Crushing

“Ready to go?” I said.

He kept smiling and opened one of the back doors, as if he was finally gifting me with something special. I got inside the car and then my heart started to beat faster. Jill was in the back seat. Her face was glowing, and her clothing was disarranged. She was barefoot. Vincent closed the door and my head started to spin.

“What…” I started to say.

“Quiet, Eric.” Jill said.

She slithered over to me and wrapped her arms around my neck. She smelled like flowers and felt very hot. I was still a virgin and did not feel it my place to take the lead with such and experienced girl. I think she knew this, and was willing to take charge here. Her lips were very slippery. I awkwardly bit her bottom lip, thinking this was the best way to make-out. I could feel her heavy breathing. My hands reached around her waist. She felt very soft. I noticed her belt was off. I was certain that paired with kissing Jill I was at least entitled to feel her boobs. My hands fumbled with the buttons on her blouse. She stopped kissing me and looked directly into my eyes as she deftly unbuttoned her blouse. She was braless. I wondered where her bra might be. Her pale skin was so comforting. Her tits were long, like her face, and skinny. They were heavy in my hands. I reached down and kissed her nipples. I licked her like a student conducting an experiment. Her skin smelled even better than her clothes. Instead of many flowers, the scent was of one particular flower. Her hand tilted my head upwards and we resumed kissing. My hands held tight to her breasts. They were keeping me anchored while a set of unfamiliar emotions invaded my reality.

Jill nibbled on my neck and made me feel so special. I was letting her do everything. She reached down and started to feel me through my pants. I wanted to unbuckle them, but was hesitant and let her proceed. She unbuttoned my pants and slid down the zipper. Jill gently teased the band on my underwear with a long nail, before finally tugging them down a bit. I felt her warm hand on my penis. I was very hard. She bent her head and took me in her mouth. Her tongue felt so friendly, so right. I was certain that my 6 inches or so was not the biggest she had ever had, but I was also sure it was worthy of her.

I mumbled something. I moaned. I was being treated so kindly, I thought. She was now using her hand at the base of the penis and working in unison with her talented lips. I waited for her teeth to make contact with me, but she was very experienced and not once did that happen. I was at her mercy, as she started to suck my dick like it was a lollipop. My neck snapped back and I banged my head on the window as I started to cum. This was my first assisted orgasm, and at that moment I could not have wished for a better partner. My load was explosive. Jill gagged for a second then regained her composure. I was startled. She swallowed the whole load.

Her blue eyes: primal and sympathetic.

She wiped away any cum that made it out of her mouth, but there was one spot that she missed. The image of her with my sperm on the corner of her mouth was indelible. I have used that as jerk-off material so many times since.

I flashed the headlights to let Vincent know we could go.

“You were great.” I said. “Thank…”

“Don’t say it. Don’t spoil it for me.” She said.

I looked at her with gratitude and was quiet as we waited for Vincent to get back. During the ride home Jill and I were silent. She was pensive and seemed satisfied with herself. Vincent was a little hyper, fidgeting with the radio, singing along with the music, and looking over to Jill. She smiled and looked out the window. I was just trying to relive the moment in my head. I did not feel spent. I wanted more from Jill, but felt that the night was over. As we got back to the party, I felt a sense of guilt. I really wanted my first sexual experience of any kind to have been with my crush, Olivia.

We dispersed inside the party, each going back to his routine. It was only a few moments before Vincent was leaving again. This time he picked a very pretty girl who only kept company with guys. It was as though she had an entourage of guys during the school day. And here was Vincent, taking her all to himself. I didn’t wait for an invite this time. I looked over to Jill, who just smiled at me. I shrugged and smiled back. She blew me a kiss.

I spent the rest of the weekend wondering if seeing Jill would be strange, if either or both of us would look embarrassed, but when I saw her as we were leaving the lunch room, she acknowledged me with a familiarity I had never know from a girl. I returned her friendly greeting. Her best friend even said hello to me. I did not feel shy about what had happened. It all seemed to flow naturally.

*****

As graduation was nearing, time seemed to be running out for any chance of ever getting to know Olivia better. She was in only two of my classes, but I had been in love with her since the first time I saw her: Sophomore year orientation. I only managed to speak to her a few times, and felt that we shared a certain similarity between us. She wasn’t among the ultra popular, but she had a very impressive persona. She had her boyfriend and did not seem willing to look elsewhere. He was a borderline drug addict with violent tendencies. I thought he was wrong for her, regardless of my feelings for her.

Olivia had curly brown hair, with a small patch of lighter brown hair at the top of her head. She was about 5’3″, with and athletic body, even though she did not play sports. Her hips were full. She had a very firm and high ass. Her chest was average, but seemed very proportionate and balanced. For having so many curves on her body, her stomach was completely flat. Olivia had tanned skin that never showed any blemishes. Not once in the 3 years that I saw her on a day-to-day basis did she ever have a pimple. Her voice seemed older and belied her cheerful appearances, as if she had already gone though high school and was merely putting in an encore appearance.

The prom had come and gone. I had decided not to go. I didn’t think of asking anyone. Jill told me she would cancel on her date if I wanted. I almost took her up on her offer, but regrettably said no. There was another girl, Jill’s best friend, who was of the same ilk, who hinted around that she needed a date. I knew it would have been a fun night with Lisa, who was 19 years old, but I was getting sick thinking about graduation and the idea I would never see Olivia again, so I decided not to go. Vincent actually went to two proms. He went to our prom, bringing some very hot woman. She was 20 years old and worked at some clothing store he went to. The following week he went to a prom with a girl from a rival school. His status as legitimate gigolo was forever cemented on those two nights.

On the last day of classes, two days before graduation ceremonies, there was an informal dance thrown together. I wasn’t going to go, but Jill told me that she wanted to dance with me once before saying goodbye to me forever. I agreed, and amid swirling thoughts of unrealized love, I went to the dance. I danced with Jill, who looked sad and happy all at once, and I danced with her friend Lisa, who whispered into my ear that Olivia had broken up with her boyfriend on the night of the prom. What did she know? I thought.

She laughed at me as I moved away from her. Her laughter had a slight mocking tone. Could I commence to fight a battle I thought was lost? Olivia! I stumbled over to a deserted part of the gymnasium. Out of the corner of my eye I saw Vincent heading towards me. He was walking with a swagger I had never known for myself.

“Eric, don’t forget, I am having an after dance party at my mom’s place. She is somewhere else tonight. Bring Jill and Lisa with you.” Vincent said.

“Really?” I said.

“Both those bitches. Jill likes making out with other girls while a guy watches, then anything goes.” He said.

“All right.” I said.

I walked over to where Jill was. She was standing next to Olivia, who looked sullen and not very comfortable. Olivia was wearing a puffy blue skirt and form-fitting top. She had on blue heels. Her hair was an incredible display of curls. Her sad brown eyes looked straight at me when I walked over to Jill. I nodded hello to Olivia, and then got Jill’s attention by tapping her on the solder.

“Hey.” I said.

“Eric!” She squealed. She was a little drunk.

She looked less attractive then usual next to Olivia.

“Vin is having a party at his mom’s place. She’s not around. Do you want to go with me? Bring who ever you want. Where is Lisa?” I said.

I made eye contact with Olivia. She was the one who I wanted to come with me.

“Olivia?” I said, as I reached down and gathered my courage. “Do you know where Vincent lives? Would…”

“Yeah. It’s on my way home. I was headed there for a minute or so. Maybe I will see you there.” She smiled, but did not let on anything else.

For the first time in high school I felt I had hope for something that I really wanted. All the failures of the past were ready to be washed away. Olivia was available and I was sure I was going to find a way into her life. We said good-bye for the moment.

I drove Jill and Lisa to the party. Jill was in the front with me and Lisa was in the back seat. They started to tease me about Olivia.

“What does she have that I don’t?” Lisa said.

“You and I have been intimate. How dare you. I am not sharing you with anyone.” Jill said.

“Yeah. And you and me are going to have sex, and I am not sharing you with anyone. Except Jill.” Lisa said.