Women Enjoying Naked Men Ch. 03

"And if they don't know it?" Taryn asked. "You see, that's exactly what I'm the most anxious about. This man who also teaches at the university is someone I've just begun dating, but he's definitely someone I'm interested in continuing to date. He's funny and intelligent, and he has a nice body — something I noticed the first time I saw him at the gym."

Reading the woman's continued expression of interest, Taryn pressed ahead: "I guess the first thing I want to learn about him is all the normal and exciting — wait, what's the term you use?" she asked the woman, but continued on after immediately remembering the discussion during the first workshop, "all the normal and exciting vanilla sex stuff that I know I'll always adore," she said, finishing the sentence. "I mean, if our relationship progresses and he's maybe THE ONE-" Taryn rolled her eyes at her own use of the cliché, "-well, I would not want to jeopardize that by blurting out I'm dying to use a strapon on his sexy ass and then be rejected, maybe even lose him because of what I said I want."

"Trust me," said the woman, "you are not a blurter."

The woman leaned toward Taryn, placing a hand lightly on her forearm.

"But you have a legitimate concern. I know of stories where just such an inquiry ended the relationship."

"So you see my dilemma," Taryn said.

"All too clearly. And I'll give you the same advice I give to anyone, male or female, about bringing this topic up. If you're with a compatible person and you've both discovered you're okay doing some other kinds of sexual play that might be considered not so vanilla, but not as adventuresome as strapon sex, then the natural progression in the relationship means it's probably okay to ask to peg or be pegged."

Taryn's blank expression begged for more explanation from the woman who was fast becoming her pegging mentor.

"Just imagine all the fun you'll have along the way before you ask this man to engage in strapon play," the woman said. "Remember the workshop conversation earlier about fingers during a blowjob as a perfect first step down the future pegging highway?"

"And what if during all that fun I fall deeper and deeper in love with him and then he dumps me because I've crossed some line that instantly splits us up?"

After a reluctant sigh, the woman took a pensive tone, chewing her lip for a moment before replying.

"It's a chance you have to take, is what I've decided," she said. "It happened to me once, and I hated it, but I realize now it was the best thing."

Taryn shifted in her seat, a brief wave of anxiety passing through her.

"But how sad would it be," the workshop leader continued, "if the person you love is also the person you have to hide an intense sexual desire from? How sad if he doesn't accept you and all the ways you want to play together?"

The woman leaned forward, lowering her voice to reassure Taryn this conversation, having taken such a private turn, would not be overheard. (The other workshop attendees were respecting the one-on-one discussion, thankfully.)

"If it doesn't hurt your partner — at least, doesn't hurt in a bad way," the woman said, smiling gently, "then your partner should at least be non-judgmental, even if he ultimately says he just doesn't want to get pegged. Then you know not to bring it up again and you have a choice: you can stay with him, knowing your pegging fantasies will always be just that, or you can decide you'll look for a friend with pegging benefits, or you can end the relationship and move on."

Taryn's crestfallen look was plain on her face. She looked down at her hands, clasped with nervous fingers interlaced, fidgeting.

"Please don't think I'm saying you have to give up! Goodness, no! You will have to decide if you're going to take the risk, but it's worth it. It is s-o-o-o-o worth it. After all, your handsome professor may at this very moment be at home, sliding a butt plug inside his sexy ass, and masturbating to fantasies of you doing him with your strapon."

The comment lightened the mood immediately, and Taryn grinned, hopeful optimism working its way back into her countenance.

Noticing a couple lingering a respectful distance away but obviously eager to speak with her, the workshop leader rose from her chair but leaned down to make one more comment before departing to talk to other of her fans. "Oh, when you have that discussion with your lucky professor, there's another option you'll have besides him saying yes and the two of you pegging your hearts out, him saying no and you staying but with pegging always just a fantasy, him saying no and you then trying to find a friend with pegging benefits, or you ending the relationship."

Taryn looked up from her seat inquisitively.

"You could get a referral _from_ a friend who _has_ a friend with pegging benefits."

With nothing more said, the woman left to mingle with the couple and then the other workshoppers.

_Huh?_

Was she implying she has a friend she occasionally pegs that she would introduce me to? Taryn wondered, a small ripple of excitement causing a slight flush across her collarbones.

_Is there some guy she knows who isn't a lover or a partner but who enjoys getting pegged and who himself isn't in a committed relationship?_

What the workshop leader's comment portended had Taryn's mind doing backflips:

A man to peg with no strings attached?

A nice guy willing to meet for a pegging encounter just because he liked it? (The assumption about the man made sense to Taryn: surely any friend with pegging benefits involved with the workshop leader — herself an intelligent, fun, grounded human being — would be a nice guy.)

True, their conversation had centered around her options if her relationship with the new man she was seeing evolved successfully to the point of a pegging conversation, but . . . what if-

_What if it were possible to practice-peg a guy BEFORE I do it with the man I'm in a relationship with?_ thought Taryn.

Holy freakin' shit!

The concept hit Taryn square in the solar plexus.

And then it slid right down to her pussy.

Damn!

The first workshop of the evening had included comments from the pegging expert about guys going to a pro for their initiation into pegging if it was impossible to find a woman who would do it or to convince a girlfriend or wife to engage in strapon play. The idea racing around Taryn's mind right now was a version of that, an idea she had never considered: It would be the woman — _her_ — being the one "going to a pro" for an initiation to strapon play.

The thought was delicious: the workshop leader (or _anybody!_) introducing her to a guy who liked to get pegged and who would enjoy bending over for Taryn and helping her learn the subtleties of man-fucking in a way no amount of practice with her male ass substitute mounted to a countertop or shower wall would ever allow.

That would be amazing! And knowing there was no relationship on the line, no worries about anything except learning how good it would feel to finally fuck a man with her strapon and learning first-hand with a naked guy the general guidelines for man-fucking — how fantastic would that be!

"Hands-on practice is always the best way to learn anything," Taryn recalled her aunt telling her once when she was teaching Taryn how to make a cherry pie.

_Auntie has no idea how much I agree with her advice right now_, Taryn thought, smiling to herself.

It was so-o-o-o-o important to her that the first time pegging her partner — knowing by then things would have progressed to the point that she really cared about him, about continuing the relationship — should be a fantastic experience for both of them. If she were good at it, and could guide him, urge him into positions that would all feel good but in different ways, then his first experience taking her strapon, and her first experience fucking him, would be much more likely to be a resounding success.

And that they would continue.

Practicing on a guy first, a man in whom she had no relationship interests other than him being her pegging sextoy and a guide from the male perspective about strapon play, had so many positives and only one negative.

How the hell could she get such a referral?

The workshop leader's last comment to her . . . did it mean she might actually . . .

Shaking her mind from its vice-like grip on the idea of somehow arranging a practice pegging session, Taryn gathered her purse and the book and walked briskly to the pegging merchandise display in the shop. She was eager to get one of the double-ended strapons the evening's speaker had identified as her personal favorite before that model was sold out.

It was going to be an intensely satisfying evening when she got back to her loft, Taryn knew.

Those pictures in the book . . .

A new strapon, this one built with the same ability to invade the tight recesses of an eager male asshole but also possessing the ability to stimulate her G-spot while she fucked the man who would be writhing in pleasure on the other end of the dildo.

Could she even wait through the second workshop before rushing home with her purchases?

Taryn was glad she did.

The sexy talk continued in the session after the break. Seated again in the back row, her bag of purchases now tucked underneath the chair along with her purse, Taryn eagerly listened to every discussion on every topic: the best way to ensure orgasms for both partners, more tips about toys and using them, excellent and detailed descriptions and explanations about the male anatomy and how to stimulate it (from anus to perineum to cock and balls and the holy grail of male arousal, the prostate), more information about positions and techniques.

One of her favorite topics was the psychology of strapon play. She had never considered what it might do to her perspective about sex, about gender roles, about expanding her sense of self and, importantly, allowing her partner to expand and accept his sense of himself.

But it made sense. Taryn remembered what it felt like the first time she had strapped into her dildo. Seeing her reflection in the bathroom mirror, the stout and unavoidable visual of an erect phallus protruding from her crotch, had felt empowering, different.

It had triggered some deeply atavistic, primal urge that must exist in both genders to thrust their hips, to seek a sexual coupling and enter the other — to unify somehow, at least physically, with another human being.

Such a feeling would surely be magnified during a strapon encounter.

What would that do to her mind, to how she considered the intimacy of sex? What would it mean for regular male-female interaction in her bedroom between her and her man after their initial strapon coupling?

"Men have told me how much they have to trust their partner to open up and surrender themselves to being penetrated," the workshop leader said during the evening's second session. "And that's easy to understand, right, ladies?" she asked, a wry smile crinkling the sides of her eyes slightly. "We women have had to trust our partners for our whole lives, but the mind trip of giving up control to your lover and letting _her_ fuck _you_ is something that can take a guy by surprise."

Taryn had never reflected on the male psychological perspective of getting fucked in the ass.

It had always been so very arousing, so exciting and powerfully erotic to think about doing a guy with her strapon, to see it in pictures and videos, to fantasize about it as she masturbated to orgasm, that she had not yet delved deeper than the pure sexiness of the act, the pure physical enjoyment and intensely satisfying orgasms the fantasy dependably produced.

"And so many women have told me their men are more, uhm, how should I say this?" the workshop leader mused during this part of the evening's second session. "Uh, I guess these women mean their men are more sensitive, more caring, more . . ." Pausing for a brief second, the woman then snapped her fingers and said, "More intimate! Women often report their men are more intimate with them after they've been the ones on the receiving end of penetrative sex."

Having read this on the woman's web site, it wasn't new information for Taryn, but hearing this side benefit of pegging a male partner described out loud somehow had a stronger impact than reading it.

_Damn! The incredibly erotic pleasure of strapon-fucking my guy AND the pleasure of more dreamy snuggling too?_

Could sexual perfection come wrapped up in a prettier bow?

Taryn was so-o-o-o-o glad she had come tonight.

She would come tonight at home, too. Probably multiple times, armed now with new pictures of strapon sex between a handsome couple, a new strapon dildo whose construction would let her experiment with G-spot stimulation while sliding the shaft of the toy into her pretend male asshole, and a new perspective on even more strapon sex benefits than just the crazysexyhot orgasm-inducing thrill of man-fucking.

A sort of follow-up to the first workshop involved some additional information about ensuring the man's comfort, especially if he's a pegging virgin. The evening's initial exploration of that topic intensely interested Taryn because she was so eager for everything to be fairy-tale perfect the first time she used her strapon. Assuming the guy might be a first-timer, all tips about techniques to make the act comfortable and intensely pleasurable for her partner were important to her.

But after the conversation with the evening's guest speaker during the break, Taryn listened with a slightly different perspective. The woman had said Taryn's practice set-up might mean her first pegging would probably be quite successful, even using a double-ender. That comment now made Taryn realize she might be comfortable enough with all the pegging motions that it could be easy to rush ahead during the act, over-eager for the orgasm she knew would be incredible the first time she pegged a man.

In the intense sexual arousal of seeing the shaft of her strapon poised at the entrance of a man's asshole, Taryn realized she would be sorely tempted to plunge into him in a single, rapid thrust in order to bury her dildo deep in his ass so she could immediately begin fucking him.

"It is so-o-o-o important, ladies," the workshop leader said at one point during the second session, "to go very, very slowly during the initial penetration with your strapon. Don't even think about using your strapon until after you've warmed him up and relaxed him in other ways."

_Keep talking_, thought Taryn, hopeful the woman would pass along multiple inventive ideas about playing with a naked man in prelude to fucking him.

"As I mentioned in the first session tonight, a gentle, slippery massage of his anus is always a nice warm-up," the woman said, tossing her hair with a slight neck twist before leaning forward on the love seat. "Might I now further suggest, ladies, that 'gentle and slippery' also apply as perfect adjectives for the kind of massage possible with your tongue?"

The woman had just punched another of Taryn's dying-to-do-it buttons, one of the buttons she didn't know existed before her introduction to the scientifically substantiated reality of female lust for hard male cocks and tight male buttocks.

Only after accepting the rightness and inevitability that sexually aroused men were supposed to stoke the fires of her own lust did Taryn allow even the thought that new and previously unthinkable ways of turning a guy on sexually would be a turn-on for her, too.

Coming to that realization created a welcoming acceptance that tonguing a man's asshole would get him crazy hot and would contribute to producing the wonderful visual of his hard, throbbing cock.

And seeing his hard, throbbing cock, she knew, would get her crazy hot, too.

She had added rimming to her pegging-related want-to-do-it list shortly after fully embracing the idea that sliding the shaft of a strapon cock deep inside a man's asshole was the most sexually arousing act she could imagine. Her fantasy-fuck of Darrian's ass right after she got her male masturbation sextoy only confirmed it: she found it incredibly arousing to imagine tonguing his asshole as he moaned and squirmed in her grasp.

"Don't even get me started on how exciting I find it when a guy moans as I tongue him," the woman continued. "Then, when he's adjusted to the sheer naughtiness and sexiness of what I'm doing to him, he always lets me know with his body that he's ready for the next stage of his strapon initiation."

It was another of those tease-'em-then-please-'em points in the pegging expert's delivery. She hesitated before continuing, smiling to let her audience know she would quickly reveal the next stage of male pegging readiness as a reward for their patience.

The proverbial pin-drop would have thundered throughout the room during the woman's pause.

"He relaxes his asshole and he pushes back, sending an urgent message that he wants my tongue deeper inside."

_Dammit_, thought Taryn, squirming as she drew in a breath, realizing the woman's commentary had again created one of those hold-your-breath-in-anticipation moments. _I guess there's no way the ad in the paper could have described what's happening here tonight, but it would have been nice to know ahead of time the talk was going to be pulled from my personal fantasies_, she thought.

She realized the ad could not have come with one of those parental advisory-type stickers: "Warning! Taryn Roberts' personal masturbatory fantasies of strapon man-fucking, cock-sucking, finger-in-asshole play, rimming, and naked-male-with-erection-on-display will be discussed. Plan on wearing extra-absorbent panties."

"This relaxation and invitation is maybe the most important thing to be sensitive to when you're about to push your strapon inside him, as well," the workshop leader said. "Remember the two sphincters we talked about in the first workshop?" the woman asked the group. "When you enter him the first time, you have to pause just after the tip of your strapon presses beyond that initial ring of muscle. Once you're at that point, you must stop and let him adjust."

This was truly expert advice!

"Recall your explorations with your finger. You've felt him open that first door as you massage his anus, but then you know what happens as you continue to slide deeper — you go through a second door before you're inside his warm, snug rectum."

Damn!

"The shaft of your strapon is a lot thicker than your finger, ladies, so you have to go slow, you must give him time to adjust. He must be ready and willing to open that second door, so just hold off on your eagerness to plow into him!"

Giggles rippled through the audience.

But Taryn realized this was incredibly important information in light of the pegging expert's suggestion that Taryn's pegging skills during her first man-fucking session might be fairly accomplished. Pushing through Door One and then immediately through Door Two would be so easy to do, so tempting.

She would be desperately horny in that moment to fuck the man!

Now Taryn knew she must rein in her desperation in that critically important moment — it was vital for the man's comfort and arousal.

After more informative talk about successful male virgin-fucking, a middle-aged man in the audience, someone who was obviously there with his wife, said, "The sight of my wife strapped into our favorite toy is just about the sexiest thing I have ever seen." His statement prefaced a question: "She seems a little embarrassed to let me look at her that way, though. We've talked about it, and she knows I like to see her like that, but there's still some kind of shyness that stands in her way."

"You are a lucky woman," the workshop leader said to the man's wife. The compliment brought a small smile from the woman everyone now knew was embarrassed by having her husband gaze at her while wearing their favorite strapon dildo.