All characters in this story are eighteen-years-old or older.
I was never the prettiest or most popular girl in school but I had a small circle of friends including my best friend, Diane. Diane was far more popular in school than me, especially with the boys. She was pretty, outgoing, and always seemed to have a boyfriend. Me, on the other hand, had only been on a couple of dates but nothing extraordinary ever happened. Maybe that’s why Diane and I got along so well, we were almost complete opposites.
Diane tried helping me with the boys but things never seemed to work out. The boys that were interested in me weren’t my type, whatever that was and the boys I was attracted to didn’t want anything to do with me. I was fine with that. I would spend my free time with the few friends I had and was happy. Even though I say I was happy, I think I just accepted the fact that boys didn’t find me attractive. I didn’t have a lot of confidence and had body image issues like most young women.
I’ve known Diane since grade school; she was older than me by a couple of months. Her birthday was early in the school year and mine was in January so we were usually the oldest kids in our class. She was way more adventurous than me while I was mostly a scaredy cat and afraid to take chances. Any time I got into trouble, you could bet that I was with Diane. I admired her risk-taking and she did help to teach me to be less cautious and to try new things.
Shortly after I turned eighteen, Diane told me that for my birthday she was going to find me a boyfriend. She told me I was single for too long and now that we were in our senior year, it was time for me to come out of my shell. I laughed at her but didn’t discourage her either. The first thing she did was take me shopping for some new clothing.
She would always tell me, “You have a cute little body. You have to start accentuating your assets.”
Diane had my mom get me several gift cards to some clothing stores for my birthday and we spent the entire day at various stores trying on clothes and buying a new wardrobe. My best friend convinced me to get out of my comfort zone of wearing only jeans and sweatshirts. By the end of the day, I had several new tops that consisted of tank tops, crop tops, and some camis. She also convinced me to buy a couple of pairs of leggings and shorter skirts than I was comfortable with. I also bought a couple of bra and thong sets.
We even had a sleepover at Diane’s house that night where we put on makeup and she gave my dark brown hair blonde highlights. She snuck a few of her dad’s beers up to her room where we talked about going away to college and boys. Diane was currently dating Mike and I knew she was no longer a virgin. She was telling me how great sex was and how she lost her virginity on her eighteenth birthday. I had nothing to compare it to other than using my hand and fingers and watching an occasional porn flick.
As we were having our girl’s night, Diane mentioned to me, “We have to get you laid, Carly. You’re eighteen now.”
“There’s one problem with that, Diane. I have to have a boyfriend first.”
“If you follow my lead, we’ll fix that problem. Your new hair color and a touch of makeup will help. When you start wearing your new clothes, the boys will notice so that won’t be a problem.”
“That’s easy for you to say, you have a great body. Boys barely know I’m alive.”
“Trust me, we’ll fix that. Besides, I’ll talk to Mike. His friend, Dan, just broke up with his girlfriend and is available.”
“Dan is cute but he would never go out with me.”
Diane shook her head in pretend shame, “Didn’t I just get done telling you to trust me?”
“Okay, okay.”
We talked well into the early morning hours with Diane telling me about giving hand jobs and blow jobs. Mike was pretty good at licking her pussy too. She said sex was even better but to make sure we used protection. I told her I didn’t think a guy would want to go out with me because my breasts were too small and my butt was too big. We were feeling buzzed from the beer we drank and Diane told me to take off my nightie and panties. We stood naked side-by-side before her full-length mirror.
She got behind me and cupped my breasts and said, “See you have nice tits. They aren’t much smaller than mine.”
Diane then had me turn around and we compared our butts.
“See, they’re about the same size. You just need to start showing off your booty more. Be proud of it.”
“You might be right, Diane, but I’ve only been on a few dates and haven’t made out with a guy. I’m not even sure I’d know what to do.”
“You worry too much. Just do what comes naturally and you’ll be fine.”
That Sunday, Diane came over to my house and picked out the clothes I’d wear to school the next day. We started with a simple pink tank top and my new black leggings. A push-up bra made my breasts look bigger and enhanced my cleavage. The thong made sure there were no panty lines in my leggings and helped define my ass cheeks. Monday morning at school, I thought I noticed some boys looking at me differently. Maybe they didn’t like my new clothes but Diane assured me otherwise. That’s when Mike and Dan came up to us and I saw them looking at me like they were undressing me with their eyes.
Mike was the first to comment, “Wow, Carly, I like the new look.”
“Yeah, you look great,” Dan added.
Diane smiled at me with a grin that said, “I told you so.”
The guys followed us to class and as we were walking, Diane whispered to me, “Bend over at the waist to pick up your books.”
I was confused because I was holding my books when Diane reached over and knocked them out of my hand. Now I knew why she did that. I bent over at the waist and stuck my butt up in the air. As I was picking them up, I saw Dan and Mike checking out my ass. That made me feel great. I noticed some of my teachers checking me out too which gave me a rush of excitement. Maybe Diane was right after all.
My best friend was trying to fix me up with her boyfriend’s best friend whose girlfriend had just dumped him. I had a crush on Dan for a long time but he always had girlfriends that were much prettier than me so I figured I would never have a chance to date him. He was so cute, my heart would beat faster whenever I saw him. Both he and Mike were on the baseball team which made them very popular
It would get excited when Dan would smile and say, “Hello Carly,” when he saw me in the hallway in school. I was happy that he knew I existed.
When Dan asked me to go to a movie with him, part of me thought it was a practical joke. I couldn’t believe he would ask me out even though Diane said she would arrange it. I was naturally excited and went searching for Diane to tell her the good news. I had never been so happy in my entire life. One of the cutest guys in school just asked me out.
When I told Diane, she gave me a knowing look and said, “I told you to trust me, didn’t I?”
“Yeah, but I never thought it would happen.”
“You need to have some faith in me. Now, we have to get you ready for your date.”
Diane came over to my house late Saturday afternoon to help me get dressed. She picked out a low-cut yellow tank top that showed off a lot of cleavage and a very short blue mini-skirt.
I told her, “If I wear this won’t it send him the wrong message? You know, that I want to turn him on.”
“Oh my god, Carly. You’re my best friend but sometimes you’re so naive. That’s exactly the message you want to send him and you want to turn him on. If you want my help, you need to follow my advice.”
“Okay, okay.”
I was scared to death by the time Dan picked me up. I found it hard to believe a guy so cute wanted to go out with me and I didn’t want to ruin this chance. When he picked me up, he gazed over my body. I was terrified he wouldn’t like what I was wearing but my fears were unfounded.
“You look great, Carly. I wish I would have asked you out sooner.”
I was so relieved to hear that and secretly wished he would have asked me out before too. I thanked him and he escorted me to his car and opened the door for me like a true gentleman. I made sure to keep my legs tight together so I didn’t flash my panties at him. My skirt did ride up further on my thighs when I sat down and exposed more of my thighs than I wanted even after I tried to tug it down.
Dan took me to a sit-down pizza place for dinner before we went to a movie. I didn’t care where we went or what movie we saw as long as I was with Dan. I can barely tell you the plot of the movie we saw. He put his arm around me several minutes after it started and I just about melted in my seat. All I could think about was how good it felt to be held by him. It was impossible for me to concentrate on anything else. When the movie was over, all I could think was that I didn’t want the night to end.
Dan asked me, “What do you want to do now?”
“I don’t know.”
I started to panic when he suggested, “We could go up to the lake and uh, talk.”
The lake was a local lover’s lane at night and I knew that he didn’t expect much conversation but I didn’t want the date to end and I didn’t want it to be our one and only date so I replied, “Uh, yeah sure. We can go to the lake?”
I had heard of what some of the other girls did up there and I wasn’t prepared to go that far. We were both eighteen but I was still a virgin and was caught off guard by his suggestion but I desperately wanted to make out with Dan. It would be a dream come true. I was super nervous as we drove to the lake. I worried that he wouldn’t like the way I kissed. I wondered if my breath was okay. What if he wanted to have sex but I didn’t, would he ever ask me out again?
Once we arrived at the lake, there were a few cars already there so he parked far away from them. Dan shut off the engine and I was now facing the moment of truth. The suspense of what this evening would bring was killing me. It was like a life and death situation for me and my dating future. I desperately wanted to continue to date Dan but I wasn’t ready to lose my virginity the first time we went out.
We talked for a few minutes. I think Dan knew I was nervous and was helping me relax. When there was an awkward moment of silence, he leaned closer to me and kissed me full on the lips. It was simply amazing. A bolt of excitement shot through my mind and body. Finding no resistance from me, Dan continued to kiss me. We even began to French kiss. I had never been to the lake at night with a boy and I hardly had any experience even kissing one. I was excited beyond my wildest dreams to be there with Dan.
I got even more nervous when he asked me if I wanted to get in the backseat where we would have more room. I felt some pressure from him to agree but I also felt some peer pressure from not wanting to tell Diane I abruptly ended our make out session. I promised her and myself that I would try and loosen up and have some fun. I now had that opportunity. Besides, I was with my crush and was feeling sexually excited myself. My body was telling me I wanted more.
While we continued our passionate make out session in the backseat, I felt Dan place his hand on my breast. My first instinct was to stop his advances but it felt so good and I didn’t want the night to end so I let him continue touching my chest through my clothes. Before long, he slipped his hand up my shirt to fondle my breasts through my bra. I was wearing a lace bra so there wasn’t much material separating his hand from my breasts. My pussy was getting wetter the more we kissed and the more he touched me. I was afraid of where this was leading but I was having too much fun to stop him either.
I could tell Dan had a lot of experience making out with girls when he reached behind my back and unsnapped my bra with one hand. He then brought it around to touch my bare breasts and tweak my nipples. No boy had ever touched my bare breasts before so this was new territory for me.
It felt too good to stop him when he began to suck on my nipples. I could feel a dampness building in my pussy, an excitement to an extent that I’d never felt before. I was nervous and wanted to stop him but I was also having too much fun. However, I wasn’t ready to lose my virginity, especially in the backseat of a car.
Dan slipped his hand up the back of my skirt and began to fondle my ass with him telling me, “You have a nice ass, Carly. A lot of the guys think so too.”
“I always thought it was too big.”
“Heck no, it’s gorgeous, just like you.”
Dan was making me feel sexy. No one had ever made me feel that way before. Things were heating up as his hands were all over my body as we continued to kiss.
Another charge of excitement shot through my young eighteen-year-old body when Dan slid his hand up my skirt and touched my pussy through my panties. I pushed his hand away but he would slowly slide it back up between my legs to touch me again. I pushed his hand away a few times before I gave in to his advances and my own urges and let him continue to touch me there.
We were both breathing hard and French kissing. Part of me still wanted to stop Dan from going further but I was finally making out with a cute guy at a secluded lover’s lane and it felt wonderful. I heard all of my friends talking about making out by the lake and now I was finally experiencing it myself. Besides, I was afraid he wouldn’t ask me out again if I didn’t let him at least touch me.
When Dan pressed his finger into my pussy through my panties, it made me excited too. When I didn’t stop him, Dan took my hand and placed it on the outside of his shorts. It was the first time I felt a guy’s penis which meant it was the first time I felt an erection. I knew things were progressing faster than I expected and didn’t know what to do. Dan worked his hand inside my panties and was now fingering my bare pussy. Things were getting hotter by the second.
In a few short minutes, Dan asked, “Do you want to, you know, do it?”
“No Dan, I’m not ready.”
“Aw, come on Carly. I know you’re as hot as I am. Your pussy is soaking wet.”
“I know, but I’m still a virgin and I don’t want to lose my virginity in the backseat of a car.”
“How about a handjob then?”
I thought about it for a moment figuring he was all worked up and I wanted to continue to experiment sexually. I had already done more than I ever had before so nervously I replied, “Sure. I’ll do that.”
Dan scrambled to pull off his shorts and underwear and I got my first live look at a guy naked from the waist down. He placed his hand over mine and guided it to his hard-on. I nervously grasped his hard meat and followed his lead as I began to stroke it. I noticed a clear drop of some liquid coming from the head of his dick as I looked at it. The head was wider than his shaft and I looked at the ridge separating the two. His shaft had several veins running through it and what looked like a long muscle or something running along the middle.
His balls were covered with a thin coat of pubic hair and looked like walnuts covered by skin. Dan continued to fondle my breasts and finger me as I continued to masturbate him. I have to admit that I was tempted to let him fuck me but I was already nervous at giving him a hand job.
I got even more nervous when Dan said, “Do you want to try sucking it?”
I shook my head and said, “No, not tonight.”
He didn’t press it any further and figured he wanted to at least ask for a blow job. When his breathing got heavier and he closed his eyes, I sensed he was close to cumming.
That thought was confirmed when he said, “Faster, stroke me faster.”
I did as instructed and moved my fist faster around his hard dick and seconds later his white gooey sperm shot out of his dick like a geyser, covering his dick and my hand. He was grunting and groaning and I had a certain amount of pleasure out of making him cum. After he was done, Dan reached down to the floor of the backseat to get a rag and wiped himself clean. I used the same rag to wipe off my hand too. Dan put his shorts back on while I put on my bra and adjusted my clothing before he took me home.
As he was kissing me goodnight on my porch, Dan asked, “I had fun tonight. Do you want to go out again sometime?”
“Sure, Dan. I’d like that.”
As soon as I got in my room, I began to send Diane text messages about what happened with Dan.
“After the movie, Dan took me up to the lake. We were making out and I ended up giving him a hand job.”
“Why didn’t you fuck him, Carly? You had your chance?”
“I don’t know. It was our first date and I didn’t want to seem easy. Besides, I’m still a virgin and when I think about doing it for the first time, I figured it would be in a bed. Not in the cramped backseat of a car.”
“You could have given him a blow job.”
“He asked me to but I have never done that either. I guess I was scared that I didn’t know how to do it and he wouldn’t like it.”
“LOL, Carly. A guy never complains about a blow job.”
“I don’t know. He wants to go out again so maybe next time.”
Now, that I had gone that far, Diane was coaching me on taking the next step. Dan had asked me to dinner on Thursday night. I told Diane I was nervous about what Dan expected from me. I didn’t want to lose the only boy that wanted to go out with me. I went to Diane’s house on Wednesday night to study for a test the next day but she spent some time talking to me about my options.
“Well, one thing for sure, Dan is going to expect you to at least give him another hand job. That ship already sailed so you can’t go backward from there.”
“That’s what I figured.”
“You could go a little further and give him a blow job.”
“I know but I’ve never done that before either. I wouldn’t know what to do.”
“It’s easy. Wait here, I’ll be right back.”
Diane came back with a couple of bananas and I had to laugh. We peeled the bananas and my blow job lesson started. Diane taught me how to begin by licking it before taking it in my mouth. I was instructed to open my mouth wide enough so I didn’t scrape his dick with my teeth. I then practiced taking it deep into my throat. I was able to work on taking it deeper and deeper before I gagged but I still wasn’t sure I could get all of Dan’s dick into my mouth. Diane told me I didn’t have to deep-throat him the first time and instructed me on how to bob my head while wrapping my tongue around it. She told me I could tongue and play with the head while catching my breath before bobbing my head again. I wasn’t sure if I was going to blow Dan or not but I felt a little peer pressure from Diane to keep experimenting with my sexuality.
I naively asked Diane, “What do I do when he’s ready to cum?”
“I’ll tell you right now that guys love it when a girl swallows it or if you don’t want to do that, you can always let him cum on your face.”
“Eww. I don’t think I could let him cum on my face. What does cum taste like?”
“It has kind of a bittersweet, salty taste. It’s not that bad. Make sure you have something to wash it down with,” Diane said with a giggle. “It will definitely leave an aftertaste in your mouth.”
I still wasn’t sure I could go through with blowing Dan but we were having fun and he was turning me on more than I knew was possible. I liked the fact that a guy found me attractive and I’d never felt as hot in my life like when we were kissing and he was touching and fondling me. It was even better when he sucked on my tits. If that felt good, my pussy was on fire when he would finger me. I felt naughty too because I didn’t want my parents to find out what I was doing with Dan. I was taught that I should wait to lose my virginity to the right guy and I wasn’t sure if Dan was that guy.
On my next date with Dan, I wore a camisole without a bra underneath a blouse that I left unbuttoned. This way, I could hide my breasts and maintain some modesty but it would give my date easy access to my breasts. I wore a jean mini skirt for that same reason. We went to dinner at an inexpensive local restaurant. Dan kept telling me how pretty I was and he liked that I was easy to talk to, not like other girls. He made me feel good about myself and I was falling deeper for him the more we talked.
Dan had a nice smile and was on the baseball and basketball teams so he had a nice athletic body with broad shoulders. He was super cute and I couldn’t believe he would even go out with me but I was excited that he asked me out again. I was feeling better about myself and felt attractive for the first time in my life.
When we were done with dinner, Dan asked me what I wanted to do and I replied, “I don’t know. What do you want to do?”
“Well, we could go up to the lake again. It’s a nice night out and there’s almost a full moon.”
“Yeah, sure. Let’s go.”
On the drive to the lake, Dan would take his eyes off the road temporarily to sneak quick peeks at me. I felt a little self-conscious because I knew he was hoping to get laid but I wasn’t ready yet. Part of me wanted to have sex out of curiosity and wanting to lose my virginity to get it over with. However, I wanted that first time to be special, not some quickie in Dan’s backseat.
As soon as we got to the lover’s lane, we noticed a couple of other cars there that belonged to some of our classmates so Dan made sure to park far enough away from them to ensure our privacy. We then got into the backseat and immediately began to make out again. He didn’t waste any time touching my breasts through my camisole. My nipples immediately got hard and poked out through my top. He took off my blouse and lifted my hands over my head so he could take off my camisole. Now that he exposed my breasts, he began to alternatively suck on my nipples while he stroked my legs and fondled my ass.
I was getting hotter by the second, a fact not lost on Dan. He would stop sucking on my tits and kiss me some more before returning to play with my tits. His hand naturally found its way between my legs and found no resistance from me this time as his fingers probed my pussy through my panties. My pussy was wet and must have leaked onto my panties so Dan knew I was turned on too. I got a little bold myself and began to stroke his hard cock through his shorts. I didn’t realize that would send a signal to him that I might want to go further.
“Do you feel like doing it tonight, Carly? We’re both so turned on, it only seems natural.”
“I don’t think I’m ready yet, Dan. I’m sorry but I don’t want to lose my virginity in the back seat of a car.”
“That’s okay, I understand,” he replied but I could clearly see he was disappointed.
“We could, you know, do what we did last time though,” I said to offer a compromise.
“Sure. That would be cool.”
I was happy to give him another hand job but I could hear Diane’s voice in my head telling me I should blow him but I didn’t want to promise that. I wasn’t sure I could go through with it.
Dan pulled off his shorts and underwear and looked at me to signal that he was ready for me to start. I swallowed hard as I took his erection in my hand and began to slowly stroke it. His precum immediately appeared on the head. I was staring at Dan’s hard cock as I squeezed and played with it. I wanted to try sucking it but I was scared. I was afraid of what it would taste like. What if I didn’t like it? He would expect me to continue. I knew once I started I couldn’t stop.
Dan must have seen me staring at his dick and said, “Try sucking it. Go ahead.”
“I don’t know, Dan.”
I wanted to but was afraid.
“Go on. Suck it. If you don’t like it you can stop.”
His statement that I could stop if I wanted to took away one of my fears. I continued to stare at the hard dick in my hand trying to gather up the courage to go further.
“Go ahead, suck it, Carly.”
I could hear Diane’s voice in my head saying, “Go on, do it. What are you waiting for?”
I leaned down and ran his dick across my lips. I then gave the head a light lick with my tongue. I was trying to gather up the courage to put it in my mouth. Finally, I shrugged my shoulders figuring I should just go for it. I lowered my head, sticking out my tongue to guide Dan’s cock into my open mouth. His dick slid along my tongue as I wrapped my lips around it and began to bob my head.
“That’s it, baby. Oh yeah, that feels great.
Now that the initial deed was done, I found that his dick didn’t have a bad taste at all. It hardly had any taste at all. I swirled my tongue around the head and took him as deep into my mouth as I could. I gagged at first but continued to suck on the first dick to enter my mouth. Dan kept giving me words of encouragement while continuing to fondle my breasts. With each downward movement of my head, I tried to take more and more of Dan’s cock into my throat but I still couldn’t take it all. He didn’t seem to mind as long as I kept blowing him.
I remembered Diane’s advice to lick and play with the head while I caught my breath. It also gave me time to gather my thoughts now that I was sucking on my first cock. I decided I liked blowing Dan and giving him pleasure. The more I pleased him, the more turned on I got. I wanted to give him a good blow job even if it was my first time. I figured he probably had gotten blow jobs from his previous girlfriends so I felt some pressure by being compared to them. I wanted to be better than his other girlfriends. I didn’t want him telling people that I gave bad blow jobs.
Hearing Dan’s soft moans let me know he was enjoying my cocksucking abilities. Maybe I was a natural cocksucker. I kept my soft wet lips wrapped tightly around his shaft and made sure to keep using my tongue. As his breathing became more intense, I remembered being concerned about his approaching orgasm. Diane said I should swallow it but he came so much when I gave him a hand job, I was afraid I wouldn’t be able to take it all in my mouth. What if I didn’t like the taste? What if I got sick from it? I didn’t want to ruin it. Maybe I shouldn’t swallow it seeing it was my first time.
It didn’t matter what I thought because just before he came, Dan clutched my head and thrust himself deep into my throat, and announced, “Oh shit, I’m gonna cum.”
My heart was racing as the first wad of cum shot into my mouth. Before I could decide if I liked the taste of his cum, another wad quickly shot into my mouth followed by another and another. I swallowed as much cum as I could before he shot more into me. I had now decided it didn’t taste that bad and swallowed the rest of Dan’s load. I kept his dick in my mouth until he was done cumming and he released my head from his firm grip. I lifted my head from Dan’s lap and looked up at him for a reaction.
“Damn Carly, I can’t believe that was your first time. That was a darn good blow job. You’re a natural.”
I smiled with pride and said, “I’m glad you liked it. I tried my best.”
“Do you want me to do you now?”
“Huh?”
“You know, go down on you. You did me so I should repay the favor.”
“Uh, yeah sure, Dan. I guess so.”
Diane didn’t prepare me for this but I’ve heard nothing but good things about oral sex from the other girls. Dan laid me back on the backseat and reached under my skirt and began to tug at my panties. I lifted my ass off the seat so he could take them off and pulled them over my legs. I was a bit embarrassed to have him see my naked pussy. He understood and smiled before the slowly pulled my legs apart. He had fingered me before but never got a close-up look at my pussy. As my legs slowly parted, I got excited at the thought of him seeing me. Dan took a moment to gaze at my pussy. I blushed as he got down and began to kiss his way up my thighs. I didn’t know what to expect. I had masturbated before and fantasized about a guy eating my pussy but now it was about to become a reality.
I felt so vulnerable with my legs spread wide open with a guy being so close to my exposed pussy. No other person had ever seen me up close and personal like this before other than my doctor. When Dan’s tongue touched my pussy lips I knew there was no turning back. He spread my lips apart and stuck his tongue deep inside me. It felt wonderful to have someone tongue fucking me but it felt even better when his tongue brushed across my clit. I let out an audible moan as he flicked his tongue across it several times sending shockwaves of pleasure through my body. I clutched the back of his head, pulling him into me while lifting my hips.
Now that Dan was focusing on my clit, I knew it wouldn’t be long before I came to orgasm. I never wanted him to stop eating me. I came to the most intense orgasm I ever had. It was nothing like the one I got from masturbating. Wave after wave of sheer pleasure shot through my pussy and throughout my body. He had me squirming in the back seat in sheer ecstasy.
When Dan lifted his head from between my legs, he had a grin on his face and a glaze of my juices around his lips and he asked, “Well, what did you think?”
“That was awesome, Dan.”
“I knew you’d like it.”
When Dan sat up, he had another erection. If he would have pressed me, I probably would have fucked him because I was that turned on. However, he asked me to suck his dick again which I gladly agreed to do, especially after he just gave me the best orgasm of my life. I was able to enjoy blowing him more this time because I wasn’t as nervous. I found that I enjoyed having his dick in my mouth and giving him oral pleasure. According to Diane, it was the next best thing to fucking a guy. It took Dan longer to cum a second time which gave me more time to enjoy sucking his cock and experimenting with my tongue and lips. He was more vocal in telling me what he liked too. I had no problem taking his second load which I also gladly swallowed.
Dan ate my pussy again, too. I was more relaxed about spreading my legs this time. Hell, I was looking forward to it. He finger fucked me while teasing my clit which I found more pleasurable than the first time. I had never cum twice in one night, even while masturbating. When I got home, I immediately sent some text messages to Diane to give her a blow-by-blow description of what happened on my date with Dan.
“I just got home from my date with Dan.”
“How’d it go?”
“We had a nice dinner & ended up at the lake.”
“And…..”
“Well, I gave him 2 bjs & he ate me twice.”
“Way to go, Carly. Are you still a virgin?”
“Yeah, we didn’t go that far. I’m not ready.”
“That was still a big step.”
“It sure was. I swallowed it too.”
“I bet he loved that.”
“Oh yeah.”
“I told you it wasn’t that bad.”
“You were right.”
We sent a few more messages about other things and agreed to talk more at school in the morning.
Diane and I were talking by our lockers when we got to school. Apparently, Dan had already bragged to Mike about what great blow jobs I gave him the night before even though it was my first time. I could tell by the way Mike looked at me but I couldn’t be mad because I told Diane everything we did too. I had mixed feelings about someone else knowing what we had done together but I was also proud to know that Dan was serious when he told me how good I was.
When I saw Dan in the hallway a little while later, he told me what a good time he had the night before and we walked to class together. My pussy got wet just thinking about sucking Dan’s dick and swallowing his cum. I kept glancing over at him during class. If he noticed, I’d give him a little grin and go back to listening to the teacher. I was squeezing my thighs together to help relieve the itch that was growing between my legs. I was restless and I felt like I needed to touch myself to help scratch that itch but that was impossible.
I would squirm in my seat all morning thinking about being with such a cute guy like Dan. He was always part of the popular crowd because he was an athlete and handsome. I was now dating him but I wouldn’t exactly call him my boyfriend. It was still nice to be seen at school with him, Even if he wasn’t in my class, he would still walk me to my room and meet me afterward.
At lunch on Friday, Diane gave me a banana as a way to tease me about giving my first blow job the night before. She told me I was lucky that Dan ate my pussy too because some guys just want to get off and forget about the girl’s needs. I told her I thought I was ready for the next step but wanted it to happen someplace other than at the lake.
Later that day, Dan offered me a ride home from school and I invited him inside. My parents wouldn’t be home from work for another 90 minutes or so. They wouldn’t be pleased if they found a guy at the house when they got home and I made that clear to Dan. He understood. That didn’t stop him from asking me for another blow job though.
“If your parents aren’t going to be home for a little while yet, maybe we can, you know, have some fun.”
“What did you have in mind?” I asked but knowing what he’d probably say.
“How about another blow job? If you do me, I’ll do you.”
“Alright, but you have to go right after, okay.”
“Sure, no problem.”
I was so fucking horny all day, I was either going to have oral sex with him again or Jill off when I was alone. There is no doubt it would be better having him lick my pussy and I didn’t mind sucking his dick again. I was actually looking forward to it. We went into the family room in the back of the house just in case my parents came home early. We’d at least have time to cover up what we were doing.
We began to kiss on the sofa and Dan quickly had my shirt and bra off while I stroked his dick through his pants. After a couple of minutes, he pulled away and lowered his shorts and underwear indicating that he was ready for me to blow him. There was no hesitancy on my part as I lowered my head to lick his balls and shaft. I played with the head of his dick, licking and sucking it before taking him deep into my mouth.
“Oh baby, you give a great blow job.”
I was proud that I was a quick learner when it came to cocksucking. I was enjoying myself too knowing Dan liked my cocksucking abilities. I loved having his hard meat in my mouth while my lips and tongue worked him over. His soft moans of pleasure made me want to continue to please him. I was getting more comfortable with him seeing me partially naked and playing with my tits while I sucked him. I loved pleasuring him. The positive feedback made it more pleasurable for me too.
“Oh yeah, just like that. Oh, that feels so good. Oh fuck, you’re good at this.”
I could feel my pussy getting damp as I sucked his dick. I heard the familiar sounds of Dan’s breathing getting heavier with him grunting a little. When he grabbed the back of my head, I prepared myself to swallow another load of his cum. I felt his dick throb and pulsate in my mouth as he pushed himself in deeper. I almost gagged but fought it off. He then began to shoot his jizz into my mouth. I softly moaned and willingly sucked the tangy nectar from his erupting dick.
When he released his grip from my head, I knew he was done cumming. I sucked him a little bit more before lifting my head. I still had his dick in my hand and gave him a couple of more jerks which released a few more drops of cum. I leaned over and licked it off, not wanting to waste even a drop of his precious cum.
“Wow, you really like the taste of my cum don’t you, Carly?”
I shrugged my shoulders and replied, “It’s not bad.”
I didn’t wait for Dan to say anything as he pulled up his pants while I pulled off my panties and said, “My turn.”
“You earned it, babe.”
Dan dove between my legs. I didn’t feel embarrassed at all about exposing myself to him. He kissed and teased my thighs before licking my pussy lips and tongue fucking me. I softly rubbed the back of his head as I moaned in pleasure. His finger replaced his tongue inside my pussy so he could concentrate on my clit. His tongue felt so good rubbing up against my clit. I liked it even more when he began to suck on it and flick it with his tongue at the same time. He had me bucking wildly in a matter of seconds.
I lifted my hips as I began to cum. I felt my juices flowing out of my pussy. I was hoping Dan wasn’t turned off by that much cum but he never lifted his head. I came much harder than I did the night before. It took me a minute or two to regain my composure.
I then told Dan, “You better leave. My parents will be home in a little while.”
“No problem. I, uh, wanted to ask you if you wanted to hang out tomorrow night. My parents are going away for the night and won’t be home until Sunday. I thought we could get something to eat and then come back to my house to watch a movie or something.”
I knew exactly what that meant by “something” and I was ready for whatever might happen so I replied, “Yeah, that sounds like fun.”
“I could have my buddy get us some beer or something too. You know, have a little party.”
“What time do you want me there?”
“I don’t know, seven or so.”
“I’ll be there.”
“Great, I’ll see you then.”
We kissed some more and he groped my breasts and ass before he left. I was even more excited than when I was blowing him or when he was eating my pussy. I just arranged for a date to lose my virginity. I was so excited, I sent Diane a message.
“Dan just left my house and I blew him again. He did me too. He’s good at it. I’m going over to his house tomorrow night and his parents won’t be home.”
“Are you going to finally do it?”
“Yeah, probably.”
“We’ll have to go shopping tomorrow to make sure you have something special to wear.”
“I’m so excited.”
“I bet he is too.”
On Saturday, Diane and I went shopping early. I bought a sexy black lace bra with a matching thong to start with. Diane helped me pick out a low-cut darker blue cami crop top and a plaid pleated mini skirt. I planned to pair them with a pair of cute sandals. The top showed more cleavage than I usually do but it was going to be a special night.
Over lunch, Diane was telling me about when she lost her virginity and how it hurt a little until her hymen broke. It scared me a little but she told me it was nothing to be concerned about. She told me to make sure to text her afterward.
After we ate, we went to Dan’s baseball game and I was proud as ever when he came over to talk to us when he had a chance. Everyone saw him give me a quick kiss before he had to leave. I knew the other girls hanging around were jealous that Dan was with me. No one had ever been jealous of me before. I was on cloud nine. I spent the next couple of hours cheering on my guy, a guy that I was going to give my virginity to later that night. When the game was over, Dan came up to me and put his arm around me, and gave me a long kiss before he got on the team bus.
He told me, “I can’t wait for tonight.”
“I can’t either.”
Just before I dropped off Diane at her house, she told me, “Tell your parents you are sleeping at my house tonight.”
I naively asked, “Why?”
She shook her head in mock disbelief and replied, “You know, in case you want to spend the night at Dan’s.”
“Do you think he’d want me to?
“Hell yeah, especially if you guys want to fuck all night. If you want to leave you can still sleep over and tell me all about it.”
When I got home, I still had a couple of hours until I was going over to Dan’s house. I told my parents that I was going to spend the night at Diane’s just like we talked and they didn’t question it. I took an extra long shower and fixed up my hair just the way I like it. I was so nervous it took me longer than usual to put on my makeup.
Before I got dressed, I checked out my body in the mirror. Maybe, just maybe, I had a better body than I gave myself credit for. While my breasts weren’t as big as some girls they were still a decent size. I filled out my 34b bra and Dan seemed to like them. My legs were firm and my ass was bigger than I liked but I got a lot of compliments when I wore leggings. I made sure I trimmed my pubic hair too.
I checked myself when I put on my bra and thong and again when I was fully dressed. I looked good and felt sexy. Thank goodness my parents weren’t home when I left for Dan’s. I don’t like lying to them and my mom always seemed to instinctively know when I was up to something. I was nervously excited on the drive over there. I thought I was ready to lose my virginity but was afraid I was going to chicken out. I really liked Dan and if I was going to have sex for the first time, he seemed like the perfect guy to do it with. If it wasn’t him, I didn’t know who else it could be. It was now or wait weeks or months.
When Dan answered the door, he said, “Wow, you look great and sexy too.”
“Thank you. I hoped you’d like my outfit.”
“Like it? I love it.”
Dan gave me a big hug and kiss and invited me in while he got his car keys and wallet. He planned on taking me to an inexpensive Italian restaurant and then coming back to his house to watch a movie. I knew darn well we weren’t going to watch a movie or, at least, I hoped not. We were both horny eighteen-year-olds so the likelihood of us having an evening without some sort of sex was zero. When Dan said his parents were going to be gone for the night, we both knew what was going to happen if I went to his house. This was the perfect opportunity for both of us.
It’s amazing how much of a gentleman a guy is when you’re wearing a short skirt. When Dan opened the car door for me, I knew he was trying to look up my skirt. I made sure to part my legs a bit more than usual as I got into the front seat. I’m sure he got a look at my black thong but that’s what I was trying to do.
I was so excited about what this night was going to potentially mean for me that part of me wanted to skip dinner and go straight to Dan’s bedroom and have sex. I had anticipated this for so long and now that it was here. I was anxious to have the experience I’d dreamed of. However, I also dreamed of having a nice romantic evening so I knew I had to let this play out.
My desire for Dan only grew more intense throughout dinner and I was hoping he was feeling the same way. I’m not going to say I was in love with him after only dating him for a short time but I was very attracted to him on a spiritual and physical level.
After dinner, we left the restaurant and we both knew where this evening was headed. I’m sure Dan wasn’t 100% sure he was going to take my virginity after coming so close a couple of times and not doing it. There was no doubt he was going to at least try to fuck me. However, he knew he was going to at minimum get a blow job or two but in my mind, I was ready to take our relationship to the next level.
I was anxious on the ride back to Dan’s house. A person never forgets the guy or girl they were with when they lost their virginity. It’s a memory that will last a lifetime. I don’t know that I loved Dan but I liked him a lot. He was a nice guy, cute, and sexy. He was a two-sport athlete who was popular in school and I was proud to have him interested in me. He never referred to me as his girlfriend but after all that we had done together, I guess that was a foregone conclusion in my mind.
When we got back to his house, Dan fixed me a very strong rum and coke while he had a beer. I guess he wanted to make sure I was nice and relaxed for what he hoped was going to happen that evening. I never said I was going to have sex with him but there was no doubt he was going to try and fuck me. It was like we had a silent mutual understanding when I agreed to hang out with him while his parents were gone.
Dan turned on a movie, I don’t even know what it was because it didn’t matter. I cuddled up close to him and in a matter of minutes, we were making out on the sofa. We only broke our embrace to sip more of our drinks. I don’t drink very much and the alcohol went straight to my head and it only made me hornier than I already was but that was probably part of Dan’s plan for the night. His hand was up my skirt fingering me through my thong while the other was awkwardly fondling my breasts as we kissed. I naturally began to stroke him through his pants.
We were both breathing heavily and it was obvious that we were both ready for more when he asked me, “Do you want to go upstairs to my bedroom?”
I knew that meant, “Do you want to fuck?” and I replied, “Yes, I do.”
Dan quickly refilled our drinks and led me to his bedroom. I got more nervous with each step I took up the stairs. I was about to have full-blown sex with a guy. It was something girls talk about with their friends wondering what it would be like. I knew I was ready to take that step and I knew Dan was the guy I wanted to give one of my most precious gifts to.
I could tell he took a lot of time cleaning his room for that night. It was spotless. I doubted any teenager kept their room that clean all the time. Even though I was ready for this moment, I was still nervous and almost shaking. A girl only loses her virginity once in her life and it was about to happen to me. There was no going back now. Dan took me in his arms and we began to kiss again. He slid his hands up the back of my skirt to grasp my ass and pull me closer to him. I could feel his hard cock pressing against my thigh.
Dan took half a step away from me and began to pull my top over my head while telling me, “You’re a beautiful girl, Carly. I love that you’re so smart and sexy too.”
“I think you’re a great guy too, Dan. You are the sexiest guy in school.”
He then unzipped my skirt and let it fall to the floor. I was standing before him in my new black lace bra and matching thong. Dan then quickly stripped off his clothes as I stared at his erection. I had seen it before, held it in my hands, and sucked it but this was the first time I saw Dan completely nude. He was even sexier naked than I imagined. He had a trim muscular body with just a touch of hair on his chest and nice firm legs.
He unhooked my bra and tossed it aside. Dan immediately began to fondle my breasts and suck on my nipples. My pussy was dripping wet and I was so nervous, I fought to keep myself from shaking. As he was sucking my tits, Dan began to peel my thong from between my ass cheeks and exposed my pussy. He stopped playing with my tits while he stripped my thong down my legs. I stepped out of my thong and presented myself to him. Dan stepped back to gaze at my naked body. He had seen parts of my body before but I was never completely nude in front of him either. I blushed a little while feeling a little self-conscious. I hoped he liked what he saw.
He lightly ran his hands over my naked body while telling me, “Fuck, you’re gorgeous.”
Dan made me feel pretty and sexy and that’s why I wanted to fuck him. He guided me over to his bed as we got closer to that fateful moment. He laid down next to me as we began to make out again but this time, we were unencumbered by any clothing. When he slid his hand up my thigh, I instinctively spread my legs wider to give him full access to my pussy. We kissed as he fingered me as I stroked his dick. He began to kiss his way down my body, taking time to nibble on my neck and play with my breasts before positioning his head between my legs.
I liked the fact that Dan was taking his time and not just trying to stick his dick in me. I loved when he licked my pussy and appreciated that he was going to make sure I was ready before we did anything else.
I was so hot that night, it didn’t take long for him to bring me to orgasm. Not only did it help prep me for the next step but it helped relax me too. Don’t get me wrong, I was still nervous but I wanted to get fucked, I needed to get fuck by then.
When Dan got up from eating my pussy, his hard cock was pointing at me and I asked him, “Do you have a condom? I’m not on any birth control.”
“Yeah, sure. I’ll get one.”
He got a condom from his nightstand and I anxiously watched as he put it on. When Dan got between my legs, I was so nervous, I almost began to cry. I don’t think he even noticed. He was too focused on taking my virginity. Dan spread my legs a little further and I felt his cock pressing against my pussy. I braced myself for him to go further.
I felt him pressing against me but it wouldn’t go in at first. He gave a more forceful thrust and I felt his dick enter me. The first few thrusts were a little uncomfortable, but after that, it felt good and natural. I was scared but excited. I was super horny and I remember a hot quick sharp pain as he penetrated me and then some pressure as he slid himself deeper inside me. It was a little sore but a good sensation. Dan began to slowly move his hips back and forth and any discomfort slowly disappeared.
My first thought was, “This is it, I’m no longer a virgin.”
Dan began to kiss me as he fucked me. I felt a deep passion for him and his dick moved in and out of me. He moaned softly with each thrust of his dick. He was so cute and sexy and I just wanted to please him while I experienced the feeling of having a dick inside me for the very first time.
The longer Dan fucked me, the more I began to relax and enjoy the experience. I started to moan too as he thrust faster and faster in me. I looked up at his handsome face to see a look of pure rapture as he thrust himself into me. His face grimaced like he was in pain but it was, in fact, just the opposite. I was pleasing my guy in the most intimate way possible. My hands were holding his bare back as he thrust into me. His hot skin made me feel more horny myself.
Dan had a distinct moan the closer he got to orgasm I discovered while blowing him previously. When I heard that familiar rhythmic groaning, I knew he was close. He pushed himself deep inside my pussy and I felt his cock begin to pulsate as he began to cum.
Even though Dan was wearing a condom, I could still feel the force of his orgasm. He came for a while from deep inside his balls. He kept shooting his cum into me, being captured by his condom, until he collapsed on me. I wrapped my arms around his hot body, cherishing the fact that I was now a woman. I fucked a guy and he fucked me.
When Dan withdrew his dick from me, he said, “Wow, that was great.”
“I enjoyed it too, Dan. More than you’ll ever know.”
I’ve heard other girls say how it wasn’t that great to lose their virginity. Some girls said their partner came too soon or it hurt too much but I thought it was wonderful. Yes, I was nervous and it took me some time to relax and enjoy it but once I did, I liked having a dick in my pussy.
After Dan took off his condom in the bathroom we went downstairs to get more to drink and grab some snacks. He gave me his basketball jersey to wear while we relaxed.
While Dan was in the kitchen, I sent Diane a text message, “We did it.”
“How was it?” Diane asked.
“It was wonderful, better than I dreamed it would be. I’ll tell you more tomorrow.”
Dan caught me texting and asked, “Who are you texting?”
“Oh, just Diane. I told my parents I was staying at her house tonight.”
“You can stay here if you want. My parents won’t be home until tomorrow afternoon.”
“Are you sure, Dan?”
He grinned and replied, “Positive.”
I told Diane I’d be spending the night with Dan and she replied, “You go girl. Fuck his brains out.”
Dan and I had some snacks and another drink which wasn’t as strong as the others. I could feel his eyes looking at my partially clad body. Most of my legs were exposed and my breasts were hanging out of the top.
We began to kiss again and with a sheepish grin, he asked, “Do you want to go back upstairs?”
“Sure, let’s go.”
The second time was much better than the first. I was more relaxed and knew what to expect. We started with a sixty-nine which I loved. I had come to enjoy giving Dan a blow job and having a hard cock in my mouth. It was even better having him lick my pussy while sucking his cock too. It also gave me better access to lick and suck on his balls than being cramped in the backseat of his car.
After I came, Dan had me bend over so he could fuck me from behind. I felt more submissive being bent over for some reason. I liked sticking my ass in the air and offering him my pussy that way. I had to help guide his dick into me but once he started fucking me, I couldn’t help but push back against him to fuck him in return. I found I liked fucking doggie style.
The first time we fucked, Dan took his time and went easy but this time, he was fucking me so hard, his hips were slapping against my ass. I could feel my butt cheeks rippling with each thrust and he made me cry out in ecstasy.
“Oh fuck, that feels so good. Fuck me, Dan. Fuck me hard.”
This time felt so much better than the first. Now that I was no longer a virgin, I was able to relax and fully enjoy the feeling of being penetrated by a nice hard cock. It also made it better for Dan.
“Oh yeah, that’s it, baby, take my dick. Oh, your pussy feels so good, so tight.”
Dan had his fingers embedded in my butt cheeks as he pounded my pussy. He was able to last a lot longer this time too after cumming earlier. He was fucking me so hard that he began to tire and slowed down to catch his breath.
“Do you want to get on top?”
“Yeah, sure.”
We switched positions and I slid down on Dan’s dick. I liked being able to control the pace and the positioning of his dick inside me. My tits were flopping around as I fucked Dan. He played with them too as I rode him. I would even lean down so he could suck on my tits as our hips moved in unison to fuck one another. Now I knew why the other girls enjoyed having sex so much.
When I began to tire, Dan laid me back with my legs on his shoulders and gave my pussy a good hard pounding. I was moaning and writhing underneath him while begging for more. I had my first vaginal orgasm while Dan was fucking me in this position. That triggered his orgasm too.
After he came, my first thought was, “I have to get on some type of birth control so I can feel his cum inside me.”
Dan and I fucked again that night before we fell asleep in each other’s arms. In the morning, Dan woke up first. I could feel the movement in the bed and around the room so I woke up too. He said he was going to fix breakfast and I said I’d join him after my shower. While the hot water cascaded over my naked body, images of seeing Dan’s face while fucking me ran through my mind. I thought about the feeling of having his hard cock plunging in and out of my pussy. My hand drifted down between my legs as I began to tickle my clit. My pussy was hot again but I didn’t want to come right out and ask Dan to fuck me again. As I was drying myself off, I decided to put on his basketball jersey again and see what would happen.
His jersey was a glorified, oversized tank top that came down to just below my ass. It showed off plenty of side boob that I hoped he would notice. When I got to the kitchen, Dan was busy making bacon, eggs, and toast. He looked so sexy standing there in the tight boxer-jock underwear. It highlighted his cute tight ass and got my juices flowing even more.
Dan stopped cooking long enough to tell me, “You look sexy in my jersey.”
“You look pretty good in your underwear too.”
Dan kept sneaking peaks of me as I got some plates out of the top shelf of the cupboard. I had to reach up high to get them and I could feel the cool morning air against the bare skin of my ass so I knew he could see my butt cheeks. I pretended to struggle to get plates so I could moon him a little longer. I did the same thing while bending over to get the orange juice out of the fridge.
There was a noticeable bulge in Dan’s underwear as he was putting the food on our plates. We talked about the night before as we ate our breakfast. I told him it was much better than I expected and what a great time I had. He told me he had fun too and how lucky he was to have such a beautiful sexy girlfriend. My heart fluttered because that was the first time he referred to me as his girlfriend. I was even happier that he was the guy that took my virginity and now he was my first serious boyfriend. When we were done with breakfast, he leaned over the table to kiss me.
While I was washing the breakfast plates, Dan came up behind me at the sink and began to kiss my neck and fondle my breasts underneath the jersey. I could feel his hard-on pressing against my ass. When I turned around we began to kiss deeply. I told him we should finish cleaning up the kitchen first which he reluctantly agreed to.
As I was wiping down the kitchen table, I made sure to bend over to show off my ass and pussy again. I guess Dan couldn’t take it anymore as I felt him approach me and rub his dick in between my ass cheeks. I stood up as he pulled the jersey off my body and grasped my tits again. Dan pushed me face down onto the table as he pulled his underwear down and slipped his dick into me. He began to fuck me right there on the kitchen table.
I began to cry out, “Fuck me, Dan. Your dick feels so good. I love how you fuck me.”
“I love your pussy too. Damn, you’re so wet and horny.”
“I sure am horny. I can’t get enough of your cock.”
“Well, you know where to find my dick any time you want it, Carly.”
“Ohhh, you know where to find my pussy any time you want it too.”
Dan drilled my pussy hard. I was so fucking horny, it felt good to get fucked again right there in his kitchen. I then realized we didn’t have a condom.
“Don’t cum in my pussy. I don’t have any protection.”
“Okay, you can suck me when I’m ready to cum.”
Dan was giving my pussy a good pounding and I was loving it. I could tell when Dan’s orgasm was approaching and got concerned.
He then told me, “I’m about to cum. Get on your knees.”
When he pulled out, I immediately knelt before him as he stuffed his dick in my mouth. He held my head still as he face fucked me. I devoured his dick wanting to taste his cum again. Pleasing Dan was the only thing I wanted at that moment. He stopped his thrusts for a quick second then lunged deep into my throat and began to shoot his tasty cum into my mouth. I eagerly swallowed every last drop. I wanted to keep sucking his dick but unfortunately, he went limp in my mouth.
Dan had me sit on the table and spread my legs while he licked my pussy to another orgasm. After we recovered, I got dressed and went home but not before Dan and I agreed to hang out again later that night. I called Diane on my way home and told her every last detail about the night before and that morning.
She told me, “You fucked him FOUR times? You little slut.”
“That’s right and we’re getting together tonight too.”
We decided to get together for lunch. Diane was so happy for me and I was happy for myself. I lost my virginity to my new boyfriend who was a hot, popular athlete.
Like most young couples that discover great sex, we took every opportunity to get together and fuck. We did it in the back seat of his car up at the lake; we did it after school at my house before my parents got home or at his house whenever his parents went out. We snuck off at a party and fucked in one of the bedrooms, on prom and graduation night. When I had my period I sucked his dick.
Nothing lasts forever as Dan and I were going to different colleges in the late summer. I wanted to try a long-distance relationship but Dan wasn’t interested. Even though I was brokenhearted, I knew he was right. That didn’t make it any easier though. He will always be my first love and the guy that took my virginity and I will remember him and that night for the rest of my life.