In my junior year, Steve became my main squeeze. But I found I had room for more squeezes.
Lookout Point
I looked in the mirror. I’d washed and blow-dried my hair, and I liked the way the long, blond curls framed my face. I was trying a new eyeliner. This blue should have made my eyes bluer, but it didn’t look like it was quite the right shade.
My nipples showed through the thin bra I’d bought last week. My mother didn’t know about this bra. All the ones she’d helped me buy had thick padding. She said I needed some uplift. I wanted one where I could feel a boy’s hands when he touched me. I hid this bra, so my mother wouldn’t find it like I hid the box of condoms. She knew I was taking the pill, but she thought I was waiting for the right boy.
I checked my purse. Three condoms should be enough for tonight. I went to the living room to wait. Mom was working in the kitchen preparing dinner, but she popped into the living room where I was waiting on the couch, checking for messages.
“Who you going out with?”
“Bill. We’re going to go to the drive-in diner. Sharon and Betty are going to meet us there.”
“Don’t you think you should go out with other boys?”
“Mom. We’re not serious. He’s just a friend.”
I’d been dating Bill for three months. We usually went out on Friday and Saturday nights. I’d told my mother that we were going to the diner. We did. We bought hamburgers, fries, and shakes and drove up to Lookout Point. We climbed into the back seat and talked about school while we ate. He was a senior and was worried about his college applications. I was taking my first AP course and having to work hard for a change. He finished eating first and moved closer. I was sucking up the last of my malt when he put his hand on my breast. He held me through my blouse for only a minute before sliding his hand down inside my blouse. He held my breast, squeezed gently, and rubbed my nipple through the thin nylon. I thought he was enjoying the feeling my hard nipple through the thin bra.
When he started to unbutton my blouse, I felt the warmth growing between my legs. I already wanted him to touch me down there, but I’d wait, let him take his time, and let the feeling build. He pushed my blouse back; I pulled it over my shoulders and lifted my arms out. He played with my nipples through the sheer material. I liked this bra a lot. When he put his arms around me to undo the bra, I leaned forward. He slipped the bra off my shoulders. The fresh air on my breasts made my nipples harder. I pushed my chest up, and he understood that I wanted him holding me and rubbing my nipples.
I closed my eyes and laid back so I could concentrate on the pleasure. The desire from my crotch kept growing. I was thinking about pushing his hand down there when he bent over, put his mouth on my nipple, and slid his hand up the inside of my leg. Oh, how I wanted him to do that! I thought he was about to touch my mound, but he ran his hand down the inside of my other leg. I moaned. I hadn’t meant to do that; it came out on its own.
He lifted my dress. I undid the button, pushed my skirt and panties down over my knees, and stepped out of them. I opened my legs as wide as I could. I wanted him to rub my clit, or lick it, or put his penis in me. He pressed on my mound with his whole hand. I wiggled and pushed back.
Opening my eyes, I realized that he was still fully clothed. I unbuttoned his shirt and pushed it off his shoulders. He let it drop, undid his pants, and slid them down. Before he could get them completely off, I pulled down his underpants, freeing his hard rod. I held his hips, slid my hands around to his hard bum, and pulled him to my mouth.
I explored the head of his penis with my tongue. He pushed farther into my mouth. I sucked him in until he pressed on my throat. I’d only taken a penis in my throat a few time, but right now, I wanted this hard one in my vagina.
I picked up my purse, took out a condom, tore it open, and pulled out the rolled plastic ring. He held his rod while I rolled the slick plastic down. I made a fist around his rod and tightened the plastic.
I turned and put my knees on the seat. Bill knew that I wanted him in me and wasted no time. He held my hips and put his rod on my opening.
That hard penis was what I needed, wanted, had to have. My body shook as soon as he touched my vagina with his tip. I moaned as he slid in me. He started thrusting, and the heat grew. I pushed back hard as he thrust. I wanted him as deep as he could go. My mind was wholly in my vagina, feeling the pressure as he moved in me. Oh, the deep pressure. More, more pressure. Faster. Yes, just like that.
I cried out as a wave passed up my body from deep inside. He kept up the pace, another wave. He sped up—another wave. He pressed hard and pulled my hips. His body shook.
He’d brought a towel, and I sat on it. He hadn’t put any cum in me, but I was so wet I needed something. He wasn’t completely soft, but the condom slipped off easily. I sipped my shake. It wasn’t completely gone, but I was soon slurping air. I popped the plastic top off the shake and put the baggy condom in it, replaced the top, and set the cup on the floor.
We talked about the college trip he’d taken with his mom while we sat naked. He held and played with my breasts. He and his mother had stopped in New York, visited the Met, and saw a show on Broadway. Maybe mom and I could do that next year.
I took his penis in my hand. He rubbed my nipples. I pushed him back. He lay on the seat with his knees up. I climbed over him so that I could lower my bush onto his mouth. As soon as his tongue touched my clit, I twitched. He tongued me back and forth and around in circles. The heat was rising. I bent over and took the end of his penis in my mouth. As he tongued me, my mind focused only on my clit. The pleasure built until it overflowed, and my body shook.
He was hard again. I put another condom on him and turned around so I could lower myself onto him. In this position, he rubbed my clit every time he thrust into me. He lasted long enough for me to come twice before he pushed up and held himself in me and cried out.
We had brownies for dessert. While I ate mine, I held his limp cock and rubbed it. I finished my brownie and licked the chocolate off my fingers. He was still soft. I pushed him back and knelt so I could lick his member. It started to swell up. I ran my lips back and forth on the head as he swelled up. I liked my hand and stroked the shaft, but I didn’t want him to get too much into being sucked because I wanted him in me. He’d be able to keep going for a while on the third time. But the feel of his penis on my tongue and him sliding to the back of my throat was so good. When his hips pumped up, I realized I’d better stop.
I laid across the seat with my left leg on the seat back and my right leg up against the back of the front seat. This was as wide open as I could get in the car. We’d been able to use his bed at home twice when his parents went away for the weekend, and I’d loved being able to pull my legs back and watch him pound in me, but with his legs bent up behind him, he could push deep in this position.
Bill played basketball and had an athlete’s physique, blond hair that always looked like he’d just stepped out of the shower, and a strong jawline that had only a light beard tonight. He’d started out slow, but was speeding up. I matched each of his thrusts, pressing my clit on his mound with each one. My focus shifted, and I no longer saw the man who hovered over me with his body surging with each thrust. I felt his hardness in me, felt him press my clit, died when he pulled out and lived when he pushed in.
The wave came from deep inside. My body shook. I held him. I don’t know what I cried out. All I know is that he kept up the hard, fast thrusts. Then it came, the second orgasm right after the first. I clinched him as tight as I could, knowing that I’d make him come. And he did, pressing into me with his hips jerking.
We lay together for several minutes. I didn’t want him to, but he softened and slid out. Then we were all arms and legs in the wrong places as I tried to sit up; he banged his head on the roof and leaned hard on my leg. We eventually got it all straightened out and sat naked next to each other. I slid the third condom off him, dropped it into my cup, and clicked down the plastic top.
“We getting together after school on Monday?” he asked.
He’d been giving me a ride home after school for the last two months. We’d stop off and have sex almost every day. We had a usual place. We’d hop into the back seat, pull off our clothes, and he’d be in me right away. Thinking about it had me wet by the time he parked the car.
“Sure. Why’re you asking?”
“You said you were going out tomorrow.”
“It’s just to a movie.”
“You’re going with Steve.”
“You said you didn’t like musicals.”
“You going to let him touch you?”
“That be okay with you?”
“I don’t know. I sorta thought we had a steady thing.”
“We do.”
“Then why would you let him touch you?”
“What if he wants me?”
“You mean, have sex with you?”
“Yes. Would that be okay?”
Bill sat back, looking at his hands on his knees. I thought about breaking the silence, but there was that question hanging in the air. I wasn’t sure I wanted to be with Steve. He was a jock like Bill: tall, strong, and a good dresser. Barbara had gone out with him and wanted him to ask her out again. She hadn’t been happy about answering my questions about him.
“I sorta want you for just me,” he said without looking up.
“You graduate in two months, and then you’ll go away next year. We’re having a good time.”
“Am I just a good time?”
“You know I like you a lot.” I leaned over and kissed him. He looked up, but he was quiet and stayed that way while he drove me home.
On Saturday, Steve took me for a quick meal near the movie house. We got seats in the middle of the theater with a perfect view of the screen. About halfway through the show, he put his arm over my shoulder. A bit later, he rubbed his hand along my neck. Maybe it was just that he was new, or maybe there was something there, but I felt the warmth between my legs and knew I was getting wet. I leaned toward him, letting his hand slide under the edge of my blouse.
I watched the movie, but a part of my mind noticed his other hand cup my breast, rub his hand on my leg over my skirt, and slide his hand under my skirt and along the inside of my leg. As he ran his hand along my leg, the heat in my crotch grew. When he pressed on my mound through my panties, I twitched. He started to slip his finger under my panties. I stopped him. If he did that, I’d miss the end of the movie. Rubbing me through the cloth might be too distracting, but he pulled his hand back. I let him unbutton my blouse so he could touch my breast through my bra. I’d worn my special bra, and my nipples responded to his fingers.
While we were walking to the car, he said, “It’s early. Want to go up to Lookout Point.”
I’d been thinking of exactly that. “Sure.”
I suppose I’d known this might happen. I’d put four condoms in my purse. We used them all. Being with Steve wasn’t better than with Bill, but it was different. It was the same moves, but sometimes he went a little faster than Bill, sometimes he pressed me softer, and sometimes it just felt different. When he walked me to my front door, he asked me out the next Saturday. I said, yes.
I didn’t see Bill until lunch on Monday. We were with a group and didn’t have any time alone, but as soon as I got in the car after school, he sat still and looked at me.
“What?” I asked; even though I knew the question that was waiting.
“Did you have sex with Steve?”
“Yes.”
“Where did you go?”
“To Lookout Point.”
“So you had sex with him just like you did with me the night before.”
“Pretty much.”
He started the car and drove in silence to our special spot. It was in a park that had a trailhead with only four parking spaces. Hardly anyone used the trail during the weekdays. As soon as he shut the engine off, I got into the back seat. He sat behind the wheel.
He turned to look at me. I took my clothes off and sat on the seat naked. I laid across the seat and spread my legs. He started to turn toward the front but turned back. I put my hand on my bush and rubbed my clit. I closed my eyes and concentrated on the rubbing. I heard the car door open and close. The back door opened. I felt his eyes on my crotch. I spread myself wider open. He came in the car and closed the door. I kept my eyes closed as I heard and felt him undressing. He leaned over me and entered me.
I could feel his anger as he banged hard. He held my shoulders so he could pull me to him as he cried out with each thrust. He didn’t wait to let the feelings build for me, and he hadn’t put on a condom. This was the first time he came in me without one.
He was still silent as I wiped up his cum with a Kleenex and then dressed. I went back to the front passenger seat and waited. After a few minutes, he dressed and came back to the driver’s seat. He started the car and drove toward my house.
“I don’t like you having sex with Steve,” he said.
“I want you every day,” I said. “You still want me?”
After two blocks, he said, “You know I do.”
“I’m going out with Steve next Saturday.”
He pounded on the steering wheel. “Damn.”
We resumed our regular situation. Bill took me home after school, stopping along the way, and took me out Friday nights. But Steve became a regular on Saturdays. My mother was pleased with this change because she’d thought I was getting too serious with Bill. Bill and Steve graduated. Bill and I saw a lot of each other during the summer, but I had a job so we couldn’t do much during the week. He often picked me up after work, and we’d go to our special place. Steve continued to be my Saturday night date except for a few weekends when Bill and I went to the beach.
At the end of the summer, they both left for college. I returned to school as a senior. I couldn’t decide if I’d have a steady or take my chances and visit Lookout Point with several boys. It turned out that several boys was the answer because I didn’t find anyone I wanted to spend every weekend with. Both Bill and Steve came back for the holidays, and we renewed our friendships for two weeks.
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