With Wendy's Guidance

First, total disclaimer: this hasn't ever happened, at least not to me. I've been writing erotica off and on for a while, and at least one old girlfriend used to masturbate herself frenziedly, listening as I spun smutty tales for her amusement. I'd actually intended it as a prose exercise, trying to write about something with which I had no personal experience, and imagining everything, making it as real to my readers as if I had really done everything I relate below. Let me know what you think, and feel free to vote for my story if you like it. Above all, enjoy!

ScottieDog61

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It happened in my sophomore year of college, away from home and on the road for my college debate team. My girlfriend Wendy was almost four thousand miles away, back East to visit her family over the spring break.

We had started up in November, dating a couple of times before falling in love, and later into bed together. We spent most school nights apart, and the weekends from Friday on through Sunday afternoon in my dorm room, or her apartment, fucking like crazy. Now, in early April, every minute away from her left me longing for her touch, her kisses, the taste and scent of her juices on my tongue, and the sight and feel of my cock gliding in and out of her while she moaned my name or throaty, endearing four-letter words in time to our thrusting.

Being twenty is wonderful, especially in retrospect. Just past the embarrassment of getting an unexpected hard-on when standing up in front of the class, or in the pool with my sister's friends, where even the cool autumn nights and the frigid pool couldn't keep my flag from flying, and my sister blushing while her friends giggled, pretending not to notice. At twenty, you can actually get laid without hiding from your parents, or skulking around a backyard hoping her father doesn't catch you with your pants down and your cock filling your girlfriend's tender young pussy, or, worse, her mouth.

Wendy was a good lay. Actually, she was an awesome lay. Her body was slender but generously curved in the right places. Her glorious mane of red hair spilled down over her shoulders, and when she rode astride me, grinding her sparse, almost pink bush against me, her pussy devouring my cock, nipples playing peek-a-boo through her tresses, I felt like I was in Heaven, or a really good porn flick.

She seldom sunbathed, but when she did, it was always in the nude, and only in the late afternoon so she wouldn't burn her pale, satiny skin. She had dark blue eyes, mischievous and bold, and slender lips that were much fuller and stronger when they touched mine. Her breasts were of average size, but full and responsive to my touch. She usually wore overalls with a tee-shirt, and sometimes a sweater for the chill Bay Area winters, and, on one notable occasion, nothing but the overalls. For about five minutes, that is.

I was her first lover, her first all-grown-up relationship, and she tried to be a young sophisticate, almost succeeding until her first giggle broke the spell. My cock was the first inside her, so she said, but she was a fast study, picking up all the tricks I could teach her and she could read about and watch in the occasional porn we'd bring back to her apartment, feeling very adult while looking for any excuse to stop the movie and get our clothes and any waiting out of the way.

I'd had three women before her, none lasting in my life longer than a few weeks, followed by late-night masturbation sessions going on until either the sun rose, or I fell asleep from happy exhaustion. Even then I dreamed of their bodies, always more perfect and willing in my sleep than in real life, rubbing and kissing and sucking me all over, begging me to return to them. More often than not, I woke to the sound of my own soft, covetous moans before school, naked on top of the bed, with my shorts mysteriously on the floor, humping my fist or the pillow in dreamy consolation.

Wendy was new to sex, and despite her eagerness was very tentative about a lot of things. The first time I kissed her bush, she looked surprised, and had given me one of those, "Is that supposed to do something for me?" looks. Her first orgasm happened the second time I ate her out, and she seemed to decide that it did, after all, do something wonderful for her. To thank me, she very gently tried to fellate me, again looking puzzled at my reaction to her lips and tongue on my shaft. Like a lot of guys I knew, she clearly preferred receiving oral to giving it, but dutifully sucked me off, letting my semen spurt onto her lips, and a couple of times actually in her mouth, perhaps in the mistaken belief that I wouldn't go down on her again if she didn't reciprocate.

As if.

Anyway, Wendy was off to see her family all the way across the country. We promised to call every couple of days, but not every day, because that would be too needy. During the quarter break, I was out of town at a debate team tournament, and my school was in good shape to place in the week-long event. My roommate was an old friend, and the captain of our speech forensics team, James. I'd caught him stealing sidelong glances at Wendy when we were together, and sometimes smiled back, conspiratorially, telling him in my own mind that she was everything anyone could ever want.

But this story is about what happened when she was away.

James was lean, but in a wiry way, not skinny or frail. He wasn't a jock, but he worked out often, battling the tendency of a student schooling away from home to gain or lose weight with the change in diet and schedule. His black hair was cropped short, and he had tightly trimmed sideburns. His clothing favored darker shades, often a black button-down shirt and blue jeans, or shorts and a tee with sneakers when he went to work out. His most striking feature, which endeared him to women of all types, was his eyes, a deep yet clear blue, the color of the ocean under a perfectly blue sky.

We'd arrived Sunday at the hotel and unpacked. Monday kicked the festivities off, and Tuesday morning found my school tied for second place so far. My own debate on the merits of public funding for housing helped us get to that point, and I had called Wendy as promised that night, as I had Sunday. This time it was without success; the phone machine answered, and I checked my watch, suddenly realizing that just after dinner in Los Angeles was around bedtime in Boston. I apologized to the machine and quickly hung up.

Sometimes, being twenty and horny isn't so wonderful. Unable to reach Wendy, and not willing to piss off her old man, who I was sure was twice my height and nicknamed Killer, even though he was a music professor, I chatted with contestants from other universities, including a gorgeous brunette named Maria, an olive-skinned exchange student from a Latin American country whose name barely made an impression as we moved on to other subjects.

My fifth beer of the evening hit me hard, and I decided to head to bed. Climbing under the covers, I noted James wasn't there, and assumed he had enticed a woman into letting him spend some time in her bed, or just in her. After all, that's at least part of the reason for these competitions, at both the high school and collegiate level.

In minutes, I was fast asleep, but not comfortably. The alcohol interacted with my disappointment over not speaking to Wendy, or hearing her voice, and my dreams were both erotic and dark. In one dream, she stood nude, arms and legs apart to welcome me, and blew away at a sudden gale of wind that sucked her into the black clouds overhead.

That dream passed, and she was with me again, naked and gorgeous, hair fuller than ever before, and her hot kisses stole my breath away as she mounted me, rocking her hips and fucking me deliberately and gently, leaning back with her hands on my knees, arching her back as I started to moan and thrust into the waiting moistness. The walls of her cunt tightened around my cock, and I groaned loudly as I shot my load deep into her waiting hole...

I awoke, naked on top of the bed, with the covers thrown back, warm cum on my fingers and stomach, cooling in the hotel room's dimness as my balls continued to spasm, subsiding with each new trickle of semen. Glancing over at James' bed, I was relieved to see that it was empty, but then I noticed it had been slept in, just before I heard the shower turned on. At least he was in the bathroom while I was jacking off, I hoped. Retrieving my shorts and cleaning up as best I could, I got back under the covers moments before James stepped out of the bathroom.

Turned away and pretending to sleep, snoring softly, I listened as he dropped his towel and got dressed. He stopped for a moment, probably grabbing his watch, and left the room without saying a word. Good, I thought. He didn't catch me getting myself off. I hoped I was right.

After waiting to make sure he was gone, I slipped out of bed and got into the shower myself, washing away my semen and all the fatigue I still had left. Dressing quickly, I went downstairs for breakfast and the daily assembly, then on into the day.

Wednesday, despite my troubled sleep and too much beer the previous night, went very well. I placed first in my debate that day, and when the schedule came out that afternoon for the semi-finals on Thursday and Friday, saw to my pleasure that I wasn't scheduled for anything, team or solo, until Friday afternoon, when I had one of each. I had the time off to relax and prepare. Best of all, nobody glanced at me with humor, or whispered behind my back about jacking off, so far as I know.

James and I had dinner at one of the food court restaurants in the quad, and chatted about the tournament, and our chances in the rest of the tournament. I felt relaxed, and certain I would be ready for Friday's events.

Mid-burger, James looked at me. "Dude, you talk in your sleep."

What did he hear? Fighting back a wave of shame, I answered levelly, "I do? What was I talking about?"

"I think you were having a nightmare about Wendy; you called her name a couple of times, but not too loud. It woke me around four, but you calmed down and went back to sleep, and so did I."

"Did I say anything else?" I was nervous as hell, but he just shook his head innocently.

"You didn't sleep too well." It wasn't a question.

"No, not really."

"Thought not. I fiddled with the schedule to get you tomorrow off. You've got to be on top of your game if we're going to win!"

Right after dinner, just before six, I called Wendy again, but again got the machine, and felt like an idiot stammering through another message. This wasn't even one of the nights I was supposed to call, which made me feel even more foolish for being disappointed she didn't answer.

That night, I stopped at two beers, this time in a suite one of the other teams had rented for a night as a party hang-out, somehow keeping it from the faculty advisors of the rest of the schools, and their own. Looking for the bathroom, I stepped into the suite's bedroom, and saw two students on the bed, fucking fast and hard with a minimum of clothing removed, a quickie to burn off steam until they could get to a private room. I shut the door, but not before noticing the woman on bottom was Maria, the exchange student from the previous night.

I made my way to the room, determined to sleep more soundly tonight. Thankfully, my sleep was quieter, and when I woke up Thursday morning, James was in his bed, and my shorts, thankfully, were still on, my cock only semi-hard from the effort of waking up, and nothing else. I crept into the bathroom, stripped, showered and shaved, feeling better rested than I had all week, and ready to dash downstairs and relax while studying my materials for Friday.

James was already out of bed, and stepped into the bathroom, giving me a polite nod along the way. I heard the shower start up again, and I started picking from my books for what to review before lunch. My thoughts must have been fairly deep, because I noticed the shower was off, and James was out the bathroom door, towel around his waist, and heading for his bed.

"How are things? Better?" He didn't usually talk in the morning, so his sudden relative outburst startled me for a bit.

"Yeah. Better. No more nightmares."

"Good! I need you in top form, and so does the team."

He came over to the hotel desk by the window, and leaned over the desk. "What are you doing? This is your day off."

"It gives me a shot at getting a leg up for tomorrow, or whatever mangled metaphor you want to use."

"Shot? Leg up?"

I was starting to feel on edge, but forced it away, and looked up at James from my chair. "Sorry. It's just that I haven't heard from Wendy, and I think I fucked up by calling so late on Tuesday night. I hope I didn't upset her, or piss off her"—old man—"family."

"I'm sure everything's fine. It's probably why you were jacking off all night."

Wha-a-at? "Um, what...I mean...um..."

"Relax. Everybody does it. Wendy's not available, and you're probably pretty horny, and the distraction from the tournament probably did you some good.

"I know watching you did me good."

My heart started to thunder in my chest, and I must have been staring, because he laughed a short bark of a laugh. "You saw me?"

Laughing again, he answered, "Hell, yeah! I nearly came just watching you the first time..."

"The first time?"

"The first time, yeah. The second time I got really hot, and when you started jacking off, watching you humping the air like that, I sat on the bed and got myself off. Wendy must be great in bed for her to get you off like that in your dreams."

"Um, yeah." It felt more surreal with every passing moment, and I had noticed two things that had me frozen to my chair. First, my cock was rapidly awakening, and was bent at an uncomfortable angle in my pants. I started to shift in the desk chair, but stopped suddenly when the fabric rubbed against my shaft, quickening my erection. Second, I noticed James was also getting hard, and his cock was starting to press against the towel around his waist. "So, I came twice." I could barely speak, hardly move, and wondered where this was going.

"No, three times. When you started again, I got up and went around the corner and into the bathroom. When you came again, the door was closed, and I jacked off in the shower while listening." He looked down at me, and I became uncomfortably aware that he could see, and probably was staring at, my crotch.

"So, Wendy's good, huh? You're still horny, though. Right?"

I thought about saying no. "Yes. Very." I didn't realize it until I'd spoken, but my voice was husky with need, and I was almost panting, thinking of Wendy, and putting my cock inside her, and sucking James' cock while fucking her. "Very," I repeated, turning to face James.

"Me, too. Haven't fucked for a few months, and you got me very...hot!" With the last word, he let go of the towel from his waist, and it slid with a whisper of cotton to the floor, as James stood in front of me, hands on his hips, his fully erect cock straining at vertical, right before my eyes. James' eyes met mine, and neither of us moved or said a thing for several seconds, maybe a minute.

James almost whispered, and his voice caught once or twice when he finally spoke. "You want to watch me? Get myself off, I mean?"

I blinked, and couldn't quite say anything. He watched me jack off, a couple of times. It's only fair, right? "Um, it's only fair. Right?"

He grinned broadly, trying to put up a good front, even though he had to be more nervous than I was. Closing his eyes, he stood up straight, took a deep breath and wrapped his fingers around his cock, squeezing more than rubbing it, and said, "Right. Fair!"

I thought he was going to lie back on the bed, the position I'd displayed while giving him my one-man self-fuck on parade. He didn't move anything but his hand, starting to move it very gingerly and slowly up and down the length of his shaft. Sliding all the way down the shaft until his little finger was almost enveloped by his hairy sack, then gliding slowly up, until the head was in the center of his palm, he kept a slow, sensuous rhythm, almost massaging his dick.

James' breath became deeper, but still slow, and I caught a flutter in it at the end of one upstroke. His belly clenched, perfect six-pack abs tightening even as the mushroom shaped head of his cock darkened almost to purple, aroused from the loving friction he was giving it. James was breathing harder now, but still in control as he sped the tempo of his solo dance. He began to pant softly, and puckered his lips to blow out, making a soft little "oh" with each exhalation.

If I'd closed my eyes, I could almost have imagined Wendy moaning instead of James, but I couldn't tear my eyes away from the sight before me. If Wendy were watching me...but I'd never performed like this for Wendy. She'd never seen me naked and playing with myself, and I wondered if she would like to watch me some time. My attention went back to James' efforts, and I felt a quiver in my chest.

My own cock, fully recovered from my triple play two nights before, only slightly stiff just moments before, was tight against my slacks, threatening to burst out of the zipper. I couldn't tear my eyes away from his throbbing member, even as I wondered what would happen when he came, how far his cum would reach, how much of it would get onto my shirt, or my face. The rationalization was easy; I should get my clean clothes out of harm's way, shouldn't I?

"I'm taking off my pants now. Okay?" I couldn't believe I'd said it, but, without waiting for an answer, my hands flew down to my belt, snap and zipper, with a self-assurance I didn't feel, and unfastened everything. Lifting my ass off the chair, I whipped my pants and boxers onto the floor, and sat naked except for my shirt, in front of another man wearing only a little less, ready to watch him cum.

Or you can help him cum, came the thought, lazily, almost sneakily.

Before my thoughts caught up to the reality of my need, I was whipping off my shirt, and, naked as James now, leaned forward until the head of his shaft was an inch or two from my face. I didn't think he noticed, then I saw a pearl of pre-cum grow at the tip of his cock, and James started to work harder. When I cradled his balls, he glanced down in surprise, and closed his eyes again, nodding slowly, giving me permission to help him finish.

My left hand massaged his balls, and I felt them gently, knowing from my own practice at jacking off just how much pressure to bring with my fingertips and thumb. Although he was still jacking steadily, his grip loosened, leaving room for my right hand to scoot underneath, then to guide his fingers away, in moments taking over the chore from him. I was gentle with his manhood, because Wendy was always careful with mine.

Now what? I'd never done this before, but I knew I needed to finish him, needed to milk cum from his balls and cock. I wondered if I'd be ashamed or embarrassed afterwards, and didn't care enough to pursue the thought very long. My own member was tight with longing, wanting a pair of lips on it, of any kind, desperate to thrust inside a warm moistness, so my cum could spill out. I knew how he felt, and how horny he must have been, watching me dream of Wendy, fucking and sucking her in my dreams.

My thoughts started to wander down paths they'd never been. I watched my fingers, not quite automatically rubbing his shaft, feeling the thickness of his cock on my fingertips and palm, the swollen head on one end and the pubic hair at the other, brushing my fist as I jacked him off.