Our Friend, Anne

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A longtime friend kindles a new intimacy with a couple.
4.3k words
4.71
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Part 1 of the 3 part series

Updated 06/09/2023
Created 06/15/2018
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"Anne is thinking of visiting for a weekend."

My wife Jill's voice ripped me away from the game I was playing intently on my phone. Anne was our longtime friend, and my wife's best friend.

We had been part of a group of young people that met through our careers and stayed close over the years. But while most of us had paired off, had kids, and settled down, Anne had remained single. Eventually she had grown frustrated with her bosses and the local dating scene, and moved to the South for a better job and to be closer to family.

"That's great! You two should take some girl time to catch up. I'll watch the kids. Let me know if I can do anything else."

"That's a nice thought. I'll have to find a way to return the favor." She walked over and gave me a kiss and a small smile.

I smiled too. Though my thoughts about Anne over the years hadn't always the purest, I knew nothing would ever come of it. But at least the two of them reconnecting would put Jill in a good mood. And that tended to work out well for me. I just had no idea how well.

---

"Hi guys!"

Anne emerged from the airport and quickly navigated the crowded sidewalk to greet us - Jill, myself, and our two girls. The kids loved their "Aunt Anne" and had made a sign welcoming her back to the city.

Anne came from an Italian family and reflected all the best features of her Mediterranean heritage. Dark hair that shined, almond shaped eyes that pulled you in, gorgeous legs, and a rack that begged for attention. She worked out regularly and was a fanatic for Latin dancing.

Each of us got a hug in turn. In my case, it lasted a little longer and was a little tight for a friend. "Hi Jack," she said softly as she pulled me in close. It was quite more of a greeting than I was expecting.

As we disengaged I snuck a quick look at my wife who had definitely noted the interaction but did not look displeased. I grabbed Anne's luggage and we made our way to the car.

The day passed quickly as Anne and Jill chatted, played with girls, and we all took the dog for a walk. I tried hard to be the good husband, participating in the conversation but not dominating it. I heard about challenges at Anne's new work, and the oversupply of shitty guys in her new hometown. Nothing changes I guess. As my wife put it, "she has a taste for dog shit when it comes to men." Both Jill and I wanted her to be happy, and it was a sad to hear the change in locale hadn't brought much improvement.

As the day began to become evening, I asked the two what they were planning for the evening.

"Oh, I don't know if I am up for going out. What do you think about ordering some food for delivery?" my wife responded, turning to Anne.

"That's crazy," I cut in. "You two haven't seen each other in forever. You should go out to someplace nice, have a bottle of wine, and really catch up." It seemed only right. My wife was a homebody until you got her out on the town with good company. And for her, a nice glass of red was like high-octane engine fuel when it came to the bedroom. So that might turn out nice for me too.

"Yeah, come on Jill," added Anne. This was a practiced routine for the two of us from the old days, and it was nice to know that even after all the years we still knew our parts.

"Ok, there is that new seafood place I've wanted to try," Jill relented. Anne and I exchanged a knowing smile. "But we're taking a Lyft so I can have a drink."

"Great, it's settled," I added.

The next hour was a flurry as I pulled together food for the kids and the two ladies "made themselves presentable" for the evening.

"Wow," I commented as they came out, "You both look amazing."

"Thanks honey, see you later!" my wife said as they headed out the door.

A wrestling/tickle match, bath, stories, and bedtime routine later, I was left sitting on the couch wondering when they would get back.

I didn't have to wait long. My phone light up with a text from Jill.

"Heading home soon. Hope u r still up."

"Of course," I replied. "Did u guys have a good time?"

"It was great. TY, u r such a good husband. I don't appreciate it enough."

"My pleasure. No need to thank me."

"Awwwwwww!" She might be a little tipsy, I thought. "I do! Anne's last guy was a selfish fuck who never cared if she was satisfied. WTF!"

This was certainly alcohol-induced texting. I chose my words carefully.

"That's too bad. She deserves better."

"Damn right. If only we knew someone up to the task."

There was a long pause. I wondered if they were paying, or heading home -- or maybe she'd just gone back to talking to Anne.

Then I saw that ... appear on my screen.

"In our ride, heading back. We think Anne should see how u treat me right."

The "We" exploded off the screen like a gunshot and my cock twitched. While I thought she had been having a private conversation with me, she had been having the same conversation with Anne.

"O.k. sounds good. What were you thinking?" I didn't want to overplay my hand.

"Get the coconut oil, roll a joint, and get set up in the guest bedroom. We'll be home soon."

If the previous text had been an explosion, this one was like an atomic bomb.

The joint was self-explanatory. Back in the day, the three of us had been the smoking buddies in the group. But the coconut oil was something else.

After twenty years together, I've made it a point to keep things new and interesting in the bedroom. A while ago I came across a Literotica article on Yoni (vaginal) massages. It sounded a little bizarre, a relaxation technique that brought on intense orgasms. But Jill agreed to try it and it worked. Like really worked. Lots of lubrication was key and that is how coconut oil became part of our sex life.

Not wanting to do anything to mess up this moment, I texted "Ok, on it."

"Good, and hurry we'll be there soon."

I flew into whirlwind -- making the necessary preparations. I had just finished when I heard the ladies coming up the front porch. They quickly made their way to the guest bedroom.

"Hi honey!" Jill bounded in, with Anne right behind -- both wearing big grins that showed nervous excitement smoothed over by the vino.

We hugged and I took the chance to embrace Jill against my body. After two decades, my desire for my wife remained the same.

I smelled her curly, brown locks. I felt her grapefruit breasts pressed against me, raspberry-sized nipples aroused. And I ran my hands down her back, coming to stroke her butt as we kissed.

I glanced over to Anne, worried she might be uncomfortable or embarrassed. But was surprised when my eyes met ones filled with excitement.

After Jill and I parted, Anne came over and hugged me as well. Her straight brunette bangs broke apart to reveal those enchanting brown eyes. As we stood there, hip-to-hip, she leaned back her head and shoulders, looked into my eyes and said, "I'm so looking forward to this Jack."

She smiled, closed her eyes, and then kissed me lightly on the lips. She withdrew, crossing to sit on the chair in the room. My wife already seated on the bed, sparked the joint as I joined her in a reclined position.

We passed the joint, as we had done before many times before in years passed, and talked about their dinner and the day. A tension began to build as the joint paused our encounter, creating anticipation of what was to come.

As it approached becoming a roach, Jill declared "I'm good" and snuffed it in the ashtray. In the past, she would have offered it around first -- but it was clear to me she was focused on other things.

Without a word, my wife rose and began peeling off clothes. Like all good massages, this one is best experienced naked.

"If it's ok, I want to have Anne watch from the chair," she asked me.

I nodded and began to get the coconut oil. I turned as she dropped her underwear and bra to the floor revealing her naked self.

I took a second to enjoy her bare breasts and closely trimmed bush, revealing the clear contours of her pussy lips with a hint of her clit already peeking out. I couldn't remember the last time I'd see her that aroused when she first undressed.

She lied down, face first on the bed. I began working her body at the head and shoulders, looking for kinks and focusing on the spots I know she keeps her tension.

It was a little funny. Anne and myself still fully clothed, as my hands worked on my naked wife. Anne and I made eye contact as I continued down Jill's shoulders to her arms, and both of us smiled again. A smile that shared an understanding that Jill enjoying this experience was the key if we were to truly enjoy this experience.

I continued my work, applying coconut oil as I went. The lower back, the inner thighs, the buttocks and anus -- a nice thing about this massage being it can touch the erogenous zones a commercial masseuse does not.

After the legs, she rolled over and I began working on the chest, breasts, and tummy. Observing her closely, I saw her becoming relaxed and ready to accept the vaginal massage. But it is also a little different with a third person watching. It was also the point where I got naked.

I began to undress as Jill lifted her knees to create a relaxed pose with her feet still resting on the bed. As I finished stripping down my hard on came free, pointing away from my body at a 90-degree angle. I sat between Jill's spread legs, and began to gently stroke around the outer lips of her labia with the coconut oil.

Looking over, I discovered that Anne had also chosen this opportunity to get naked as well. She was already seated, so I could only see her naked breasts, standing out from her body against gravity and narrowing down to conic, dimpled tips. And from my angle I could see no pubic hair below a taunt tummy.

I refocused on my work, applying coconut oil in large amounts to ensure a smooth touch as I worked the outer and then inner folds of the outer labia, before beginning to gradually work around the base of the inner labia and the vaginal opening.

After a few minutes and establishing a calming, deliberate pace, I felt Jill began to truly relax in spite of Anna's presence. Gradually she also showed increased arousal as the tissues began to extend and swell between my fingers.

I continued my work, beginning to stroke and knead the clit through the labia, bringing her close to orgasm -- even as she worked to keep the calm, deep breathing of massage.

I turned to see what Anne was doing and caught her playing with herself. With her legs spread, I could see she has a narrow rectangle of pubic hair directly above her bare pussy lips.

"Hey, wait your turn or you'll spoil it," I admonished her.

"Ok, but I can't see anything," she replied.

"Honey, would you be ok with Anne coming over here on the bed to get a better look?" I asked.

"Uh-huhhhhhh," Jill groaned her assent and as I switched my fingers' focus from her clit to her vaginal entry and began carefully, slowing rubbing every centimeter inside her.

I felt a shift in the weight of the bed and looked over to see Anne had lain herself down lengthwise, propped up on an elbow to get a good look at my fingers working my wife's cunt.

The fingers of one hand worked their way around to the parts of the aroused clitoris accessible inside. I began to slowly stroke them, using the fingers of my other hand to rub and gently tug her clit through the protective shield of her labia.

Her breathing intensified, as did Anne's next to me, her hot breath now and again blowing across my ever-stiff cock.

Jill began emitting a slow, deep moan and then I felt it. Her legs locked and her pelvis elevated as the climax hit her -- literally lifting her off the bed for a good 30 seconds before the intensity subsided and she slowly descended, body splaying out flat on the mattress.

As this orgasm began to hit, I felt Anne's hand reach out and close around my cock, beginning to furiously stroke it. Almost as if being denied access to her own honey pot, she needed to pursue someone's release during the intensity of the moment.

As Jill returned to Earth, unlocking her knees and dropping her legs down the mattress, Anne's arm and hand were caught underneath - revealing our extracurricular activities during the orgasm. Jill smiled and said, "I'm glad you thought that was hot. I did too." She laid her head back down to catch her breath. "Your turn with him, Anne."

Collecting myself, I rose from the bed and stood next to Anne as she lay out face down. Her gorgeous ass shaped like a heart was presented before me. I resisted the urge to squeeze it and focused on the task at hand.

This was the first time in years I had touched another woman's naked skin in this way and I wanted it to be special.

I began again with the head, neck, and shoulders, calming my excitement and reminding myself to go slow. Coconut oil moistened her olive colored skin as I worked her upper body, exploring the contours and responses of a new female form.

I found that the sides of chest next to her breasts were very sensitive as I moved my hands over them.

Quickly sucking in air, she exclaimed, "Mmmmm, that feels so nice."

"Good," I replied. "Try not to talk and just focus on taking deep, regular breaths."

One doesn't need to be into asphyxiation or breath play to know restricting your oxygen at the right moment can intensify an orgasm. But Yoni focused on ensuring a constant flow of air to delay and prolong the eventual climax. It's a little tricky at first, but the payoff is well worth it.

I continued to work my way down her body, enjoying the experience of touching another woman and the intensity of the moment. As I leaned over, my cock came to rest against her side. She moved her arm slightly to capture my rod in the gap between it and her body. I savored the warmth of her skin against my now steel-hard dick.

I looked over to Jill, who had now recovered and was watching us for a reclined position on the bed -- her head a few feet from Anne's. She nodded her approval and smiled as I continued my work.

I reached Anne's butt and hesitated. Up to now, this was like any other massage -- well I guess any other massage conducted naked with your wife looking on. But I plunged on, working the cheeks in a firm manner to find the muscles underneath and remove the tension. Most of us don't realize how much tightness you carry there from sitting all day until someone tries to release it.

My motions continued, working closer until after I applied another helping of coconut oil I began circling the outer rim of her anus with the pads of my fingers.

Anne had a sharp intake of breath -- I wondered if anyone had ever touched her like this before. But as I worked down and into the folds of the inner thigh and up to where they connected to her sex, she relaxed again into deep, full breaths.

I continued down the legs and quietly asked her to roll over.

Lying on her back, her breasts lay down -- though her now quite erect nipples still pointed to the ceiling. Stealing another glance a Jill, I saw she had begun to lazily stroke her own pussy. She was clearly enjoying the show.

I worked Anne's chest and shoulders, and then conducted a full work over of the breasts. I have to admit I may have spent a little longer than needed here, but it was hard not to savor the first new breasts I had handled since Bill Clinton was president.

I was not disappointed. Anne's rack was firm and pliant, and her response when I touched, tugged, and the rolled her nipples in my fingers brought a shudder to my own body.

It was time for the vaginal massage itself. I helped her raise her knees and plant her feet with room for me to work between them.

I started very slow. This can be quite an experience the first time and if you tense up it is impossible to reach the state we were seeking. First, I focused on the nearly bare skin above her pubic bone and then down the very outside folds of her outer labia. Don't rush, I repeated to myself, almost as a mantra to counter the pent up intensity filling the room looking for release.

Slowly her lips became engorged with arousal and her clit swelled like a large pea under my firm fingers. I realized she was close to coming, even before I had began on her vagina.

Shifting my attention, I gradually worked my fingers into her until I found the puffy pad of her clitoris near the front of her vagina. Rhythmically rubbing with two fingers, I used my other hand to resume attention to the labia and the clit -- which now felt like a ball bearing wrapped in folds of silk.

"Oh. My. God." Anne's head shot up, looking me straight in the eye as her orgasm washed over her. It slammed her head back down against the bed as her entire lower body began trembling lightly. I continued the steady pace, extending the orgasm until she let out a small gasp of contentment and her entire body went limp.

Jill, who had raised herself into a cross-legged sitting position with her arms behind her supporting her weight, leaned over and kissed me hard. I returned the kiss, letting our tongues play in the pleasure of the moment and knowing Anne would need a minute to recover.

"That was pretty good for her first time," said my wife. "I think you deserve a little release of your own. "

Breaking our kiss, she moved her mouth down to take my penis into it. Licking gently, I felt her work over the sensitive bits on the bottom and around the head with the tip of her tongue.

"But I don't mind getting a little action myself while you do," she added, releasing my cock and gently pulling me to her. "You've been working so hard, why don't you let me take a turn."

I quickly obliged, lying on my back with Anne's head next to mine as she recovered.

Jill mounted me, guiding her sex down to envelop my cock. I was so hard and she was so wet that it smoothly slid down to the hilt on entry. She leaned forward, hard nipples pushing against my chest as she again kissed me deeply.

She began raising her hips, setting a slow place that I was fine to follow. I relaxed, letting her do the work and enjoying the pleasure of her quim working its way along my organ.

Jill sat back up, accelerating the pace a bit, but in no hurry to reach the end.

I turned my face and found Anne's just a few inches from mine. She slid it over and we began to kiss as my wife continued to work my cock in and out of her pussy, Jill's hands now coming to rest on my chest.

This continued for a minute or two as we all enjoyed the satisfaction of the moment. But soon my wife broke the silence.

"I could think of a better use for his mouth," she said in a tone that was part teasing and part command. "You haven't gotten to experience what he can do with that tongue."

I smiled to myself. I do quite enjoy giving oral sex and I'm particularly turned on by having a woman sit on my face. Unfortunately Jill can't come in that position, so I don't get to indulge that itch much. And here she was looking out for all of us.

Anne seemed a little surprised, but quickly assented -- rising to bring her folded knees down on each side of my head and lowering her pussy down onto my lips.

I was in heaven. My tongue began exploring a new pussy, one I had just had the good fortune to learn intimately over the past few minutes.

My lips were quickly planted on hers as I worked to find the right angle to work my tongue under her clitoral hood. The taste of a new pussy brought me close to coming right there.

I focused on what I needed to do, using my attention to delay my coming climax. Making this position work right took a little doing and I wanted to get her off again before I was done.

Jill was clearly responding to the image before her as she accelerated both the pace of her fucking and the moans emanating from her mouth. I found myself lifting my pelvis off the bed to thrust into her with each stroke.

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