At the end of 2015 I was 25 years old and I had never had an orgasm. I had only kissed two guys and fooled around with one. I never even thought about trying to masturbate. I was taught my whole life that any sexual pleasure of any kind outside of marriage was a mortal sin, and for the first quarter century of my life I completely believed it. When I was 19 I'd dry hump my first boyfriend, both of us naked from the waist up, him in his jeans and me in yoga pants or leggings, and he'd be sucking my nipples, I'd get unbelievably wet and would feel pressure building inside, and it would scare me and I'd ask him to stop. He always would but I knew I frustrated him alot and I feel really guilty for that now. But at the time I was bound to my principles. Even when I moved three hours away from my family for college and then for work, I was never tempted to explore or experiment at all.
Then I agreed to do a play for my friend and met a guy in the cast. We started talking, became friends, and eventually one night at karaoke we kissed. I started falling for him hard and fast. What attracted me to him the most was he knew how inexperienced I was and had absolutely no intention of pushing me, anything we did would be my call, like he had no intention of even suggesting anything.
He took me on a road trip to see a production of Next To Normal and after the show we ended up on a backroad making out in his backseat, we had our shirts and shoes off, he'd taken his socks off, I took my bra off and he was sucking my nipples while dryhumping me (both of us wearing jeans), which was how far he knew I'd been with one guy prior, and it felt sooo good, feeling his bodyweight on me, our tongues in each other's mouths, his bare chest pressed against my bare breasts, my nipples in his mouth, my bare feet touching his bare feet (a sensation I'd grow to really love as he had a thing for feet). My breathing was starting to get shallow and ragged and again that familiar pressure was starting to build and I got scared and asked him to stop.
He stopped, no questions asked, we got dressed, and he drove me home, not talking about it again for a few weeks. Then one night we were at my place after dinner watching a movie, his toes are brushing my bare feet making me excited, we start making out, and to my own surprise I said I wanted to hump again. He took off his shirt, I pulled down my dress past my boobs and hiked it up, so this time instead of humping me in jeans he's doing it against my panties, and we're making out and and he's sucking my nipples, and again my breathing is starting to get shallow and ragged and there's that feeling again and again I tell him to stop.
This time though we started to have a conversation about it. I tell him I want to have an orgasm but I'm scared of losing control of myself and just letting him take my virginity. He tells me he'd never do that without having a deep conversation with me first. So I let him start humping me again and pretty soon I let myself go over the edge. At 25 years old I experienced my first orgasm.
After I calmed down, I pulled my dress up over my boobs and left him on the couch to go change my underwear. I came back and I don't really know how to feel. He asks me if I have any regrets and I honestly said no. That didn't mean regrets wouldn't come later but at that moment I was honest when I said no. He told me if we'd have kept going a little longer he would have finished too and I offered to let him hump til he came but he wasn't in the mood to drive all the way home with messed up underwear. So I said he could go into the bathroom and finish up. (Yes I was aware of what masturbation was, I wasn't a total idiot).
About a minute after he left for the bathroom, I had a bold idea and before my brain could stop me my bare feet led me from the couch to the bathroom. There he was, his shirt still off, stroking his dick over my toilet. He jumped when he noticed me come in and tried to put it away but I told him I wanted to watch, I let my dress fall to the floor leaving me in only my panties, stood next to him, and I let him play with my breasts as he stroked. Seeing a penis for the first time was...well I don't know what I was expecting to feel but I felt so naughty in a good way. He leaned in and kissed me and then made himself cum into my toilet. I wish I could tell you how it felt seeing a guy orgasm for the first time but I honestly don't remember, I felt overwhelmed at that point, but not in a bad way.
A few nights later we're at my place again, we go to my bedroom this time, we're both barefoot and naked from the waist up, he's in his jeans, I'm in my leggings, we lay down and start humping but something feels off, I'm not feeling the pleasure I usually feel. He suggests we lose our pants and I agreed. He took his jeans off and then he helped me get my leggings off. As they passed over my feet he asked if he could suck my toes. I, being very intrigued, said yes, and holy shit it felt so good. Then he climbs on top of me and starts humping me, we're stripped down to only his underwear and my panties, it's feeling so good, we're kissing, he's sucking my nipples, and his dick comes out of his underwear, I guess it worked its way out the top as he was humping. He apologizes and goes to put it back in but I tell him not to so he starts humping me using his bare dick. I was feeling on fire, I pulled his underwear down further and started grabbing his bare ass. I came for the second time in my life and I told him I wanted him to keep going until he came too. He warned me it'd go on my bare stomach but I wanted it so he just let it happen. I felt his warm cum shoot onto my stomach. And then we just laid there making out and cuddling before he got a washcloth and cleaned me off.
That night I thought I was okay with it. But the next morning I woke up with this overwhelming feeling of guilt, like there was a little man with a megaphone running around in my head telling me how I need to stop this sinful behavior immediately or I'd go to hell. I texted him that I didn't want to hump anymore. I know he was disappointed but he didn't argue at all.
So a few weeks go by and we'd been going on dates and making out and he'd been rubbing my feet but neither of us even tried to bring up our adventures together. But then a few weeks later I was laying in bed wide awake and felt SOOO horny. I was wetter than I'd ever been in my life. I wanted to hump him again so bad. I took my tank top and pajama pants off, leaving me in just my panties, and started humping a pillow. I started touching my bare breasts, remembering how good his hand and mouth felt on them. Eventually I decided, what the hell, and took my panties off and started humping my pillow totally naked. Before too long I exploded in the third orgasm of my life and my first ever self-inflicted one. At 25 years old. (If you think that's pathetic, there's more pathetic stuff later but I'm getting ahead of myself).
In that moment, I was so excited. I texted him that I'd gotten myself off for the first time. The next night we went out to dinner and then went back to my place, went to my bedroom, kissing while undressing each other until he was in his underwear and I in my panties. We lay down under the covers for the first time, he started kissing down to my nipples and I suddenly had an idea. I asked him to go check that my front door was locked. While he checked, I quickly slid my panties down and off. He came back to bed, resumed kissing my breasts, and it took him a little longer than I would have thought to realize I was totally naked but as soon as he did, he was ecstatic. He asked permission to take his underwear off, I said yes, and OMG feeling his naked body on mine as we made out was absolute heaven.
Most (not all) my inhibitions were obliterated in that moment. I finally got the nerve to suck his nipples, which he'd said felt really good but I'd been hesitant to try, that's since become standard foreplay for me. I let him suck my toes again and lick my feet this time. I let him touch and grab my bare ass. And then I said I wanted to show him how I'd masturbated. So I grabbed my pillow and started humping it. Seeing him laying there totally naked stroking his cock as he watched me hump my pillow totally naked was amazing. I made myself cum, and then he made himself cum on his stomach and chest. I told him not to clean himself up and pressed my naked body against his, feeling his cum on my skin as we kissed. We kissed and kissed for a long time. I could feel his cock getting hard again against me. He asked me if he could try something, he told me to turn on my side with my back to him. He started kissing my neck while gently touching my breasts, stroking my nipples, and then he slowly started to touch my clit. I was in heaven. Long story short, he soon rubbed me to orgasm. After that I turned around and without even asking, grabbed his dick and started stroking while sucking his nipples. When he said he was going to cum I let him cum on my stomach and boobs, which again I decided "What the hell?" and tasted some of it. It didn't taste nearly as bad as I was expecting (you'd be amazed the ideas a religious, sex-negative upbringing can put in your head.)
A few nights later, I tried masturbating again, but this time looking at porn. I laid in bed totally naked watching a variety of videos, mostly amateur couples. I tried fingering myself this time and I loved it even more than humping. I made myself cum twice and even squirted a little. I also made sure to watch a few blowjob videos just in case...Our next date we got naked again, and this time we did oral for the first time. OMG the first time he ate my pussy, it was the best feeling in the world. Compared to other guys (and one girl) I've been with since then, he's still the best oral I've ever gotten. And then I gave him my very first blowjob. I really enjoyed feeling him cum in my mouth.
This continued for about a month or so, we'd get naked and get each other off but never going all the way...until my contract at work was almost up and I was about to move back home. I tell him I want to lose my virginity to him. He kept asking to make sure that's what I really want. I said as nervous as I was I knew I'd regret it more if I didn't...
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