Pleasure Spots: Anal Education

After their lunch meeting had ended, Vanessa went back to her office where she had emails to answer, phone calls to make, as well as other miscellaneous tasks that come with being an agent.

All the while, she had been told to expect an email from the doctor regarding the game plan. That email was all she could think about as she continued her daily business.

Finally, before she was about to head home, an email from Morgan came.

It was entitled: Your anal virginity

Hi Vanessa,

Here's the approach I think the three of us should have. It's only a suggestion, but I think this strategy would work best. Let me know if you'd like to make any changes!

love,

Morgan

- Let Keith read my chapter on anal deflowering beforehand.

- Cleanliness is very important, so I suggest you take a quick shower and clean yourself 'down there.'

- Wear something light. I recommend a negligee, nothing underneath for easy access.

- Keith and I will also dress nicely, though less revealing, as our nudity is not important.

- We'll do this in your bedroom. The decor must be romantic and sweet. Leave that to me! Perfect for your anniversary night!

- I will 'host' this event.

- I will bring a variety of sex toys, lubricants, and oils. We'll work slowly.

- Keith, obviously, will be the one screwing your ass. That will be the grand finale.

- I'm open to 'fluffing' Keith, but I don't want to overstep my bounds. So we'll see how it goes.

- Forward this email to Keith to let him know our plans.

- We'll do this 10 pm on your anniversary night, to close the day with a bang. I hope that time is okay, if not, we can change things.

- And do you mind if I take notes for my book? I always have tons of thoughts during these sessions, and I don't want to lose them. It's just what I need to finish off my book with a true story.

Let me know!

The email made Vanessa smile, especially because of how specific it was. That doctor knew her stuff and had done this so many times, she was practically nonchalant about it.

She sat at her desk thinking for a long moment. Hell yes, she was coming around to this. But the detail? Details, details, details...

A simple click and she typed her reply:

Sounds like a plan Morgan!

You're the doctor, so you know best. I agree with your ideas. Also, go ahead and take notes. This is for your book, after all. Oh, the things I'd do for my clients. I should get paid more as your agent, but then again, this might be payment enough.

Finally, regarding Keith and 'fluffing,' go ahead. I know he won't mind. It might even be kind of hot for me to watch. Besides, even though you'd be looking into my ass and lubricating it, I'm still too modest to let you watch me suck Keith's cock. Weird, right? So go ahead and do that for me.

I'll forward all this to Keith before I change my mind.

love,

Vanessa

Once that email was sent, she forwarded everything to her husband, who was still at work. She smiled naughtily to herself, imagining Keith getting a hard-on at his job while checking his messages. She imagined him having to do something while trying to hide the bulge in his pants, knowing that he'd finally be able to claim his wife's ass, and that Morgan will suck his dick.

Was that a fantasy of his? Morgan sucking his dick? She wondered. In the end, Dr. Latrell was hot, so of course Keith had fantasized about it.

She leaned back and wondered how this craziness all came about. Her eyes wandered back to her bookshelf of prized literature, then she realized, this is all part of the job, isn't it?

***

As expected, the anniversary dinner went well. Keith had made reservations for a fancy, overpriced restaurant, and Vanessa was treated like a princess. She couldn't remember the last time Keith had smiled so much and was upbeat about everything. He even gushed over some of the dishes that were underwhelming and overpriced. Vanessa had to wonder if he was just excited over the prospect of claiming her ass for the first time in front of a hot sex therapist.

Maybe he had to keep her in a great mood so she wouldn't change her mind about it. But, she didn't want to bring that up, and maybe, who knows, maybe Keith was just in a great mood because he loved her so much. Oh, who was she kidding. Of course anal sex was on his mind! It was something new, taboo, and forbidden.

Now that it was past 10, Vanessa looked at her reflection in the bathroom mirror. She was dressed in a sexy red negligee, which was mostly see-through, but covered her private parts. She was totally naked underneath and enjoyed the feeling of the soft fabric against her soft skin.

For an anniversary night like this, filled with romance and sexual adventure, she needed to look her best. No, extraordinary! She gave her hair another toss with her hands. She touched up her makeup so she'd have a classy, yet pornstar-ish look about her. It was a huge departure from her normal look in the office, yet that's what made it so fun, right?

A deep breath for extra confidence and she felt she was ready for this endeavor. Morgan had already arrived and was waiting in the bedroom along with Keith.

She opened the door and stepped into her bedroom, and there they were: Keith was still dressed nicely in the outfit he wore for dinner. Morgan wore a sleek black dress and was barefoot on the carpet, wearing those same trademark black framed glasses.

Both of them looked so pleased to see Vanessa, admiring her sexy appearance in that small red negligee. The room was done up nicely and there were even candles lit and rose petals laid around. There were also three glasses of champagne next to the variety of small sex toys and lubricants.

"You look lovely," Morgan grinned.

Keith looked excited at this new vision of his wife, as he also expressed the pleasure of what he was seeing. After all, it wasn't very often that Vanessa would dress up like this, with that potent makeup and lingerie combination. As open as she could be sexually, this wasn't necessarily her style. But on a night like tonight? A major exception was made.

"Thank you both," Vanessa replied, then playfully twirling herself around to model her negligee.

It was well-known that she took ballet in her youth, and she was glad that she still had the moves for it. Unfortunately, she twirled a little too hard, and the bottom of the negligee breezed upwards, giving a premature glimpse of her shaved pussy and nice butt. She quickly fixed her outfit and they all shared a laugh.

Morgan took the tray of champagne and handed one each to the married couple, and one for herself. It was time for a quick toast.

"To a one year anniversary," Morgan said, holding up her glass. "To my new book. And some hot anal sex."

They laughed again to ease the nerves as they also consumed their drinks. Once that little bit of celebration was out of the way, it was time for business.

Morgan sat comfortably on a chair, in a highly seductive manner, while the married couple sat on the bed, listening to every word. The doctor started with some introductory notes on the matter, which came from years of working with clients, giving seminars, and writing for various outlets.

"When having anal sex, two things are very important," Morgan explained professionally. "Starting at a slow pace, and using the right amount of lubrication. The anus is a dry area, unlike the vagina, and needs delicate treatment. Relaxation is key. Arousal makes things even better. Above all else, take things slow. Step by step. Before you know it, you'll no longer be an anal virgin."

The couple gave each other an adventurous look, like they were ready for anything.

"Now, as for your exhibitionist fantasy," Morgan said to Vanessa. "I want Keith to eat your pussy while I watch. This should get your blood flowing and set you in the right mood."

When a stunned Vanessa turned to her husband again, she saw that he was nothing but smiles. How else would a man in his position react?

Instead of giving an awkward reply or making a fuss about it, Vanessa simplified things. She spread her legs slowly and pulled the bottom of her negligee up. With her pussy revealed, the mood in the bedroom changed-- for the better.

Keith kissed her on the cheek and smiled, "I love you, baby."

Then he sank to his knees to serve that pussy he knew all too well. Vanessa moaned as her husband went to work. She had become accustomed to this pleasurable sensation, as Keith knew exactly how to please her. She had told him all of her preferences and sensitive spots.

But what made this particularly raunchy was that Morgan was looking her straight in the eyes, with a big grin and her glasses tilted forward.

Neither of them broke eye contact. Vanessa knew what this was about. The doctor was pushing the boundaries and had wanted Vanessa to be brave about this. To enjoy this exhibitionist feeling in the bedroom. So Vanessa just stared right back at the doctor, seeing who would break first, but neither of them did.

That was, until Keith plunged his tongue deep into her pussy, causing Vanessa to tilt her head back and moan.

"God, you're going to make me cum," she whispered.

The exhibitionist feeling of her client watching her, and her husband's oral technique was all too much.

"Go ahead," Morgan said. "I want to see how you orgasm, your facial expressions and all. An orgasm would be a great way to start your anal training."

As if on command, an orgasmic sensation rushed through Vanessa and she came in her husband's mouth. It was a short and fast one. Not too powerful, which was a good thing, as she needed energy for the anal fucking. But it felt delightful and got her blood flowing.

She relaxed and briefly laid on the bed, while her husband pulled his mouth away.

"Bravo," Morgan said, standing up to approach the couple. "You're becoming uninhibited. I like seeing you like this."

"Apparently you're about to see a lot more."

"You're right. Turn around. Lay on your stomach. Keep your feet on the floor."

Vanessa gave a playful look which read, I better be in good hands, before turning over to follow instructions. She laid on her stomach with her feet off the bed. A perfect position for anal fucking.

Both the doctor and her husband got behind her. Then she felt someone hike her negligee up and toss it over her back, leaving her butt exposed.

"Cute bottom," Morgan said, rubbing her hands over it. "You have a nice ass, as I suspected. Now spread 'em."

Vanessa spread herself, knowing that both of them had a clear view of her wet pussy by now, and most importantly of all-- her little brown anus.

The view to her ass was made clearer when Morgan spread each of the butt cheeks apart, revealing the anus in its entirety. It was held like that for a while so they could have a good look. Vanessa felt embarrassed by this.

Morgan said to the couple, "I like to start with stimulating the outer area of the anus, working my way in. I like using my three touches; fingers, lips, tongue."

Fingers? Lips? Tongue? Vanessa's eyes widened in anticipation for what this might feel like in her little hole, since it was her friend/client doing this for her, in front of her husband! What a combination.

A moment later, Vanessa's curiosity was swept away and she felt the real thing. She felt her outer anus being rubbed by Morgan's soft fingers. The fingers twirled around gently before making their way to the middle, rubbing all the lines that surrounded the anus.

"Looks clean enough," Morgan said during the finger inspection.

That was when the doctor stuck her tongue out and licked the outer area of Vanessa's hole, before licking across the anus, feeling all the lines. The sensation made Vanessa clench and turn wide eyed. How delightful this felt. So ticklish and awkward. There was no doubt in her mind that she'd be asking her husband for this on a regular basis, and maybe she'd return the favor for him too.

She made a squeaking noise with her mouth the moment that tongue slipped inside of her tight hole. The tongue swirled around, making Vanessa smile. She nearly frowned when the tongue pulled out.

"Next comes the lubrication," Morgan said to Keith. "This is fairly simple. There are various kinds of lube, including oils, silicone based lube, and maybe even saliva. Tonight, we'll stick with traditional anal lube. Watch how I apply it, it's simple."

Morgan opened the container of lube and held it with one hand, while using her other hand to pull a butt cheek aside. With the anus partially spread, Morgan squeezed the container and coated the anus with lube.

The sex therapist explained, "This is like marinating meat. Rub, rub, rub. The outer part needs lube because that's where it needs to open. It also needs to go inside where all the fucking will occur. The rectal canal is a dry place. So handle it with love."

With that, Morgan plunged a finger inside of the ass, making Vanessa squirm in the process. Then two fingers, which made Vanessa gasp. The fingers probed around, going as far in as possible, coating that delicate rectal canal.

Then the fingers slipped out.

"Next," Morgan said. "A thin anal dildo is a good start, because it's slender and smooth. It's a great step towards full-on anal sex."

The sex therapist picked up a flesh colored thin dildo, and pressed it against the tip of the anus. With a push, it slipped inside the lubed hole, struggling to make its way inside.

Vanessa relished the feeling of fullness inside of her. It was something her butt had never felt before; a solid object slowly working its way inside of her canal, then being held there. It was held there for several seconds, allowing her rectum to accommodate the feeling of something that shape being inserted there.

She rested her face on the soft bed sheet, while listening to her husband converse with the sex therapist. They were talking about anal stretching and lubrication techniques. No doubt, this would be happening again. Her husband sounded like an intrigued college student with the questions he was asking, and the attention he paid with each response he got. Yes...mmm hmmm...got it...interesting... At least she knew she'd be in good hands, with a husband as smart as hers.

"How does that feel Vanessa?" Morgan asked.

"Like there's a sex toy in my butt," Vanessa curtly replied.

"Excellent. By the tone in your voice, you don't seem to be in any pain. I think we're ready to begin the anal fucking now."

When the thin anal dildo was pulled out of her ass, Vanessa felt a strange sensation. There was a hollowness in her ass, a gaping feeling, and she could feel a stream of air flowing inside. How very odd, indeed. A totally new sensation.

"Keith, pants off," Morgan ordered. "Get naked from the waist down, big boy."

Vanessa's interest was immediately piqued. She needed to see how this would play out. She turned her head around, while her ass remained in the same position, so she could see what they were up to.

Her husband was in the process of removing everything from the waist down, and the sex therapist was on her knees watching attentively.

When he was done, he stood there with his cock almost fully erect. If this was pure vaginal sex, that cock would be ready for immediate action. But this was anal sex, and he needed to be raging.

"Vanessa, do you mind?" Morgan asked, as they looked at each other.

The sex therapist used her hand to gesture at that cock, while still looking at Vanessa, politely asking for permission. Keith, meanwhile, did everything he could to suppress a bashful smile. He was like a virgin who had just seen a pair of breasts for the very first time. It was that kind of mischievous look.

"Go right ahead," Vanessa said. "But only what's necessary."

"Got it."

While Vanessa kept her head turned back at their direction, she watched as the sex therapist took that cock by the shaft and devoured it with her mouth. Her head quickly bobbed at lightening speed. Vanessa knew this technique from Morgan's latest manuscript, but actually seeing Morgan perform in front of her, it was a sight to behold...

This woman was a sexual goddess. A master at sucking cock. Vanessa made a mental note to ask for personal training later.

As quickly as this began, it ended just as fast. Morgan pulled her mouth away, leaving a trail of saliva hanging from her chin, which she immediately wiped way. Keith, meanwhile, was breathing heavy.

At the very least, his cock was extra lubed from Morgan's saliva.

"Now it's time to get into position," Morgan said, speaking like a porn director, guiding Keith into place.

She continued, "Remember. This is nothing like porn. You can't just go to town on her ass. This is real life. You must be slow and delicate. Communication is key. Read your wife's body language."

The sex therapist spread Vanessa's butt cheeks wide open, spreading that lubed asshole. Keith did his part and pressed the tip of his raging hard cock against his wife's asshole.

"Vanessa, this is the toughest part," Morgan said. "Relax the best you can. Just relax. If you feel any pain or discomfort, let us know."

"It's uncomfortable right now," Vanessa joked, as the tip of her husband's erection had penetrated her anus.

Morgan rubbed her friend's butt. "Poor girl. This level of pain and discomfort, you can handle. It will all be worth it. I promise."

The sex therapist continued coaching Keith, who slid his penetrating cock further into Vanessa's asshole. She did her best to relax. She fought with all her might not to clench onto the bed sheet. She simply let it happen. She savored the feeling of her asshole being stretched, inch by inch, to what felt like its full capacity. Thank goodness for all that lube and preparation.

She could feel herself engulfing that cock. Devouring him. It was a strange level of intimacy, that his sex would be stuffed inside of her taboo hole. And if she were honest with herself, she found the feeling (both physical and mental) to be overwhelming, and quite frankly, it was really hot.

As the sex therapist instructed, Keith held position as his cock was buried all the way inside her rectum. It was a feeling she couldn't get used to, but then again, a person isn't supposed to get used to this. What she felt was close enough. She was relaxed as she'd ever be, under this circumstance.

"Move very, very slowly," Morgan instructed. "Fast movements will be painful, and could potentially damage the sensitive flesh of your wife's anus or rectum. This takes time. Again, examine your wife's body movements. She'll let you know if it's hurting, or if it's pleasurable."

Vanessa trusted her husband more than anyone else in the world. She knew that he knew all of her body movements; her desires, weaknesses, and strengths.

That assumption proved correct as Keith worked his cock slowly, gripping his hands along her waist, feeling for any reaction she may have. The cock slowly pulled back, until it felt like it was going to be pulled out, leaving a gaping feeling along the way, before slowing pushing back in to fill her rectum once more.

It was an intense feeling which took her breath away. She released a loud gasp as her anal virginity slipped way.

"So far, so good," Morgan said playfully. "Yes, keep this up Keith. As for you, Vanessa, let us know if there's any pain."

"It feels...good..."

Morgan ran her fingers through Vanessa's hair. "Sweet girl. You're a natural. Enjoy the pleasure."

The sex therapist moved away and let Keith take control of the situation. Each of them followed their instructions. Keith went slow, slow, slow, gauging his wife's reaction as he gradually worked up in speed. Vanessa did her best to relax her anus and rectal muscles so she could be properly fucked.