[MF] Thinking with the small head

When I was a college sophomore many years ago, it was a period of time when the Pill was widely available and STDs were rare, at least among my peers at college. I’d lost my virginity as a freshman to Leann, a longtime girlfriend I’d had in high school. She was a year behind me and attended a different high school. We’d done most everything except PIV intercourse when I was a senior and she a junior, our reluctance stemming from an fear of pregnancy. Early in my freshman year she phoned to tell me that her mother had taken her to a doctor to get a prescription for the Pill – to “regulate her period” was the rationale, perhaps just for Leann’s father’s benefit, as her mother probably noticed our increasing physical intimacy and wanted to ensure that “regulate” meant “keep occuring.”

Leann and I fucked several times during that school year. She visited me a few times and spent the night in my dorm room, and I’d occasionally go home for the weekend and we’d find a private place for a quickie. Things continued through that summer, but our time together came to an amicable end when she enrolled at a college 1000 miles away. I could go into more details about Leann, but my story now is about what happened next.

So there I was as a 19-year-old horny college sophomore, who’d enjoyed the previous year’s bareback sex with a steady girlfriend and wanted to find another girlfriend – this time local and more frequent. I was now living in an apartment with roommates, and that meant no hassles with sneaking a girl into the dorm for an overnight.

As luck would have it, when waiting in the Fall Registration line, I encountered Cathy, who was someone I’d known casually in high school, though never dated. She was shorter than Leann, with a more curvy body and long, brown hair that flowed down to the middle of her back. We hit it off quickly and began seeing each other a few times a week, on campus or at my apartment or at her dorm. Friendly conversations soon became makeout sessions. The first time I tried to touch her breasts, Cathy stopped me and told me her intention was to be a virgin on her wedding night.

Do I sound shallow when I say that I wasn’t pleased hearing that? I really didn’t want to trade a happy sexually intimate relationship with Leann for a chaste kissing-only relationship with Cathy, though I was willing to continue a relationship with Cathy to see how dedicated she really was to maintaining her virginity. After all, my college peers were losing their virginities left and right.

As it turned out, over the following weeks Cathy surrendered more and more of her body to me. Before long our makeout sessions included caressing her breasts, at first shielded by her bra and blouse, and within a week she allowed my hands and mouth on her bare skin. An unbuttoned blouse and unsnapped bra transitioned to her being topless in my bed, then to both of us being topless. Then the above-the-waist limitation yielded to below the waist and allowing my hand inside her panties, then to her panties on the floor and to my nose and tongue spreading her succulent labia wide and teasing her vaginal opening.

Eventually the inconvenience of clothes led us to both being naked in my bed or hers, with our hands and mouths freely touching and caressing and licking and sucking each other. And when Cathy was comfortable with that activity, she would mount me and glide her slick, inflamed clit and labia up and down against the bottom side of my erection, or I’d mount her missionary and stroke my cockhead up and down her cleft.

Cathy never climaxed, despite my best efforts as a not-too-experienced 19-year-old with my tongue and with my cockhead, though she’d always get joyously aroused. When I was on top couldn’t hold back any longer, I’d warn her I was going to cum and move my hips a few inches higher to spurt my hot liquid on her tummy, while she would pant moistly in my ear and her hands would hold my ass and her legs would wrap around mine with a tight grip.

We kept this up for another few weeks. When I suggested that Cathy visit the Student Health Center to get on the Pill, she said no. That would be an admission that we were going to have intercourse, and she still wasn’t comfortable going that far. She did go to a drug store and buy contraceptive foam, just as a measure of added protection to my precum close to her vagina and my semen on her tummy, and she’d squirt it into her vagina between my cunnilingus and our faux-intercourse. During foam-protected sessions, she did allow me to hover at her opening every few strokes and just _barely_ penetrate her snug muscle ring a quarter-inch or a half-inch, pausing there a second or two before withdrawing and resuming my steady stroking of her yawning labia and stiff clit.

And even though I now had regular no-PIV intimacy with her, and even though I was having regular orgasms, I still was frustrated at her restrictions. I imagine she was frustrated, too.

It was around that time that Cathy went home for a weekend visit, and that Saturday evening I went to an on-campus dance. It was there I met Lisa, who was a sophomore who’d transferred to my college from a Boston school earlier that Fall. Lisa was similar to Leann – a trim body, short hair, and a bubbly personality. We talked, we danced, and we talked more. During one slow dance she told me that she’d lost her virginity to a boy she’d met in Boston who went to the University of New Hampshire. She’d gone to visit him there, and they’d spent the weekend in bed together, she confided with a big grin. After a couple of fast dances, we again joined for another slow dance, during which she asked me where she could get a prescription for the Pill. Ever so helpful, I told her that the Student Health Service was the place to go.

So now I knew three things about Lisa: she wasn’t a virgin, and she was comfortable enough with me to tell me that and tell me that she enjoyed sex, and she was going to start taking the Pill. I could only presume she intended to have sex again – and maybe with me!

Shall I remind you that I was a horny 19-year-old, familiar with the joys of full PIV bareback intercourse with a previous girlfriend, Leann, and now discouraged and frustrated with Cathy’s halted surrender of her body with seemingly everything except for full PIV bareback intercourse?

After that weekend, Cathy and I resumed our naked dances, and Lisa and I got together for a few platonic study dates. One afternoon I was at my apartment when the phone rang. It was Lisa. “Remember our conversation about me getting on the Pill?” she asked. Well sure, I remembered. “I did it. Do you want to take it for a test drive?” Uhhh, what do you mean exactly? “I mean I could come over and we could… you know… fuck.”

And that’s what happened. A half hour later Lisa was at my door, and 10 minutes after that we were naked in my bed. Her body was delightful, with nice handfuls of breasts and a thatch of trimmed pubic hair (as was the almost universal norm back then) and fat, juicy labia with a jutting clit that just begged to be sucked. We kissed and caressed, she went down on me (which was a first) for a few minutes, and I went down on her for even more minutes until she tugged at my shoulders. “Inside me,” she grunted between quick, shallow breaths.

And so I did. I mounted her missionary, slid into her ever so tasty and creamy vagina, and we got into a rhythm together. It was slow at first, and her hips rose to meet my downward thrusts. Her eyes were open wide and glued to mine, and her mouth pursed in an ‘O’ as her panting got quicker and quicker. Her vagina got more and more juicy, and her giggles and moans became groans and grunts and high-pitched little whimpers that got more frequent and louder. And most amazing of all to me was that when Lisa’s arousal reached the same plateau reached by both Leann and Cathy, Lisa’s arousal blew past that plateau, and a minute or two later she crested in a noisy, shuddering, squirming orgasm, followed a several seconds later by my hard-thumping muscled final thrusts and one ultimate deep, driving push, and an explosive series of my liquid pulses into the far reaches of her vagina.

Lisa and I managed a second session that afternoon, this time with her on top, and that time she managed two happy, squealing orgasms before I unloaded another large volume inside her. When our heartrates came mostly back to earth, Lisa sat up and my softening erection plopped out, followed by the obvious leakage of white from her vagina. “Oops!” she laughed. “I hope those Pills work!”

Lisa and I didn’t get together again. She knew that I was seeing someone else, and she acknowledged that she did just want to sex with me as a “thank you” for my earlier special new-student orientation. She was looking to enjoy more young men with the safe comfort of the Pill.

Meanwhile, Cathy and I continued our faux-intercourse. It had become even more frustrating, now that I’d experienced a reminder of what a real adult sexual relationship was all about. Now when I was on top, the forays of my cockhead into her the outer reaches of her vagina were more and more frequent and increasingly obvious. I’d sometimes get my entire cockhead inside her outer muscle ring and remain there momentarily. Cathy never objected to these subtle incursions. There was never a “No” or “Stop”. Though neither was there a “Yes” or “Deeper.”

One evening in the dead of winter I couldn’t hold back any longer. The penetration of just my cockhead became penetrations of a quarter of my erection, then a half of my erection, and my withdrawals weren’t total. I pulled back until just my cockhead remained inside her vagina, then I thrust forward again with another shallow penetration. As always, Cathy’s arousal rose to her typical plateau peak, her breaths were fast, eyelids shut, her exhaled moans announced her pleasure.

When I was close to climax, I plunged into her twice, my pubic bone bouncing against hers, and then withdrew fully and spurted onto her belly between us in my usual manner, while her hands and legs embraced me in her usual way. And for the first time I felt like we’d had a breakthrough. When my erection died, I lay beside her, cupping a breast. I spoke first. “So, now you’re not a virgin. Really and truly, you need to get on the Pill to be safe.”

Cathy looked at me. “I still consider myself to be a virgin?” What? Why? I’ve just been all the way inside you! She explained, “Because you’ve never actually cum inside me. So I’m still a virgin.” I pondered that logic for a moment. Yet again my frustration level increased. Just when I thought that Cathy and I had finally, _finally_ crossed PIV threshold, she had created what seemed to me to be yet another rung on the ladder, still unclimbed.

My 19-year-old brain ruled the day. When we resumed our lovemaking for a second round, after kissing and fondling and me going down on her until her hips were squirming and her murmurs became gasps, I mounted her yet again. This time I only grazed my cockhead between her labia with a few gentle strokes before I deliberately, clearly and without any misinterpretation, slid the full length of my erection into her vagina. Cathy’s eyes widened, and her legs remained spread wide, knees raised, and her hands brushed up and down my back. Did she want this? She seemed as though she fully accepted this. I told myself that she wanted _me_ to make the decision to proceed, so _she_ wouldn’t be responsible.

Now my strokes were steady and deep. In and out, in and out. No teasing withdrawals. No subtlety. “I know what you’re doing,” she declared.

“Yes,” was my only response. In and out, in and out. This time I wasn’t trying to make this a lengthy session. This time I was going to enjoy her warm, slick vagina. This time she was going to feel my climax in a way that she’d never before experienced. In and out, in and out. I was getting closer and closer. “Here I cum,” I managed to grunt as my erection stiffened and I gave my hips that final firm, I-need-to-get-DEEP thrust, and I pulsed my fluid, again and again, into Cathy’s vagina.

I remained inside her as long as I could manage, then rolled to her side. “So,” I said.

“So,” she replied. “I guess we’re now engaged.”

“We are?”

“We’ll get married after graduation.”

“We will?”

“And we need to stop everything we’ve been doing. We shouldn’t be naked anymore. Not until we’re married.”

“Uhhh….”

“I’m going to tell my parents that we’re engaged!”

Cathy and I broke up two weeks later. We remained friends – sort of – but we never spoke again about the relationship we’d shared.

Source: reddit.com/r/gonewildstories/comments/5pt3em/mf_thinking_with_the_small_head