A Summer Night Making Up for Lost Time [MF] [Str8]

Dorothy was a spectacular woman I dated for a few months during the summer between my junior and senior years of college. Although we only dated for a few months, we’d known each other for several years and I’d had a crush on her for some time, so I was excited to see if we could be something more than friends.

Dorothy and I met up for coffee one evening that summer at a place near her apartment. We’d been seeing each other for a few weeks, and I was generally really enjoying our dates. I’d just broken up with a mutual friend a few weeks before Dorothy and I started going out; that fact wasn’t strange for me, but I sensed it was a bit for Dorothy.

In any event, we met for coffee that night, and we got on the topic of sex. She very casually commented that she’d been told by previous partners that she was really good at giving head; I replied that I’d been told the same of my own skills. I liked where this was going, but at the same time I couldn’t believe my own good fortune.

Dorothy was very attractive in a very specific way. She was full-figured without being overweight, and dressed in a manner which was both conservative and alluring; for example, that evening she wore a long, black dress with a neckline which plunged just low enough to reveal a healthy hint of her full cleavage. Her long brown hair was parted down the middle, and was combed so it fell just a bit over her chest (just grazing the tops of her breasts).

After we finished our coffee, Dorothy invited me back to her place to jam a bit; since we were both musicians, we spent a fair amount of our time together at one of our places passing a guitar back and forth and singing songs. I can honestly say that singing with (or listening to) Dorothy was an arousing experience in itself: she had an amazingly emotive and sexy voice.

Back at her place, Dorothy kicked off her sandals and told me to have a seat. While she disappeared into the kitchen to grab us some beers, I noticed her guitar propped against the couch; I sat down on the floor next to it, grabbed it, and started to noodle around.

Dorothy returned from the kitchen and smiled incredulously, presumably due to my choice to not sit on any furniture. My decision wasn’t random, though; I had it in my mind that the floor would provide us the best access to one another, should something physical happen.

Dorothy joined me on the floor and we ran through one of the songs we both knew and loved by heart. After we finished, we each took a large swig of our beers, and I decided that was the moment I was going to put how I was feeling on the line: I told her that I really enjoyed spending time with her, and although it didn’t really matter now, I regretted that I hadn’t told her sooner how I felt about her deep down for some time. I wanted to at least try to make up for lost time, if she was interested in trying as well.

Dorothy smiled and looked down, her eyes no longer able to meet mine. I thought for a moment I’d blown it, but even so, I was glad I finally said what I had to. When Dorothy looked up, she was still smiling, and I suddenly felt like we may be okay.

Dorothy slowly moved closer to me on the floor. We sat for a moment just sort of looking at each other, and then Dorothy leaned over and kissed me. “We can at least try,” she said quietly, her eyes now again locked with mine, before leaning in to kiss me again.

I pulled Dorothy closer to me as our rather demure kissing turned into something much more. Especially amazing was how careful we were both being; it seemed like what we were both experiencing was more than mere lust, and we each wanted to ensure that the other person knew that. Ironically, that of course made everything that much hotter.

As we continued to make out, Dorothy moved from sitting on the floor in front of me to kneeling and leaning into me, her hands resting on my thighs. From that angle, I was able to see down her dress, and the fullness of her breasts pressing against the fabric—in tandem with her hands on my thighs—caused my dick to begin to harden.

For some reason, my arousal in that moment embarrassed me; here I had a beautiful woman kissing me and touching me in a sensitive place, yet I wondered if my natural reaction was inappropriate. Since there was nothing I could do about it, I quickly pushed those thoughts away, replacing them with my hope that—just maybe—I would get to experience those skills she’d told me much about.

I brought my hands up to Dorothy‘s shoulders, held them there for a moment, then used them to draw her a bit closer to me. Soon, Dorothy was basically sitting in my lap. Quickly, something primal in us both began to take over; as she broke off a kiss, Dorothy asked, “want to see my bedroom?”

I really, really did.

Dorothy stood up, and in helping me up took my hand and led me down a short hallway to her bedroom. She clicked the light on, and I saw before me about what you’d expect: a bed, a desk, and a bunch of general shit. However, it strangely fit the mood perfectly; her bed somehow looked amazingly lush and soft, and the whole room smelled of the same lotion as her.

I took a seat on the bed (because why not?), and Dorothy walked over to a small stereo on a bookshelf and put on some low music. After that, she turned around and walked over to the bed, taking a seat next to me. For a moment, neither of us said anything; we just sort of looked at each other with goofy expressions on our faces. We then both leaned forward and started making out again. I took the opportunity to begin running my hands up and down Dorothy‘s sides, including lightly feeling the sides of her breasts. Dorothy was focusing her hands near my face, which wasn’t an issue at all; her general sexiness made everything seemed erotic.

As our making out intensified, I began to lean back on the bed to see if Dorothy would follow; I was happy when she took the hint, leaning her body on top of me as I laid back. Soon, Dorothy was all but laying on topic of me, and my dick was getting progressively harder. Dorothy then sat up, and gestured for me to move over a bit; as I did, Dorothy filled the empty space as we then laid side-by-side. In this position, we had even more access to each other (I wished I’d thought of it!), and our hands began to explore each other’s bodies.

I was openly (but still tentatively) caressing Dorothy’s breasts at this point, their fullness and weight further increasing the stiffness in my pants. Although she was wearing a bra, I could feel her nipples begin to respond to my touch. Encouraged, I slowly started to kiss down Dorothy’s neck, which I was happy to find she was very into: she began to quietly moan as I made my way toward her chest.

As I reached Dorothy’s chest—kissing the area above her breasts, barely exposed by her dress’ neckline—Dorothy’s moans began to get louder. As she adjusted herself on the bed to give me better access, I noticed just under her dress the hint of a blue, silky bra. For the first time that evening, the thought of what Dorothy would look like out of that dress—and the thought that I might actually get to find out—shot my dick up to full attention.

Dorothy pulled my lips back up to hers, darting her tounge in and out of my mouth and softly sucking on my lips. After a few moments of that, Dorothy stood up and—without breaking eye contact—pulled off dress, placing it on a nearby chair. She stood there next to the bed in nothing but her blue, silky bra and black cotton panties, her hair again drapped over her shoulders and her manicured feet completing the sight; it was indeed a sight I took the time to enjoy.

“Are you okay with this?” Dorothy asked as she moved back toward the bed with a sly grin. I couldn’t even speak to answer; luckily the raging hardness of my dick was all the answer she needed. Joining me back on her bed, Dorothy straddled me and began to playfully tug on my shirt; I didn’t needed to be asked twice as I took it off and tossed it to the floor. Dorothy then leaned down and kissed me hard, moving one hand down to my jeans as she did.

There was no hiding my raging hard cock at this point, nor was there any need as Dorothy began to rub my dick through my pants. She then brought her hand back up, and—as she continued to kiss me and caress my face—began to grind her cotton-covered slit against my dick. Reflexively, I began to thrust my dick slowly to meet her grinding, now taking both of my hands and placing them on the sides of her breasts. As I worked my hands to the middle of each one, I discovered her nipples were rock hard; I couldn’t help the urge to tease each with my thumbs.

Dorothy let out a sweet but sexy moan as I played with her nipples, and she then broke off our kiss; “Just take it off,” she said with a little laugh, referring to her bra. Before I could do anything, though, Dorothy sat up and unclasped her bra herself, letting it slowly fall away from her tits before tossing it aside. Keeping in mind that Dorothy was still straddling (and slowly grinding against) my cock as she revealed her gorgeous and very round breasts, I’m lucky I didn’t cum right then.

Dorothy laid back down on top of me, her now naked chest pressed hard against mine as we sucked and licked each other’s mouths. I couldn’t help but gradually increase my thrusting against her, moaning as I did. Dorothy met my moan with a long one of her own, then she sat back up. She rolled off of me back onto the bed, and I wasted no time turning to face her; I wasn’t going to miss my chance to get her lovely tits in my mouth.

Dorothy‘s breasts were incredibly soft and full, her nipples almost too hard to believe in contrast. I licked and sucked each in turn, and Dorothy started moaning louder. As I began to kiss and explore the slight space between her tits, I felt Dorothy reach back down to my pants and start to fumble with my belt and fly. I was all too happy to take a moment to help her; Dorothy got my pants open, and I helped her take them off completely.

Dorothy surprised me by following my pants toward the end of the bed, readjusting herself between my legs as she did. In what felt like slow-motion, Dorothy pulled down on my underwear, freeing my hard dick at last. After a glance up at me to gain silent permission (which I wordlessly gave), she pulled my underwear the rest of the way down, tossing them too to the floor.

My incredibly hard cock now on full display, Dorothy shot me a knowing look before grabbing my dick at the base with one hand. Slowly, Dorothy massaged my shaft before finally lowering her mouth onto me. I involuntary threw my head back as I started seeing stars; Dorothy‘s lips on my dick felt spectacular. I didn’t even have time in the moment to consider how much I’d spent the evening wanting—just maybe—this exact experience; the sensation I was feeling was beyond distracting.

Dorothy continued slowly working my shaft with one hand while licking the shaft—then the head in turn—with her very talented, pierced tongue. Every time she’d complete a pass over the head, she take a moment to close her lips over my shaft and look up at me; those looks alone were nearly too much for me to handle.

As Dorothy continued to work my dick, I began to feel my balls get tighter as my cum started to well up. Despite my fast-approaching orgasm, I was suddenly struck by the feeling that something was off. It then occurred to me what was wrong; after all the time I spent thinking about Dorothy, her simply sucking me off—although incredible—felt like a cheat somehow. If we were going to give whatever this was a try, I didn’t want to start off by being selfish.

“Hold on,” I said; Dorothy lifted her head. With a sexy smile, Dorothy asked, “Are you about to cum? Don’t worry about it; you can cum.” Dorothy resumed slowly stroking the base of my cock, and as she was about to go back down on me, I said, “No; that’s not it.” She looked back up confused; not knowing exactly what to say, I—for the second time that evening—just went with what was on my mind.

“After all this time, I want you,” I blurted out. “I don’t want you to think I’m just in this for a fun night. I don’t want right now to be about me when we think back on this night.”

I then realized even this gesture could easily sound hollow; how many guys wouldn’t try to convert a blowjob into intercourse? I suddenly felt dumb and was worried I’d blown it. “I mean, we don’t have to do anything you don’t want to do . . .,” I quickly offered. Dorothy shook off my sentence with a look, and smiled as she crawled up the bed to me until we were face-to-face again. As she looked into my eyes, she said, “I want you, too” with a pure and sincere smile. That smile, truthfully, almost sent me over the edge.

Dorothy kissed me with a knowing passion, and then leaned over me to the nightstand, pulling out a condom and tossing it on the bed next to us. Dorothy eased her panties off, and I caught a glimpse of their wetness as she tossed them aside. On instinct, I immediately leaned in to kiss her as I slowly worked my hand over her moist, warm slit. “That feels so good,” Dorothy moaned, almost gasping as she broke off our kiss, “Keep going.”

I continued to rub her clit before entering her with my fingers. “Oh, fuck,” Dorothy said as I penetrated her. As Dorothy bucked against my hand and her wetness began to coat my fingers, I moved my head down to her chest and began to suck on her breasts. The sweet taste of her now-glistening chest was intoxicating; I followed her chest down to her stomach with my mouth, taking in the scent of her ample body as I went.

By the time my tongue found its way to her clit, Dorothy was moaning and breathing heavily. As I began to lick her clit while still working my fingers in and out of her, I looked up to see Dorothy with her head thrown back and her hands clutching the sheets. Writhing against my tongue and fingers, Dorothy suddenly called out, “Get up here!”

As I made my way back up to Dorothy’s face, again kissing up her body as I went, she began to slide down toward me. Grabbing my dick, she looked me in the eyes and said, “Just fuck me now.”

She reached over and grabbed the condom, tossing it to me. I sat up a bit as I opened and put it on quickly. Just as I had finished doing that, Dorothy nudged me back down onto her bed, then she climbed on top of me. With her hands on either side of me, she brought her lips down to meet mine for a deep kiss while her other lips began to rub against my cock. After grinding her clit and slit against my throbbing cock, she reached down with one hand and pulled me inside her.

I don’t know how I didn’t cum just then. Dorothy slowly eased me in past her tight lips into her deep warmth, moaning as she slid further and further down on me until her ass came to rest on my thighs. Dorothy leaned back over me, dangling her tits in my face as she rode up and down on my dick. I reached up to fondle her dangling tits when I heard Dorothy moan, “grab my ass.”

I did as I was told; I firmly grabbed her ass with both hands while starting to again lick and suck on her bouncing breasts. “Oh, keep going, keep going . . .” Dorothy moaned as her breathing got heavier and she tightened even more on my dick. “You feel so good,” I offered, feeling pre-cum begin to slip from my dick. “I know,” she said with a little laugh.

The sudden confident acknowledgment that Dorothy knew exactly what she was giving me did something to me; I let out a loud moan of pleasure. “I’m going to cum soon, Dorothy; you’re going to make me cum” I said between moans. Dorothy responded to this by starting to ride me harder. Slipping one hand down to her slit, she began to rapidly rub her clit while bucking against me harder and harder.

“Go ahead and cum; cum inside me,” Dorothy moaned as she got even tighter. Wildly flicking her clit more and more, Dorothy’s breathing got even heavier. “Just cum inside me; make me cum, too” she loudly commanded. Looking me straight in the eyes as she began to ride me even harder, she added “show me how much you’ve wanted this.”

I grabbed Dorothy’s waist and started to pump in and out of her as fast and as hard as I could, my balls starting to slap against her as I did. “OH FUCK!” Dorothy loudly moaned. I felt every muscle below my waist tense up as my cock throbbed and my orgasm hit. “OH; I’M CUMMING!” I yelled. Dorothy moaned loudly as I started to shoot my load inside her warm slit. Dorothy then started to spasm, milking my dick rhythmically as she did. “I’m cumming; I’m cumming; I’M CUMMING!” Dorothy yelled as her first wave hit her. “Keep fucking me, keep fucking me,” Dorothy pleaded. I continued to thrust up into her as my own orgasm was starting to subside. I didn’t care how overpowering the feeling was on my then very sensitive dick; I was too busy still enjoying the moment.

“Keep fucking me!” Dorothy continued to shout as wave after wave of pleasure hit her, her body now arched back as she grinded against me. Amazingly, the sight of her still in the throes of her orgasm—her sweaty body thrust forward toward me, her head thrown back—gave my cock back just enough stiffness to continue on. “Oh FUCK!” Dorothy yelled as her final wave crashed down.

As Dorothy’s last wave subsided, she lazily climbed off me and laid down next to me. Neither of us said anything for a long time; what exactly was there to say? I’d never thought I’d have a night like that with Dorothy, and as I sliently laid their next to her, I hoped it wouldn’t be the last.

Source: reddit.com/r/eroticliterature/comments/jegvdw/a_summer_night_making_up_for_lost_time_mf_str8