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(For clarification. All events in this story occurred when both parties were 18 years old).
My first real boyfriend was Kevin. He was on swim team and had the kind of body I like– thin and strong but not bulky. He had strong Germanic features, curly dark blond hair. He treated me well, too, never cheated and always showed caring about me and my feelings. I think it was because he was head over heels in love with me.
He was the guy I lost my virginity to and we fucked occasionally as we had a chance, but as teens living at home it was always difficult to find a time and place and situation where we could go all the way. We’d do it in his car every once in a while, and he sort of kept his eye out for other places or situations where he could get under my clothes or in my pants.
The first time I’d actually let him inside and he’d cum, there was no condom. Hey, we were teens in the middle of lust (I remember I was seeing red I was so horny and didn’t even think about consequences). Later I insisted he get condoms, and he had some but sometimes we found ourselves in places where we hadn’t predicted we would need it and he didn’t have one with him. A couple of times we did it without a condom and he pulled out before he came. The perfect scenario of teen pregnancy. I didn’t realize how lucky I was.
The usual way of handling a guy who wanted sex but didn’t have a condom was a hand job, then later I graduated to blow jobs but really didn’t like those that much and really would just use my mouth to supplement the hand job if I had to.
It was always sort of a compromise, those situations. I’d be aroused, wet, loving the feel of his hardness on my thigh or my pussy through his pants, kissing him, letting our hands roam. Sometimes getting to dry humping through jeans. But then the guy would want to get inside and I would be like… nope. I wasn’t that good at keeping my guard up, but I did try… at least halfheartedly.
“But Polly, fuck, I am so horny. And you have got me nearly there.”
“No, Kevin (or George or Jason or whomever), I am not gonna get pregnant. No way.”
“But I will pull out before I cum. Honest.”
Right about then I’d give in, grab his cock with my hand and his whining would morph into moans.
Honestly, with some guys I did this just to get them off my back. But with Kevin, I would have preferred to actually spread my legs and do it. He was my boyfriend, and I loved the feeling of him penetrating me. I liked the feeling of how hard he was, and how my body made his body simply lose control. I liked feeling his weight on me after he came, being able to put my arms around him and hold him. I also admit I really, really liked orgasms, which I didn’t get giving hand or blow jobs.
Well, Kevin and I had begun to do it a bit more regularly, because he was my boyfriend after all and we’d find situations to make out. At the beach, in the Jacuzzi, heck, we made out in the back of a church once. Or twice. He really wanted to get inside that time, get his cock into my pussy and I was like, not here, and you don’t have a condom! You’d think he would be able to keep condoms around, but I think he was afraid his parents would see it in his wallet or something, so he only brought one when he thought we were actually going to get naked. Which wasn’t often at all.
Well, after like the third time I’d told him no, he couldn’t enter me without a condom on and jacked him off instead, he asked if we could try anal.
“What? Um….” I knew what anal was. It was actually famous for being the way to fuck without getting pregnant. Safe sex. (It wasn’t safe disease wise, of course, but I wasn’t nearly as concerned about that back then). It also was famous for being weird, perverted, kinky and unpleasant. I had a girlfriend who had confessed to trying anal once and she told me it hurt like hell and the guy gave up after a while. So I was skeptical, even a bit afraid and rather grossed out.
But almanbahis şikayet it came up again. “Just let me put it in your ass, OK?”
“Grooossss….” was my response. We were in his car and he wanted me to roll over, push my ass up and let him penetrate from behind. I shuddered. “No… no… gross. No…”
This was my response, in general, when he’d brought up the concept of anal. No… gross…
It finally happened one evening when my parents were out to some event, I forget what but it was in LA and they’d be gone several hours. Kevin and I made plans for him to come over and watch a movie, which meant we’d watch three minutes of it, start making out, then move to my bedroom. That was pretty much assumed and I actually was feeling excited about having time to actually get fully naked with him and take our time. That didn’t happen often. In fact, being fully naked with him had maybe happened twice before.
It went down as expected except we didn’t even put the movie in to watch it, we just sort of headed to the bedroom. He had several condoms this time and we were ready to rock. We started making out as soon as we were in my room and the clothes were coming off fast. His cock was hard and literally bounced out of his pants. (Back then I think I was under the impression guy’s cocks were always hard because that’s the way they always were when I saw them). I grabbed it as we sank down onto the bed.
Skipping the non-relevant make-out details which involved pre-cum, some mutual body exploration of the detailed kind not normally possible while partially clothed, fingers probing, legs wrapping, tongues going places, etc.
He entered me in our usual position, the missionary, which was not only my favorite but also the only one I thought made any sense. (It remains my favorite position, actually). My legs were spread with knees bent and he’d just been thrusting a bit when he said, “Roll over.”
Well that was different, but we were in a rare situation here– in bed, completely naked with several hours to ourselves, this meant we could actually try being a bit more sexually adventurous, you know? That was what this was all about. Being able to do things without leaving our clothes on and making our sexual intercourse positions conform to the shape of a car.
He pulled out and edged back on his knees. I pulled one leg up, rolled over and spread my legs on either side of his, laying on my stomach. We’d done this a couple of times at the beach, so it wasn’t completely new.
“Up on your knees.”
Well, that was new. I’d not done that before. I knew what he was going for was called “doggie”. OK.
I could immediately tell this was an interestingly different position. With my shoulders and head down on the bed, my ass stuck way up and presented to him, it felt… awkward in a way. Like I was presenting myself to him more completely and openly than I ever had. It felt more exposed, the first time I had intentionally presented my ass and exposed my anus specifically, to a guy (or anyone). It was actually a bit embarrassing and I remember burying my head in a pillow right then. I could feel my ass cheeks spread slightly and the cooler air on my anus, which made it very obvious that I was exposed.
I hoped I looked good. Stupid thought, how many assholes look good, you know? And yet, I was thinking about that, wondering if he was thinking damn she got an ugly asshole.
So I was on my knees, ass up, shoulders and head down on a pillow on my bed and I could feel him move in, the bed shifted and bounced a bit as he got closer.
First, he put his cock in my pussy. Pushing gently, nicely (he was usually a considerate lover, at least as much as an experienced boy could be). It felt nice for him to enter my pussy and this was a position we hadn’t tried yet. We’d done it before on my stomach with him laying on my back (at the beach) but not with my ass up and him kneeling behind almanbahis canlı casino me true doggie style.
He reached up to my breasts and held them while he thrust a few times. It felt good to have him inside and I stopped worrying about my ass temporarily. I liked that he could grab my breasts while he was thrusting into me and my body was shoving up and down as he fucked me.
He then backed out and rubbed his condom covered cock over my ass. My mind suddenly refocused on the fact my anus was there, cheeks spread and completely exposed to him.
I was also thinking, that doesn’t feel too bad, having his cock against my anus. Sort of fun, different.
He moved it around my ass, pushing gently against my anus for almost a minute. I remember clearly feeling my sphincter contracting and relaxing as he did and I wonder to this day if he was sort of timing his first push for a moment when I was relaxed. I was damned horny right then, in the middle of fucking and when I am that horny and aroused I tend to be willing to do stuff I would say no to otherwise. So I didn’t stop him. His cock felt good against my anus.
He pushed a little, not much.
He hadn’t asked permission to fuck my ass, but he was giving me plenty of opportunity to say no. And I wasn’t. I was holding my position, ass up, cheeks spread, anus available to him. Because I was horny as hell and wanted him inside whatever way he wanted.
One hand reached down to my incredibly wet pussy and massaged, a finger going in. That made me moan and I worried less about the pressure against my anus. In fact, I didn’t care any more. If I had been able to think at that point, I would have thought “ewwww gross….” but I wasn’t thinking, I just wanted this boy to fuck me.
He pushed harder. My anus automatically contracted and resisted the penetration. He continued to rub his cock over my anus, occasionally pushing, probing, making a little headway only to be pushed back out again.
“Relax,” he said.
“I’m trying…” I said. Neither of us knew about the technique of pushing out like I was pooping, which makes the sphincter relax and open. He knew more about anal because he watched porn, but in those vids the girls always had gaping asses and could take huge cocks with no problem.
He kept pushing, and I kept trying to let him in. It didn’t hurt that much, it was just a bit frustrating. When he’d push a little more insistently I would let out a “ahh.. ahhhhhh.. uhhh….. oh god…” but that was it. His continuing to finger fuck me helped, it kept me aroused and interested and willing to try to do something kinky, which was most of the reason I was letting him do this. I wanted to do something perverted and this was it.
He suddenly pushed hard and got inside my sphincter, but not far. I think he got his head in, and that was about it, but it really helped. Once something was inside, he began a steady, very gentle back and forth motion. My anus sphincter was contracting and relaxing in convulsions around his cock (which was making him moaning, or grunt, or something, I think it felt good to him). Whenever he’d push when my sphincter had relaxed he got in a few more millimeters.
The sensation of having something inserted and expanding my anus wider was weird. Not unpleasant, but it felt a bit like I had tried to poop and it was stuck and then going back in the wrong way. But it didn’t feel bad and he kept rubbing my pussy and I pushed back against him a little, encouraging him.
After a minute or two he was in far enough that two things happened. First, I think my ass got used to having him there and stopped fighting it as much. I relaxed a lot more and he got in further. Second, he was in far enough to begin some real back and forth thrusting.
It didn’t really hurt, like, not pain. It was uncomfortable in a way, especially when he tried to shove in further. It felt unnatural, actually, more than painful per almanbahis casino se. But it was that unnatural feel that actually sort of excited me. Something going in my ass instead of coming out. And something unyielding, demanding, and larger. Stretching me.
I am bisexual, and enjoy sex with men and women (I prefer women but I have enjoyed many men), and one of the things I enjoy about guysex is the feeling of being penetrated. That feeling was much more significant in my rectum. I felt stretched, filled, and it was a struggle letting Kevin in, and that not only was uncomfortable, but excited me.
As he began pushing in and out more regularly he stopped rubbing my pussy, putting his hands on my hips. I was grunting (very unladylike) and moaned a bit but wanted him to keep stimulating me. Anal was not going to be enough to get me off. So I reached back, grabbed his hand and put it back on my clit.
He obliged and for the rest of the experience he continued rubbing my clit with one finger inside.
He came fast. Once he was inside and really thrusting, I think it took about a minute for him to do one final thrust. I could literally feel his cock pulsing in my anus as he ejaculated, which was sort of a new thing to me. I remember afterward going through the whole thing in my head and thinking about just how slutty I had become, how adult and experienced I was, to have felt a man’s cock inside my ass, pulsing as it ejaculated semen.
Kevin pulled out slowly and sat back on his haunches. I carefully rolled over onto my back. My ass felt a bit sore, but not bad. The whole experience had been uncomfortable, but also arousing and fun, and wasn’t nearly as painful as I’d heard. It was a bit of a struggle, yes. At times painful. But I discovered the excitement and arousal of letting my boyfriend penetrate me there and cum inside my ass… it was exciting and arousing enough that I was OK with it.
“How was it?” I asked as I lay there, my finger on my clit, rubbing it slowly.
“Fuck… it was good. Tight, really tight. I came so hard. Baby… you are so beautiful. I love you so much.”
He moved forward and lay on top of me and kissed me. I wrapped my arms and legs around him, holding him tight.
The next time we attempted anal was almost three months later. He asked a couple of times when we were at the beach or in the car and he had ‘forgotten’ his condom, but I said no. It was too difficult, I didn’t want to have to go through that in some cramped or risky semi-public space.
When we finally did try again we actually had a harder time getting it, partly because he wasn’t using a condom (what do we need that for, you can’t get pregnant there…). That’s when I got up and padded over to my mom’s bathroom and got some baby oil she kept there.
“Here. Use this,” I said. I’d heard of lube, but never seen any or actually used any. But it worked. That baby oil made all the difference in the world. I relaxed a bit, he pushed, and his cock just slipped in. It also made a huge difference in the actual fuck. The first time, my sphincter had grabbed his cock and when he pushed in and out the motion through my anus was minimal. My anus got pushed in and pulled out, though his cock inside rubbed the walls of my rectum. He also only got maybe halfway in, which was plenty to get him to cum.
This time he actually fucked me in the ass, sliding his cock all the way in deep, making me feel like I was totally filled, and then slid almost all the way out. My sphincter relaxed, and we fucked. And he came, leaving a load inside my ass for my first ever anal creampie, something I knew nothing about at the time, though I did quickly learn how to handle that. I leaked semen out of my ass for a bit before realizing I needed to go expel it and wipe up a bit… Ah… the things we learn when first starting out.
I needed to wipe anyway, my ass was full of baby oil.
Kevin and I were together a little more than a year, though I did cheat on him some. Anal was something I did only with him though until maybe a year after my breakup with him. After that, it became a routine part of any long term relationship with a male and it got a lot easier with time and experience.
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