A Last College Chance

It seemed that the East Coast kids who went to boarding school got a lot of the “sex, drugs, rock and roll” out of their system by college.

Talking with my buddies, it seemed like they’d all had plenty of wild times, including threesomes. I had no idea how a threesome even came about. Were they bragging or bullshiting me? It seemed far-fetched that so many of them actually had engaged in a threesome, and yet… you’d have to be blind and deaf in a dorm not to see the morning “walk of shame” or hear the thumping of headboards echoing down the halls.

In contrast, neither of us were very experienced coming into college. We sincerely considered each other our “first.”

This fact was rather romantic. I felt like I’d found that “special one” when I met Jennifer. We had no doubt that after attending the small Liberal Arts college on the East Coast, we’d return to the West, get married, and spend our lives together. Which was good. The problem was this: the nagging feeling that we had a fleeting 4-year window to be young, wild, and foolish.

Semester after semester, the other students were ticking off their list of sexual experiences, while my girlfriend and I remained totally monogamous, and therefore, comparatively inexperienced.

The first year we were so into each other it didn’t matter. We experimented a lot between us. But by senior year, there was the feeling that we’d done every thing we could between us.

Now our final semester before graduation, we were getting to the end of our college experience with every passing day. Where else would we ever be surrounded by young 20-somethings who drank and had sex as much as they attended class? We felt like it was “now or never” to get our last chance at the free pass of “anything goes” college sex.

When we talked about it, we agreed that we didn’t want to break up. We didn’t want to date others. We just wanted to somehow not end college without some “I can’t believe I did that” story that we could secretly take into adulthood and then look back on with a private smile, a little naughty nostalgia. “Those sure were the days!”

We both agreed we should do “something” wild and even a bit reckless, embarrassing, or genuinely kinky; we just really didn’t know what that’d be, or how to go about making it happen. However, as in the case with most things college, the answer was presented by alcohol. It was at a party.

We didn’t know anyone at the party, and awkwardly drifted from kitchen to living room and back to the living room. Eventually we got bored and wandered upstairs, and then out onto a stone balcony overlooking the grounds. It was late spring, nearly summer, and the air was warm. The evening turned slowly to twilight. Jennifer sipped her drink and looked out over the lawn. Neither of us were used to the “houses” in New England. They were more like 19th century English manors.

Jen wore a vintage sundress. It was a ’70s style, strapless, with the tube-top meant to be held up by the wearer’s breasts. Jennifer’s perky A-cups didn’t offer much support in that way, and she was always pulling her top back up into place. If she had to run, my guess was that the top would fall. I don’t know why, but each time she pulled up her top, it made me want to pull it down even more. Sometimes I even wondered what it would be like if her top fell down in front of everyone, the whole drunken crowd of partygoers.

Looking our across the groomed grass, she said, casually, “I’m not wearing any underwear.”

I slipped my hand down the small of her back. Grazing over her buttocks, I could feel no underwear. “You’re naughty,” I said.

“Ummhum,” she said softly.

Her hips were moving slightly, pressing herself against a corner of the stonework. I realized what she was doing. I’d once walked in on her in the bathroom as she was pressing her hips up against the corner of the pedestal sink. She was mortified at the time, being caught. But afterwards I assured her it was not only perfectly normal, but actually sexy to see her masturbating. She relaxed and admitted that one of her favorite ways to get herself off was to rub up against something smooth and hard.

Now she was standing on the small balcony, quietly and stealthily pressing her body through the thin fabric of her dress against the smooth marble. “You could take me right here,” she said.

“Someone might come out,” I said.

“Then he could watch,” she giggled. She always got a little silly when drunk. Also bolder. Sober, she probably never in a million years would rub up against the stone balcony railing, but tipsy drunk and half concealed by dusk, she was plenty willing. We could here the murmuring din of partygoers from the first floor.

I glanced to see if anyone was near, then reached up under the hem of her dress. I felt her warm bottom, bare.

I continued to reach, slipping my hand slowly and gently between her legs.

I felt the soft pelt of her curls. Once, she had let me take scissors and a razor to her thick brown bush, exposing her thin pink lips. (Afterwards, it gave her ingrown hairs and itched like crazy so we never did it again, but at least she’d let me try; it was one thing we’d checked off our college try list.)

I wiggled my finger, parting the hair, and dipped my finger into her wetness. She was already soaking, warm.

With her clit pressed against the stone, I couldn’t rub her there, but I knew what she really preferred. I slicked my finger with her sticky juices, and then, gently, slid it back up her crease, to the soft, sensitive skin of her rosebud. She shuttered to my touch, but rocked her hips further back, giving me a better angle.

I circled my finger around her wrinkled skin, lubing it with her own juices. Then, with a slow, but firm push, I wiggled my fingertip inside her backdoor up to my first knuckle.

She gasped.

I waited and let her clenched muscles relax. She continued to slowly hump the stone. Her ass was incredibly tight. In fact, after dating for three years, she’d finally agreed to let me try anal with her. We were able to get just the tip of my penis inside before she begged me to stop. She cried it was so painful. We hadn’t had anal sex, but she had at least been open to the idea. And she did, in the process, discover that she actually enjoyed anal stimulation–especially my finger. We kept a bottle of lube by our bed, just for that.

She exhaled deeply. I felt her muscles relax. “Ok,” she said.

I pushed a little further, pressing my finger into her up to the second knuckle. This caused her to moan.

“Yessssssssssss,” she said quietly under her breath.

She continued to roll her hips against the smooth stone to stimulate her clit, while I slowly matched her rhythm, working my finger gently in and out of her butt.

“That’s nice,” she whispered.

“Tell me what’s happening,” I whisphered. This was one of our new games. At first I’d asked her questions like, “does that feel good?” She’d say yes or no, and it was good training, mechanically, of how to please her. But I learned that when I’d asked her more open-ended questions, she could reveal deeper fantasies.

I first discovered it when we were in bed and I was very gently grazing just the tip of her clitoris with my finger, trying to be as soft and light as possible. It was obviously making her writhe with pleasure, so I didn’t ask if it felt good. Instead, I said: “Tell me what’s happening.”

To my surprise, Jennifer said, “She’s licking me, using just the tip of her tongue.”

Jen had never had a bisexual experience, but, she later revealed, she often used it as a fantasy when masturbating.

So as we stood on the dark balcony, Jen pressed up agains the marble rail, me standing behind her, my hand secretly slipped up under her dress, my finger pressed inside her butt, softly sliding in and out, I asked: “what’s happening?”

“I’m being taken,” she whispered.

“By whom?” I asked.

“A stranger,” she whispered. “I don’t know his name. I don’t even know what he looks like. He just came up behind me…”

This was new territory. We’d mutually fantasied about her with another girl, but never with another guy.

“And he found me rubbing against the stone here, and he saw what I was doing…” She paused as she gasped with pleasure, then continued: “and he just pulled up my dress, without asking.. he just… he….”

“And he saw that you weren’t wearing any panties,” I added.

“Yes,” she said.

“And he knew you were a naughty girl, and wanted to be fucked…”

“Yes!” she said, gasping for breath. The intensity of her hip gyrations increased, and from the clenching of her ass around my finger, I could tell her orgasm was nearing.

“What did he do next?” I prompted.

“He took me,” she moaned.

“How?”

“Like that,” she said.

“Like this?” I asked, and drove my finger into her butt.

“Yes,” she cried, “like that.”

“What did he do?” I asked, wiggling a second finger into her butt. “Did he stick his cock into your ass?”

The combination of the second finger and the dirty talk really got her. She cried out, “Yes!”

“And what did he do? did he fuck you in the ass?”

“Yes!” she screamed. “Like that.”

“Tell me,” I said. I rammed my two fingers in and out of her.

“He fucked me in my ass,”

“In your virgin ass?”

“Yes, he fucked my virgin ass…” she was panting and bucking her hips, driving my fingers deeper. And rather than tighten, her butt muscles seemed to relax, to allow my finger to penetrate deeper. I was finger fucking her hard in the ass, in and out, in and out, and I knew she was right on the edge of a climax.

I knew a few words could push her over the edge.

“He’s fucking you in the ass,” I said. “He’s taking you as he wants…”

“Yes,” she said.

“He’s fucking you as hard as he can. He can’t hold off any longer.”

“Yes,” she cried. “Please give it to me!”

“He can’t stop,” I said. “He’s cumming in your ass!”

With that, I jammed my fingers deep inside of her and moved them like a cock ejaculating inside her rectum.

She began to shake. Suddenly the wave of orgasm washed over her. And she was quivering in a powerful orgasm.

After her spasms relented, I slipped my finger out of her, and smoothed her dress down. She raised herself off of the marble rail and steadied her shaky knees. Her face was rosy. The casual observer might think she was just flush from alcohol, but I knew she was glowing from her secret orgasm.

I was, of course, hard as rock under my pants. I wanted to take her, lube my cock with my own spit and force it into her ass, taking her right then and there. It might cause her pain at first, but sometimes I thought if I could just get my cock in past the ring of her tight muscles, It would slide easily the rest of the way. Two fingers was a new first for us, and she’d taken it well. Surely it was the next step to actually having anal sex. But I knew we’d already pressed our luck with privacy.

In fact, just at that moment, we heard, “Oh hey guys.”

We turned and saw our old friend Mark.

Mark had been my Freshman roommate, and he’d known me before I’d met Jennifer. When I met Jennifer, the three of us hung out on the first few dates. (You know, have a buddy there to make it less awkward, more of a group thing, not a “date.”) There was a lot of flirting at the time, because I was so attracted to Jen, and she to me. Though I always felt like maybe she was flirting with Mark, or that he would have gladly moved in on her had I not already claimed “first dibs.” At the time it made me really jealous. I wanted Jen all to myself, and felt stung by the innocent flirting between Jen and Mark.

Maybe I felt a little insecure, too. We were only 18 at the time, and I didn’t have as much confidence in myself. And at that point, Mark and I both knew Jennifer equally. She really could have picked either of us. Maybe that’s why I sort of stopped being friends with Mark after Freshman year. We didn’t have a fight or anything, but after we weren’t assigned to live together, I sort of let us drift apart. Sometimes it wasn’t even conscious, it’d be as simple as just spending more time with Jen. If we ran into each other, we’d say, “yeah, we should hang out.” But it never seemed to happen.

So, three years had passed. And Mark was standing in front of us, smiling, also a little drunk, hi-fiving me and saying “Dude! how ya been?”

He turned to Jen and gave her a big bear hug. I braced myself for the electric shock of jealously, but for the first time, it didn’t come. I just smiled, relaxed. Maybe more confident in myself, or more mature. Or maybe I was secure in the fact that Jen had been dating me exclusively for three years and we knew we were in love. I didn’t even care that their hug seemed a little long, or that he seemed to squeeze her against him.

It was like old times, and we instantly fell into the comfortable conversations about movies and tv shows and classes and teachers and just other silly things. It felt good to be hanging out and have someone to talk to at the party, and enjoying how easily we laughed together.

As we chatted and laughed, I noticed Mark kept glancing at Jen’s chest. The evening had set, and it was now cold outside, and her nipples were poking against the thin fabric of her dress.

Jen noticed, too, and teasingly asked: “Whatcha lookin’ at, Mark?”

He’d been caught, but instead of being embarrassed, turning red, or apologizing, he asked: “Did you get your nipple pierced?”

Jen laughed. “Yeah,” she said. “Last semester.”

Jen has extremely sensitive nipples. She can almost cum just by having her nipples sucked. So for me, it was no surprise when she announced she wanted to get her nipple pierced. (This might date us, but piercings were really popular and common those years we were in school.)

Mark shook his head in disbelief. “I never would have thought…” he said, trailing off his sentence, now looking directly at the fabric stretched over the small cups of her breasts.

I guess I should probably admit that Jen and I first met through a college church group. She’d grown up in a religious family in Littleton, Colorado, and I’d grown up in a tiny little town in Wyoming. I wasn’t especially religious, but church was the one way I had grown up learning to socialize. The picnics, the meetings, the volunteer service created an instant network of friends. I’d felt so lost in the East, that joining the college church group Freshman year seemed like a good way to meet people. And it had worked. I met Jennifer.

So, when I’d introduced Jen to Mark Freshman year, he’d basically met an 18-year-old church-going virgin. He knew her as the young girl from the Rocky Mountains who had never been back East, who studied a lot, and read, and got straight As. The girl who had a somewhat plain, tomboy body and mousy brown hair and glasses.

He never knew about the time Jen let me take photos of her naked. Or the time we were driving all the way back to the Rockies for break, and she opened my pants and sucked me right then and there as we sped down the highway at 55 mph. He didn’t know that she’d discovered a love of anal play, and that her very favorite kink she’d discovered is that she loves-loves-loves to be tied up. Or the first time we went camping, before we’d even “gone all the way,” and she gave me a hand job and let me cum on her small breasts.

I really can’t explain what happened next. I’ve thought about it a lot over the years. The only thing that even comes close is 8th grade. The playground. I had a huge crush on a redhead girl named Mandi Clements. She never liked me back, and this made me only tease her all the more. I had no idea how to socialize with her, or get her to like me. Somehow I thought tormenting her, stealing her backpack, juvenile things would get her to like me.

The thing that the guys did back then was to “pants” each other. One guy would be the distraction, and the other slip up behind the victim, and yank down his pants. It was “horseplay” as they called it, and we never got in too much trouble. “Boys will be boys” is how we were raised in Wyoming.

Unfortunately, I aimed my mischief on Mandi. When I came up behind her, I yanked down her gym shorts. I expected, at best, to get a glimpse of her white cotton underwear. To both of our surprise–shock and horror, really–her panties came down with her shorts, and in plain view to the other students, and to the teacher, was a briar of curly copper hair. None of the boys had ever seen anything like it.

Mandi yanked up her shorts, and ran off crying. At that exact moment, the teacher latched my by the ear, and marched me to the principle’s office.

I could have been expelled from school, but instead, I was suspended for a week, had to apologize in person to both Mandi and her parents, and then had to give an apology to the whole school assembly.

Given that background, you’d think I’d learned my lesson. Apparently I hadn’t. Somehow, drunk on the balcony with Jen and Mark, an impulse from 8th grade shot through me. I yanked down the top of Jen’s sundress, exposing her two small breasts, and the nipple with the small silver ring.

To my surprise, she just giggled. And then yelled, somewhat delayed, “Hey!”

“Nice,” Mark said. “That’s actually really hot.”

“Really?” asked Jen. “You don’t think they’re too small.”

Mark of course had been talking about the piercing, but Jen’s mind had gone to her breast size, a topic she wasn’t always the most confident in.

“No, no, no,” said Mark. “They’re perfect.”

The compliment must have worked. Jen smiled and blushed even more. It didn’t really sink in to any of us that at least a minute must have passed and Jen was still standing outside on the balcony with her top down, her pale breasts almost glowing in the moonlight.

“I’ve never seen a pierced nipple,” Mark confessed. “I mean, not in person. In hot photos, yeah, but not up close.”

Perhaps it was the phrase “up close” that stood out. But Jen offered, “Well, look as close as you want, I guess.”

Mark didn’t need to be asked twice. He glanced at me, but I must have been beaming like an idiot. I was sort of proud of how bold Jen was, and how much confidence she was gaining. I’d always loved her little firm breasts. In fact, they seemed like they should be called “titties”or “boobies”to express their youthful, petiteness.

Mark leaned in a little closer, eye level with her breasts. The cool evening air pinched her nipples hard.

“My breasts are so sensitive,” Jen said, not really to anyone in particular, just more as a matter of fact.

“Yeah, she loves to have them sucked,” I said, proudly. As if her boobs were mine to show off and brag about.

“Can I?” Marked asked.

I don’t think either Jen or I expected this. But Jen glanced at me and looked at me with the “I’d really like that,” look of glee I’d seen when she’s excited about getting something. And I, a little slow, a little buzzed, and (admittedly horny), just sort of smiled like an idiot.

Mark leaned forward and softly kissed the tip of her nipple, as if politely kissing someone on the cheek in greeting. When she didn’t retract, he kissed again. She let out a little “oohh,” squeal, encouraging him to lean forward and take a breast into his mouth.

From the way his jaw worked, I could see that her was gently sucking her breast, while flicking her nipple with his tongue. This caused Jen to writhe and moan. She was in pure extasy. When she yelped, I knew that he’d gotten a little bold and nipped her tit with his teeth. I knew she loved a little pain when it came to playing with her breasts. Sometimes when we fucked doggy style, she’d ask me to lean forward and pinch her nipples hard. The harder I pinched, the harder she would climax.

Her head was titled back, eyes closed, mouth slack, as he nibbled, sucked, and slurped her little boob in his mouth.