. Why the hell not? We're both adults."

And that was how we started talking about sex. I admitted to my sorrowful state of virginity and she responded that she'd never had a virgin before ... unless extra-virgin olive oil counted, she joked.

A widow at 24, she had had a great deal of experience, but she revealed he late husband was much older than she was and a total loss in the sheets, he being of the slam bam, thank you ma'am school of human sexuality.

We compared sexual fantasies, likes and dislikes (we both liked kissing and touching, laughing in bed and exploring new things). She confessed that she was bisexual and had a female lover in California where she and her husband lived. They'd had a few threesomes but he complained it was too distracting, so

eventually it was the two women who played together. And we both, it seemed, had a thing for anal sex, though she had some experience at it, but I was still wandering in the desert in that regard.

There was a neighborhood park with swings, a slide and benches around the corner from the restaurant and we mutually decided we'd sit and enjoy the night for a few before going back to tackle cleaning up from dinner.

She nestled against my side and I put my arm around her. I don't know which of us started it, but we were suddenly in the most frantically passionate of kisses that involved teasing tongues, pressed lips, teeth, and hands. That one kiss had to have lasted more than a half hour. Finally, she pulled away and looked into my eyes and said, "If you're as hard as I am wet, then we probably should take this off the street before we get arrested."

We made it back to the restaurant in an olympic sprint, removed the plates and silverware, managing to break only our two wine-glasses.

Standing pressed to one another, we replayed our park bench make-out session and explored each others ass, caressed faces, kicked off shoes, undid zippers and buttons and pressed our burning skin together, the both of us moaning incoherently.

I caressed those lovely, freckled breast and their pink, eraser nub nipples and she caressed my now-wet and very hard cock.

I took this as my signal to reach between her legs to caress her equally wet pussy lips, which literally were dripping into my hand.. I used that liquid to ease my finger inside her tight, burning pussy as she bent her legs forcing my fingers deeper inside her.

"Damn.. Not ... bad for a beginner. Oh God! I'm going to cum.. Never so fast before. Is it okay if cum? Please, Steven, make me cum. Let me cum ."

Her face, her neck and the tops of those creamy, be speckled breasts turned scarlet and, the more turned on she got, the closer I got to cumming, so I willed myself to not cum even as she groaned and sprayed my penetrating fingers with a rush of hot liquid that sprayed even on my legs.

"I squirted. I swear I never did that before. You've got magic fingers and oh shit I'm still cumming." Followed by a more forceful spray. She sank to her knees in front of me, surprising me with the first blow job of my deprived life. Two plunges onto my hard cock and she had half of my thick cock inside her mouth. Holding my cock with her mouth, she reached for my hands, which were stroking her beautiful face and placed them on the back of her head, encouraging me to force my cock deeper into her mouth and throat. Anna gagged, her eyes tearing and mascara running, but my cock went in deeper and deeper. Just as I couldn't take anymore, she reached around my hips and, using her dripping saliva for lube, she slid a finger into my ass. That did it for me. I have no idea how many gouts of cum flew out of my cock; all I know is that her face was well coated with my cum as was some of her hair. A bit of it escaped her mouth but she captured it with her finger and slid it back into her mouth. Ahh, so this was heaven!

We rested, washed up a bit, had some more tiramisu, drank another glass of wine, held hands and, as I recall, all we both said, and at the same exact moment, was, Wow!

She went to the bathroom and I started clearing the dishes and then, when she came back, she started washing dishes and I went to pee. In the men's room, I saw, as I washed up from my post prandial piss, that I had what I could only describe as a shit-eating grin on my face.

When I got back to the kitchen, I was pleased to see that she was doing the dishes in the nude. I walked up behind her, put my arms around her waist and started to nuzzle her neck.

"Mmmm. Keep that up and we'll never get these dishes done," she playfully complained, but none the less, her lovely little ass kept pressing backward onto my hardening cock. I nuzzled some more, discovering a vulnerable spot right atop the throbbing pulse along the side of her slender neck.

She moaned and I thrusted, my cock headed right against her wet pussy. "Not there, " she moaned. In my ass. I'm a good Catholic girl, after all. We both laughed at that and I swatted her ass once, announcing I'd done it for the Pope.

"Wait, she said, "Hold that thought and I'll be right back." She was back in a few seconds, having swiped a cruet of olive oil from the table. "You've never done this before but I have and ... well... It has to be done right. Let me take the lead, okay?"

I shrugged my shoulders and told her I'd give way to the expert.

I watched as she drizzled the oil on her ass, then on my cock and then on her fingers. Bent over, her breasts on the table, she slid one, then two and finally three slender, well-manicured, extra virgin fingers into her puckered pink ass hole. I stroked my extra virgin cock as I watched her perform this ritual and noticed that, as her left hand worked her ass, the fingers of her right hand were pleasuring her wet pussy.

She reached for my now-aching cock with her left hand. "Now, slowly. You're very thick and kind of big and we don't want this to hurt, so let me set the pace." And with that, she pulled my eager cock closer and closer until it at last met its mark and she pushed in with my cock and out with her ass, groaning, "Oh, baby. It hurts so good. So good." And now the widest part at the head of my cock, was safely inside her ass. It felt like a wet, velvet glove and again, it felt so fucking good that I had to use every bit of my self-control to keep from cumming inside her right then and there. "Now, wait a bit. Let me get used to it. I think if play with my clit it'll relax me."

"Who am I to say no to that?" And I did as I was instructed. Sure enough, she began easing her hips back onto my cock until it was all inside her.

"Do you like it? What do think about my ass, baby? Is it what you ... ugh ... thought it would be."

"Like it? How do I like it? Like doesn't come anywhere close to ... it's way beyond words. Your ass is perfect."

"Ohhh, please then baby, show my ass how much you like it. Fuck my ass. Cum in my ass!"

Bent over her back, I nuzzled her neck as I'd learned and gently played with her clit. Now she was starting to drip onto my hands and moaning louder and louder. I fucked her ass harder and harder, holding her slender hips and ramming myself into her. I knew I wouldn't last long, but then, I didn't have to.

"Oh God! I'm cumming, lover. Rub my clit and fuck me hard. Cum with me! Please! I need it. Cum with me!." And that's just what I did. I squirted my cum deep into her ass just as she once again squirted from her pussy.

And that was my first date with Anna. I took a cab home but I was dancing on a cloud. I finally was not a virgin any more ... not technically; I still had not had my cock inside a woman's pussy, but, I figured, pope or no pope, this too would pass. I had a girl and damn! What a girl.

Now, remember me saying that at that time I bore a strong resemblance to the young version of Al Pacino in in the first Godfather movie? And Pacino is what, now? That's right. He's Italian and there was my undoing because, while I looked like a nice, Italian guy, there is nothing Italian about me unless Austria, Poland and Russia count as Italian.

The next day, Monday, Anna got to school and excitedly told all her friends about the nice Italian guy she'd met. Her friends laughed and she naturally asked asked what was so funny. I know Steven. He was in my English Lit class and there's nothing Italian about him. Hell, he even likes Woody Allen movies.

So, now Anna had a big problem. Her late husband was Italian born and bred - a partner in the restaurant with her family, in fact. His share of the business. was now her share. As much as she hated the idea, she quickly came to realize that this new and wonderful relationship with me would never work out. It would even put me in danger if ... well, she sure as hell would never tell her father that a nice Jewish guy had fucked his princess in the ass ... even though her dad was safely spending the next several years in Sing-Sing, other parts of the family could assure that the family stayed Italian.

The next Tuesday night, she called me and explained that, even though we had had a great time and even though she was crazy about me, it wouldn't work out because of family pressures. Family pressures. It wasn't about me, she tearfully told me. It was her. It was her family.

I resolutely took my mid terms despite my grave disappointment and I did very well on them. Nonetheless in was in a numbing, blue funk. I revealed to Isaac, my oldest and most trusted friend, the source of my depression. I told him about the dinner, the sex and then the subsequent rejection.

"Shit, man!" He said to me, "you're one lucky bastard. You do know that? You do know who she is, don't you?"

"I, well, yeah. Sure. I guess so."

"And you know the name of the family restaurant? The (ahem) FAMILY restaurant. Didn't you ever ask her her last name?"

"Not .. that family!"

"Yes, that family. Consider yourself lucky ... well, luckier than the dead husband, anyway. You do know he was killed and didn't die choking on a meatball, don't you?"

"Very funny."

"Don't you ever read the News? Listen, just do yourself a big favor and NEVER mention that night to another soul. Ever"

And I didn't until now. I feel better getting it off my chest. Enough time has passed, I figure and the names have been changed as they say, to protect the innocent. Still, I have to admit that that night will always be a tough one to beat. In fact, whenever I go food shopping and see an olive oil container ...