Ruth and Greg Go to 'Plan R'

The three of us met for coffee in the student union on Saturday. Greg probably needed as much calming as Shelley. In my talk with him an hour earlier, he may have been equal parts excited, scared, and freaked out about what seemed like sexual deviance. In the coffee talk, we were cordial and exchanged a little ice-breaking personal information. Shelley was a junior, majoring in mechanical engineering, so we'd probably never cross paths academically. She seemed to relax as we talked, and in time she was the one who said, "Well, I'm ready if you are."

Greg still had his room to himself. His roommate had pledged a frat, and the Housing Office hadn't yet moved in someone else. He was therefore able to orchestrate the event, and to his credit he had worked out a way to make this respectful and unthreatening for Shelley, while at the same time not presenting himself as her lover. He showed her his phone, and kept her watching while he put it in a desk drawer. He kept the lights off, and the blinds were down, so the room was about half-lit from the cloudy afternoon outside. He invited her to use the bathroom (which, in this dorm, he had to himself), and asked that while there she remove her bra.

When she emerged, he had her sit on a chair next to a bed, facing away. He sat on the edge of the bed, facing her back. I sat on the other bed, to do and say nothing unless requested. Still fully dressed, he said in a normal voice, "I'm going to reach inside your blouse." She nodded. He lifted the hem from the waistband and put his hands around her waist. She inhaled sharply when his hands touched her breasts, but then she added, "Go ahead."

I couldn't see much, but I could tell she was enjoying it. Now and then Greg asked what she liked, and what felt good. She told him a few things, her words getting long and dreamlike. When he asked if she wanted to use her hands too, she said, "No, this is nice, just you."

After she started moaning, Greg picked up a pillow and moved to kneel in front of her, saying, "Are you okay taking off your blouse?"

"Yeah!" she said, almost yanking at the buttons, then hauling it over her head and tossing it aside. "Please kiss them!"

Now I could see that, while her breasts were small, they extended out from her rib cage enough to present variable surfaces and movable bulk, and they were set close together. Her nipples and aureoles were about as big as mine. In that light, though, I could barely see them.

Greg set his hands along her sides, gently bringing her breasts together and holding them steady, and put his face on her nipples.

She gave a shuddering gasp, head jerking back.

And for all of my belief in the value and importance of this activity, rage flared through me. I had never been this angry before in my life! I wanted to chase her away, make her run through the quad with her little naked boobs jouncing, and I wanted him to spend forever making it up to me, especially to the breasts that now yearned for his treatments. At the same time, I was thrilled by her thrills, and proud of the guy who, no matter how freaked out he was by this, had really thought long and (ahem) hard about how to do this with a stranger.

Greg took a few moments during the several minutes of his efforts to tell her, "Guide me however you want," and "Let me know if I should change this," and "Would you like to finish with me?" (To which she wailed "Oh, yeah, if I can!") Then, "Just let me know. I'm taking off my pants," and "When you're ready, I'll lie on my back." (He disrobed his bottom half with one hand, which I remembered him doing the first time he and I had fucked.) Wicked genius that he is, Greg timed these speeches to keep her edged, at the brink of cumming, and each new round of breast love took her even higher.

I suddenly realized that I was finger fucking myself. I yanked my hand free, even as my nipples demanded rougher treatment.

"Now!" she yelped. "What do I do?"

As he moved to the bed and spread lube on his groin, he said, "Just lie on your stomach and bring your breasts around my prick, which will be up against my gut. Rub them up and down along it, while I fondle them." How could his voice be so calm and reassuring?

Shelley was mouth-breathing when she set her torso on Greg's crotch. He continued to pleasure her actively, fingering her nips and pressing his palms at the sides of her breasts as she rolled her chest along his upturned putz. This put her breasts on and along the most sensitive parts of his penis, and also brought them into some contact with his balls. Small as they were, her boobs' warmth and soft/firm combination fucked his glans, semen duct, and undershaft. What she had, and did, was enough to send any tit lover through the roof.

His squeezing and fingering, and (she said later) tickling from his pubic hair, sent her over the edge. As she keened, with her eyes squinched shut, he let himself go, adding his spooj to the lube slicking his belly.

She was a long time catching her breath. I was struck by their opposite half-nakedness, Shelley still in jeans and Greg still in a sweater.

Finally she said, "You good?"

"Yeah," he gasped.

"So I don't have to lick it?"

***

While Shelley was in the bathroom cleaning up, I walked over and leaned down at my fuck buddy. Quietly I said, "Plan R," with my voice unsteady.

He nodded, chuckling. I wanted to slap him, but there were a lot of irrational impulses going through me right then, including to do the licking Shelley had declined. We had worked out in advance what, if anything, we'd do after this session. We considered several possibilities. Under Plan R, we would fuck like rabbits as soon as Shelley was gone.

I pulled up the lower half of the bedspread to cover his display of genitals and goo. Shelley emerged from the bathroom and said, "Gosh, that was great, thanks so much!" She took a step towards the bed, then stopped, looking uncertainly at me. To Greg, "Can I kiss you?"

He smiled, propping up on one elbow. "As a friend."

Again she looked at me. I nodded, I think smiling, though who knows if she saw it, the room was still half-lit.

It was a chaste kiss on the lips. After which Greg said, "Anybody can do that for you. Male or female."

That last sentence took her aback. Maybe that helped delay her realization that Greg was giving her a brushoff.

She gave me a light-touch lean-in hug and said, "Thanks, what a great friend you are!" She glanced at Greg, and then said to me, smirking, "Enjoy the main event." And so she exited.

Nothing studious or casual about what happened next. He showed that he was just as agitated for me as I'd been for him. First, a long energetic pussyfuck, during which I was already cumming when he suddenly hard-sucked my boobs and the condom flexed, and somehow I came bigger. Second, a shower in which we both came from general groping. Third, breast love and titfucking, finishing in the position Shelley had used, the first time we'd done it that way. Fourth, a less intense shower. Fifth, cuddling that started calm but ended up as another pussyfuck. At some point during all that, we agreed that we needed to think about what this level of excitement said about our turn-ons. So much for my earlier plan to postpone going past his third orgasm in one session. He had four, two in my pussy, and they were after the one between Shelley's boobs.

I was sailing happily as he escorted me back to my dorm, with no negative feelings towards Greg or Shelley or anyone. Luv ya, World!

The next day, I could barely walk. I had learned something important about my body: How much is too much. Maybe I didn't have to ride his three fingers in the shower for so long, but it felt great at the time.

***

This is Greg again. I want to go on record stating that finding a different man for Ruth is much more difficult, and with many more downsides, than finding a different woman for me. How can we know how a man will respond, during and after a session with Ruth? None of our acquaintances on campus are close. They're all at or beyond the age of consent, but emotional maturity may not be complete in all cases, especially among males. Some guy who seems decent and unselfish, and shows no hostility towards women, might be entirely different when his pants drop and her breasts appear.

Even if I'm in the room while that tryst happens, I can't guarantee her safety. I've never been in a real, physical fight. All I could offer are quick fingers to 9-1-1.

Even if the guy understands and respects Ruth's boundaries, what he does after could be bad, if he blabs about this girl who let him fuck her tits. Ruth and I quasi-vetted each other for months, and were still worried about what would happen. There's been barely any vetting of other men.

This encounter is not the same as mine with Shelley, and I don't care if that assertion comes across as sexist. What happens if Shelley tells the world about me? Maybe I get a little embarrassed, and maybe some other women ask for similar treatment. Almost no downside for me, in the near or far future. That's just the way the world treats a man's sexual exploits. The way the world treats a woman's sexual exploits is to call her a slut. Even now, fifty-some years after the supposed sexual revolution. I am not going to let that kind of shadow exist on her reputation, even if she considers my thinking paternalistic and outmoded. She's my friend, and if I perceive potential harm to her, I'll try to prevent it, regardless of her dismissal of such harm.

I've made virtually no headway on finding a guy for Ruth to educate on breast love. I've tried. Since she pimped me to Shelley, it would theoretically be fair for me to pimp her to some guy. (Yes, Ruth, pimp is the proper term, and even if you don't want it posted I'll do it anyway. Have you figured out that I don't feel good about this?) I've started dating-related conversations with some guys I know, dorm neighbors and classmates and study partners. I've found potential red flags with all but two of these men. One of the remaining two has dated the same woman three times in the past month, and they might be on the brink of a relationship. The other guy is even more awkward socially than I was.

Ruth's response to my report on this was a suggestion that I bring Mr. Awkward to the Tuesday discussion group, so she can meet him and start her own data bank on him. Despite my exasperation, I told her I'd do that.

He'll be there. And, having gone on record with the diatribe above, I reserve the right to interfere with further developments, if there are any.

***

Welcome to further developments.

Let's call him Carlos. I know him because he's a sophomore majoring in economics, and at this level he and I (a business major) have two classes together. Ruth calls me a capitalist, and I've never denied it, but Carlos is more narrowly focused than I am. He's an acolyte of the late Milton Friedman. Fortunately, one way I can stop him from orating on the virtues of the free market (a topic on which I do not need to be a preached choir member) is to change the subject to women. He drops volume to hushed tones, lavishly praises feminine beauty (which he seems to attribute to every woman who ever lived), and wants to know everything about women with whom I'm acquainted. I have no first-hand knowledge of him ever having a conversation with a woman.

He's angular and scrawny, and has trouble achieving the state known as quiet body. He's bespectacled and has an overbite, but not buck teeth. His hair is pretty much like mine, black and straight and medium length.

The discussion at the bookish bar often touches on economic theory and practice. I got Carlos to promise that he would just listen, as a newcomer, and not stick in his Friedmanite oar, and in return I'd introduce him to a female friend of mine, so he could have the experience of conversing with her.

In public, Ruth is often sarcastic and a destroyer of weak arguments. To Carlos, she was gentle. I had found that he was interested in photography (more the tech side than the art), and Ruth had studied up enough to speak and listen on the subject. After the discussion group dispersed, Carlos and Ruth actually managed a few minutes of unforced conversation.

Ruth turned a corner with: "Is photography what you do for fun?"

Carlos glanced at me. I took this to mean that, for him, fun was studying and talking about his favorite brand of economics. I shook my head. Carlos looked at Ruth and said, "No." Then, after a few seconds of what might have been furious thought, he seemed to shrivel as he said. "I don't do this very much. Being with people."

This ended on some nice-to-meet-yous and see-you-here-again-next-weeks. Ruth later told me that she wouldn't rule him out, but worried that taking him as far as breast sex might do things to him that shouldn't be done to someone with so little confidence around others. She said that she'd continue trying to find a guy herself. I have to say, I felt a little threatened by this.

She also told me that one of her dorm neighbors badgered Shelley, and got from her a few words about her session with me. This woman, whom Ruth calls Meg, wants to meet me. I have to say, I felt a little boosted by this.

Ruth and I skipped the next Saturday while she menstruated. This condition, of course, need not interfere with breast sex, unless the woman just feels too crummy. That was the case, so we spent the whole weekend hitting the books. Probably good for our GPAs but, still, bummer.

The next Tuesday, however, it was clear that Carlos had done something. He was more poised. He chimed in during the big discussion, but only briefly, and with relevance to the topic at the time. Later, with Ruth and me, he asked about what we'd done the past week and described what he'd done, all under a heading of small life moments (hurrying back to get a forgotten book before class, enjoying a walk through fallen leaves).

Ruth and I shared a glance, and then she excused herself for a trip to the powder room. As soon as she was out of sight I told him, "You don't seem so nervous tonight."

He grinned. "Last week, you and Ruth were so nice to me, I thought I should try to up my sport on, mm..."

He tried to gesture out the next word. Before he could get there, I backtracked. "Up your game?"

"That's it," he said with a quick nod. "Up my game on being around other people. So I looked at some online resources. Sites about being comfortable around people, and making them comfortable around me. Some sites have bots that allow practice conversations. Then I started doing that with real people, here on campus." He laughed, nervously but not in dismay. "I may have made a fool of myself a few times. But most people have been nice. Also, surprised that I'd talk to them."

"Good for you," I said, smiling, and thinking that he might be a better alternative than someone Ruth recruited. But could he really deal with her putting a move on him?

When Ruth returned, the small talk resumed, with Carlos looking like each exchange was a major victory. Ruth got the discussion onto the topic of companionship, in the abstract. At first, this made Carlos retreat to shyness, although his curiosity about Ruth and me eventually brought him back. We gave him the public-consumption line about being close friends but not romantically involved.

Along about then I caught a glance from Ruth with an eye-move towards the restrooms. I thought, Seriously? Still, I got to my feet and said, "'Scuse me, this artisanal beer wants to become artisanal something-else." And off I went to the men's room, managing not to shake my head.

I gave them five minutes. When I returned, Carlos was waxing rhapsodic about the free market and she was letting it happen. (Something she'd never do with me, because close friends can kneecap each other's worldviews.) It was a minute or so later that Ruth supposedly became aware of the time, and said that she had to call it a night. Carlos accepted my saying that I'd walk her back to her dorm, and he departed by himself.

As we walked, I said, "And?"

"The three of us will meet in the student union on Saturday."

Stretching the vowel, I repeated, "And?"

"I offered to help him learn about female anatomy and pleasure. Within definite limits, and not as something he can pursue immediately with someone else."

"You're assuming he's a virgin?"

"Aren't you?"

I admitted, "That's become pretty clear in my conversations with him about women." I pressed on: "So you'll be boobs-out. What about him?"

"I'll decide at the time what else seems reasonable."

On to Saturday. I've never thought of myself as an actor, but in fact I created a sort of unthreatening breast-lover persona for myself with Shelley, and it seemed to help a lot. My role today was that of an upbeat friend of two people who would use my dorm room for amorous activity. I think I maintained the act, starting with when I told Carlos I'd be in the room with them, just to make sure there were no problems (without specifying what those problems might be). Carlos wasn't sure what to make of this, but I think he might have been even more nervous if he and Ruth were the only occupants.

Ruth gave him a few chances to beg off, right up to when she was sitting on the side of a bed, with her back slightly arched, and he was sitting in an armless chair facing her, knees-to-knees. Fear seemed to help him hold still.

"Tell me if you think you're getting too excited," Ruth said, and then she pulled her sweater off over her head. Unlike with Shelley, there was light in the room, showing clearly her opaque, light blue bra. As plain as it was, its construction (and hers) presented, above the fabric, her dramatic forward curves and a dark line of cleavage. Carlos inhaled sharply but mostly held still.

"Beautiful," he said. "Thank you."

She smiled. "You're welcome. Shall I continue?"

"Ohhhh yes please."

She reached behind, unhooked the bra, and slid it down her arms.

His head drew back, and his right leg twitched.

"Are you all right?"

He took a slow breath, and then another. Then he nodded.

She put her hands in her lap and spoke slowly. "Everyone, male or female, responds in a unique way to touches and other forms of contact. It happens that I really enjoy my breasts. This isn't true of all women."

He nodded, as if mesmerized. Lord knows, her boobs do that to me sometimes too.

"If you'd like to touch them," she said, "Put a hand, palm up, underneath each one, and cup them firmly. Enough to lift, but not squeeze." Slowly, arms trembling, he did that.

I'm going to gloss over a lot, because this took a really long time. Gotta say, though, that it worked. Ruth guided him through the feel of her breasts, the sensations in her nipples and aureoles. As time passed, he got accustomed and seemed less likely to have either a panic attack or a pants explosion. He finally stopped thanking her, after maybe her fourth request to stop.

Then Ruth took him through what could really arouse her. She kept advising him, but through heavy breathing. I had generally been bored, but now I was getting hot, mostly because she was.

She said, "Why don't you take off your pants and shorts? You'll be more comfortable." This took him a couple minutes, because he didn't want to lose contact with her. Been there, done that.

"Now," she said, half-gasping, "Please kiss my nipples, and lick all around them."

And this, along with her moving his hands around and making them squeeze her tit meat, got her to a shuddering orgasm.

I realized that this was the first time I had watched other people have sex, in the same place where I was. I was seated behind my desk, which blocked their view of most of me. I took down my pants and shorts, just to free my shlong. The head of the prick pushed up against the bottom of the center drawer.