It was summer in the early 1990s, and I was spending the semester studying in Rome. I had saved three years of summer and part-time job wages so I could pay my own way into this program. I was doing well in the classes. I loved the weather and the food in Italy. And I had a group of great friends.
My closest friend was Kit, and we did everything together. We went on weekend excursions to other parts of Italy, we took long walks around Rome and went dancing. I was coming off a break-up with my first serious boyfriend. I didn't want the guilt and burden of a long-distance relationship, and this was before you could videochat across the globe. I didn't even have an email account.
Everything was fine, but I started to feel lonely after Kit hit it off with Davis, a guy in our program.
Kit was hoping I would show some interest in Will, Davis' best friend. My initial take was that he was too shy. He was tall and thin, with sweet brown eyes and a messy mop of hair that he told me was his attempt to look like Eddie Vedder. I could tell he liked me, but he never made a move, and I wasn't sure I wanted him to.
As Kit and Davis made out on a train ride home from a trip to Florence, I sat with Will. I was tired, and it felt good to put my head on his shoulder. I eventually fell asleep and woke up nuzzled comfortably against his chest. He was growing on me.
We started to hang out more. His Italian was pretty good, and I would rely on him to order at restaurants and ask for directions. And, we were two of the only students in the program who spent much time studying. Sometimes we would sit on a bench not far from the pensione reading our assigned texts. I would take off my sandals and put my feet up on his lap. I liked the way he absent-mindedly rubbed my calves and ran his hands over my shins and feet. At night, he would help me pronounce Italian words. But he just couldn't make the move to kiss me.
People assumed we were a couple. Even Enzo, the pensione cook. One night, I was working on my Italian with Will in the kitchen as I helped Enzo prepped food for the next day. I loved to cook and sometimes he let me cut vegetables or make sauces. When Will went upstairs, Enzo said. "You shouldn't tease that boy, Lily."
"What do you mean? Maybe it's him leading me on," I replied.
Enzo said something I couldn't understand in Italian. Then in English, "You would be too much to handle for him."
I blushed and finished up whatever I was chopping.
All the straight girls had made jokes about Enzo when we first arrived. He was stereotypically Roman. With dark curls, a constant 5 o'clock shadow and a classic Italian nose. He moved with slow confidence. I couldn't tell if he was 25 or 35. He said little about himself. For the most part, he ignored every young woman in the house. He put up with me a little because I liked to help cook. I tossed in bed for a while trying to figure out why he thought I would be "too much" for Will. I wasn't experienced or confident. I had been a virgin six months earlier, and only had vanilla sex with my ex-boyfriend. I have never considered myself too much for any guy to handle.
I had promised to check in with my ex a couple times by phone that summer, so I called him one night from the phone in the hall of the pensione. I told him about my classes and some of our trips. He told me about his internship. We didn't have much else to talk about. I almost told him about Will, but what would I say? I was flirting with a shy guy who couldn't make a move? We hung up awkwardly.
I started crying after the call, and as I walked through the kitchen, I literally bumped into Enzo. His hands held my shoulders to keep me from losing my balance, and I looked down to hide my tears. He moved his hand to my chin and gently pushed it up, so I was looking into his dark eyes.
"Lily, why do American girls cry after they speak to their boyfriends at home?" he said.
"He's not my boyfriend anymore. But, I guess I'm crying because I miss him."
He shook his head. "I don't think so. I think you cry because you realize those boys don't miss you as much as you wish they did."
That stung like a cold ice pick into my heart. I blushed and ran to my room.
That weekend, our other roommates were on a weekend trip so Kit and I had the girls room to ourselves. Two of the three professors were also out of town, so everyone was ignoring the rules. Especially since Professor Pelli was the only adult in the place, and he usually drank two bottles of wine before 9 p.m. on weekends. Kit, Davis, Will and I had a great night walking around Rome. Will bought me gelato and held my hand. I told Davis that he could have the room with Kit that night. I showered, put on my best pair of panties and a long T-shirt, and padded up to Will's room.
"Will, wake up," I said. "Davis is in my room with Kit. Can I stay here?"
"Of course Lily," he said, his hair even messier than usual. I stood looking down at him, hoping he'd say something a little more enthusiastic. I was raised to not be too pushy, but I had not had an orgasm in weeks and I wanted to throw myself at him.
"It's colder up here," I said, even though it was 80 degrees outside and we had no air conditioning. Finally, he got a clue. "You can climb in with me."
I paused again and feigned reluctance, while trying to look cute. "Ok, but no funny business," I said.
I turned my back to him, and he spooned his long body around mine. He rubbed my shoulders and arms with his hand, and I encouraged him. "Mmmm. That feels nice."
He was thin and angular, unlike most of the stocky guys I had dated. I liked that he could envelop me with his long limbs, and that his hand could easily tickle me all the way from my neck to my leg. His hand brushed my outer thigh tentatively, and I pushed back into him to encourage more. I could feel his hardness against my ass and back, and he pulled back a little as if embarrassed. I kept scooting into him.
His hand began to linger from just above my knee and up to the bottom of my panties. Then he got the courage to tease the front of my leg, and his long fingers finally caressed my inner thigh. My body reacted hungrily. My nipples hardened against my shirt, and I clenched my legs together as I felt my lips open and dampen.
I arched my back against him, and he wrapped his right hand underneath my body and cupped my breast through the shirt. "Oooh," I said, pressing against his palm. I put both my hands in the air like a kid who needs help getting a shirt off, and he picked up on the obvious clue, pulling my shirt over my head. Men had been staring at my tits all over Italy for weeks, and I had a feeling Will would like what he saw. I sat up in the bed and turned to face him, my perfectly round, just turned-20-year-old perky tits pointed at him. My small, pink nipples erect and aching to be touched. He sat up and stared for a second. Finally, he took my face in his hands and kissed me. It was not delicate or skillful, but I liked that I could feel his desire through his lips and probing tongue. It felt good to be wanted that bad. I was proud that I had finally pushed this shy boy to take action.
While he kissed me, his hands explored my torso, starting at the top of my breast, his fingers briefly teasing my nipples, then running his palms over my flat stomach and around my ribs. The tops of his fingers paused as he felt the the spot where my panties met my hip bone, and the anticipation made me gasp. I was still sitting up and I needed to put my hands behind me to hold myself up while he kissed my face and neck and rubbed me slowly from my waist to shoulders.
Finally, his lips made their way down my shoulders, kissing my clavicle and then the top of my breasts. I could feel his breath on my nipples. He gave a nervous kiss to one nipple, followed by a long lick. I moaned loudly to let him know he was on the right track. Suddenly, Will found some confidence. He nibbled, licked and sucked each nipple, sending waves of pleasure down my spine. I could feel my folds opening and my clit swelling. I pressed my crotch against the mattress, desperate for friction. I put the back of my head down on the pillow and pulled him on top of me. His lips never lost connection to my nipples. I pulled his shirt up over his head so I could feel his bare chest against mine. For minutes, his mouth alternated from my breasts to my lips. I squeezed my thighs together around his leg, rubbing hard up against him and feeling his erection hitting just above my hips. I hoped he could feel my ardor and guess what to do.
My clit was throbbing, and I was desperate for him to pull my panties aside and touch me. If he simply slid that tongue down my body to my labia, to my clit, I would explode in seconds. I had guessed that Will was a virgin. But was it possible that he finished two years of college without ever giving a woman head?
His fingers slowly tickled my hip bone, playing around with the waistband of my panties. I reached down and cupped his balls through his boxers, then pressed my palm hard against his shaft, moving up and down against the sensitive underside of his penis. I spread my legs kissed his forehead, his temple, anything I could reach. I whispered. "Please."
His hand moved to my crotch, and he rubbed the growing wet spot on my panties with his index finger. My whole body opened up in relief and joy. I moaned loudly, and pressed my hand harder against his erection. He placed his finger underneath the fabric and explored my labia like it was a new territory. He ran his index finger from the bottom all the way around, reveling in my dampness. Then, his finger was inside me, pushing upward deftly. Every time he hit a new pleasurable spot, I moved my hand up and down the length of his cock, eliciting enough pleasure that he had to let go of my nipple for a second to gasp.