Our Friend Anne

"We are glad you are up because we have something important we need to talk to you about. Both of us don't want Anne to leave tomorrow."

My wife Jill and her best friend Anne caught me off guard as I awoke from napping to recover from an exciting afternoon of playing with the both of them.

"That's fine," I replied, still trying to shake off my slumber and catch up to the conversation. "Plane tickets are easy to change, and sick days are made to be used."

The expressions on their faces told me that I wasn't getting it. Approaching the bed, Anne said in a quiet, but determined voice, "Yeah, but Jill and I are thinking maybe it doesn't make sense for me to leave...ever."

The realization of what they were suggesting hit me. I let my head slide back down to the pillow and brought my hands up to cover my face. How would that work? Did that mean Anne was falling in love with me? With Jill? With the both of us? My mind raced through the possibilities, quickly becoming lost in the endless list of questions. But they all resolved into the clarity that I was now entering a conversation that had already been in progress for hours. The only thing to do was try to catch up.

I felt both of them climb on to the bed, placing hands on my face and head. Taking their hands in mine and bringing them down to my chest, I saw them looking at me with expressions of care, but also nervousness. They seemed genuinely worried at how I would respond. But a calm came over me as I accepted that we were three people with a closeness and connection built by years of friendship. And that no matter where this discussion ended up, none of that would change and none of us would want to hurt each other.

"Let's go downstairs, so you two can get me up to speed," I said. They agreed, and we made our way downstairs.

Now sitting in our living room, we launched into what was to prove a life changing conversation. Jill started.

"After you began your beauty rest, Anne and I went out to the backyard. And as we were talking, what I think surprised us the most was how natural the last 48 hours had felt. I mean Christ, Jack, you and I just had sex with the first new person in twenty years. Anne stuck a strap-on up your ass. I had my first experience with a woman. And all of that was amazing. But what made me most happy was being there with my best friend, and I knew I didn't want to give that up at the end of this weekend."

"I can see that," I said as I sat next to her on the couch. I rubbed her shoulder and she leaned her head over and rested it on me. "I have to say that considering how many things have happened this weekend, this does feel surprisingly normal. What do you think Anne?"

"I don't know what to think," said Anne, sitting across from us in an overstuffed chair. She had her feet wrapped up under her and her knees clasped together, jutting out at an angle. "I mean this is all kind of crazy. I've moved on from here. I have a new life. Maybe it isn't perfect, but I always felt like I was in a rut here. Like it was never going to happen."

"But on the other hand," she continued. "Being here with both of you over the past two days is the happiest I've been since I left. I can't believe I'm admitting that to you. I'm so embarrassed." She covered her eyes, doing a poor attempt to hide she was on the brink of tears.

Jill rose from the couch and crossed over to her. She knelt down, so that she was looking up into Anne's shielded eyes and placed her hands on Jill's knees. She brought one hand and moved Anne's away to look into her face, an expression of kindness beaming through. "You should never be embarrassed about anything with us, honey. You are part of our family."

The term surprised me, but I was glad to see Anne's discomfort pass from her face as Jill grabbed her arm and guided Anne to her feet as they rose together. They embraced in a close hug that lasted several seconds. Jill brought her by the hand over to the couch and seated her next to me, then sitting down so that Anne was between us. Anne gave me a small smile reflecting her fading self-consciousness about tearing up.

"In all the years we've known you, Anne," I added. "You've been an incredible, gracious friend to the both of us. You deserve happiness in your life. Tell us what feels right for you."

"Well," Anne responded pensively. "That is just it. I'm not sure if I've been honest about what I've wanted - even to myself. I get plenty of guys. You both know that. But after a few months I see them for who they really are and I hit the eject button. Or they do some crazy shit and I have to cut them out of my life. And during all that time I was here, you guys were my constant. The people who were always there if a Friday night went to shit or I needed someone to help pick myself up off the floor after I got rid of another jerk."

"And now I wonder," she said, her tone shifting. "If the reason that those guys never worked out was that this is the relationship I really wanted to be a part of. I mean I've always had a bit of a crush on both of you. You know Jill that I've had a few brief flirtations with the fairer sex and Jack, you are the guy I could never have - quite literally because you were with my best friend."

I felt my prick stiffen as I learned that Anne had also harbored dirty thoughts about me all these years. If this bombshell hit Jill as hard as it hit me, she didn't let on. We made eye contact and I searched hers for anger or jealous. I found none and wondered how I could be so lucky to find such an amazing wife. Although some of this seemed to be a new revelation for Anne in the moment, I wondered how much was a rehash of their conversation earlier today. The silence after she finished hung for a second and I jumped in to avoid awkwardness creeping in.

"We understand," I said, grasping for the right words for the moment. "You have been an incredible friend to Jill, to me, and to the girls over the years. You are truly missed and this a place to can always call home."

"Yeah, but what would it even mean to call this home," Anne responded, doubt entering her voice. "I can't quit my job. I can't tell my parents I've moving back across the country because of I am in a relationship with a married couple. Can I?"

Her voice went up high at the end, as if her mind was wrestling with the ramifications of such a decision. I was about to reassure her, when, to my surprise, Jill jumped in.

"Annie, like I said this afternoon, let's take this one step at a time. No one is going to do anything that doesn't feel right in their heart," Jill reassured her. "And right now my heart is telling me I need to roll a joint."

Jill headed over to where we keep our stash secure from our children's explorations and got out the stuff. I rolled adequately, but she was the true master. Soon we were passing a perfect cone, letting the gentle buzz calm us to the enormity of the path we were considering.

As Jill finished a particularly impressive puff and passed it to Anne, she began the discussion where we had left off.

"You should decide what feels right to you," Jill said matter of factly. "Maybe you should go back and spend a month there thinking about it. Maybe you should move back and get your own place. Or maybe you should live here with us. We don't need to rush into anything and everyone is entitled to change their mind."

"The truth is," Jill said, letting the cannabis pull out carefully buried truths. "I think, at some level, this was meant to be. You two - and the kids - are who I always want to be with. And don't think I didn't know about the sparks between you two. It's not like the flirting and hugs went unnoticed. In truth, I kind of liked it - knowing you two wanted each other. But I was also scared that if you got together you would decide you two liked each other more than me and that I'd lose you. And guilty that I trusted you enough to know you'd never do it behind my back, but never enough to let you act out your desires."

Now it was Jill whose eyes misted up. And Anne who returned the favor of earlier by bringing her in for a long hug, arms eventually coming into motion to rub each other's sides and backs. As they broke the embrace, their lips came together for a touching kiss. "Well, I'm glad you came around on that one," Anne said.

"Absolutely," said Jill, as they continued to stay in close contact and I babysat the rapidly shrinking cone. "I think part of it is that I know you both have resisted so long because you love me and would never hurt me. But also part of me is waking up to just how happy it makes me to include my best friend in this part of my life."

Jill and Anne began kissing again, this time more seriously - like they were cataloguing the new range of sensations they could create together. With Anne's hand now down stroking the insides of Jill's thighs and the joint ready to snub out, I tried to bring the conversation back to decisions.

"Not to interrupt a good thing, but -" I started. But Jill was having none of it.

"I think what we can all agree for now that Anne will push back her flight for a day so we can talk this through properly. I'll take the day off work. Jack I assume you think it's worth doing the same," Jill queried. I nodded in agreement. "Good, because it is starting to get late and I'm not quite done enjoying the time we do have. Anne, would you like to sleep in our bed tonight?"

"That sounds fun," Anne replied.

We gathered ourselves, rose, and moved upstairs. We each separated to complete our respective bedtime routines. Jill finished first, heading into the bedroom as I finished brushing my teeth. I soon followed to find her lying on her back, naked, in the middle of the bed. She patted the spot to her right and I hopped in next to her. Anne arrived last, joining us on the bed to Jill's right. I noted that she was as naked as we were and wondered if Jill had previously disclosed our preference against pajamas.

I decided to get things going, rising up to kneeling on my knees and moving to position myself above them. But Jill brought a hand to my chest, and looking me carefully in the eyes said, "Let's take our time." It dawned on me that my nap might have left me with a little more charged than them, and vowed to let them set the pace.

Sliding back down, I again lay next to Jill, who moved her face over to kiss me softly. I kissed her back, closing my eyes and enjoying the touch of her fingers as they delicately scratched my chest.

Jill turned her face away and began kissing Anne. They both kept their eyes open, fixed on each other's gaze. Slowly Anne closed her eyes and Jill did the same as they continued to mingle tongues and conjoin their lips.

In time, Jill turned back to kiss me again and gently grasped my cock with her hand. After a few suctioning smooches and firm tugs, she again shifted her attention to Anne - now turning her body on the side so that they were facing each. They began their kissing again, but with a new enthusiasm fueled by the pleasure being shared between them. They continued for several minutes, each one taking regular pauses to release a gasp or moan of ardor. As I watched, I saw both of their hands begin to play across the other's body - a deliberative exploring necks, breasts, thighs, and snatch. I remained on my side, slowly palming my engorged dick with occasional strokes as I enjoyed the show.

Jill brought back her hand, and establishing a firm handshake with my prick, broke off from her kissing and said, "Please join us." I shifted myself until I was pressed against her, my cock nestled in her butt cheeks. She leaned back her head, offering her neck to me. I planted a row of kisses down it. She shifted her head forward to begin kissing Anne again and I brought my hands around her to begin massaging her breasts. I began softly and avoided the nipples, but soon worked up to strong squeezes. Shifting my grip and attention, I began to capture her nipples between the gaps in my fingers, using the position to rub and tweak them as I continued to work the rest the breast. Jill let out an exclamation of "Mm, yeah, that's nice," and slid her rear back into me more firmly. The motion provided more friction as my dick rubbed against her. Anne brought her hands up to see what had spurred Jill's response and, finding the nubbins of Jill's nipples peeking through my fingers, began to caress them with the pads of her thumbs. Jill's breath caught in her throat and she gave a little tremble as she remained tight against my body.

Anne's hands withdrew, and one went up to Jill's mouth who took in a couple of digits and sucked them hard. Anne's hand went back down between Jill's thighs. I followed suit to find out what was happening, discovering Anne had a firm grasp of my wife's labial lips and clit between two fingers and was stroking the clitoral hood with her thumb - my wife's saliva providing the lubrication. Jill groaned again, and then added "Anne, I think it is time Jack got us ready." In our bedroom code book, that meant eating her out until she creamed herself and was well ready to take all of me. I wondered if Anne knew that, but figured she would work it out pretty quick.

Jill shifted to lie on her back, exposing her already aroused sex. Moving my mouth down on to it, I found Anne had already done much of the work for me. A healthy supply of natural lubrication had already moistened her lips and her clit was pronounced and noticeable even on the first pass. I began using slow, broad strokes to stimulate her lips and tease the entrance to her vagina. Shifting to bring more attention to the skin surrounding the clit, I used small, precise licks and heard a soft moan of approval in response. Checking on Jill's face, I saw it was again engaged with Anne's as Anne also played with one of Jill's breasts. I smiled in approval at the sight and put my head down again.

With the clit sitting up like a dog waiting to be petted and Jill's sex smooth and silky with wetness, I began using my tongue more roughly, adding two fingers to alternate holding down her clit and labia to use my tongue on them or using the digits to rub and stroke her directly. A grunt of response was muted as her and Anne's mouths continued their play. Jill's scent changed as her pussy shared its perfume that let me know her climax was near. Flicking my eyes up, I saw Jill was almost writhing and Anne using her hands on Jill's breasts to restrain her friend.

Pulling her mouth away from Anne's, Jill gasped a lung full of air and unleashed a torrent of gibberish. "Oh, shit. That's - oh yeah, mmAAAAAAA," she exclaimed, transitioning to a high-pitched whine at the end. I could feel the orgasm as her legs locked and her pelvis sought out higher ground to escape my tongue as it continued fiercely stroking her nub. It wasn't as long as last night, but she continued to groan and gasp for several seconds as I let my ministrations gradually subside.

Looking up, I saw her smile and then flop her head back into the pillow. I moved, positioning myself to take the near identical position with Anne. She reached her hand down, giving my hair a tousle, and I dived in. I began by gently applying the tip of my tongue to the root of her hood and began exploring the curvature of her labia majora as my hand gently rubbed her mons. She sighed, relaxing her legs and opening herself to me more. I moved inward, still using small, restrained strokes.

The bed shifted and I felt Jill's hands rubbing my shoulders and back. I savored her touch, enjoying both giving and receiving pleasure simultaneously in a new way. As Jill's focus began moving southward, I shifted my focus to slow, firm licks of Anne's clit and hood. Her legs bucked and jutted forward, suggesting for a second that she had come suddenly.

Instead she smiled to herself, bringing a hand up to her face as she exclaimed, "Oh shit, that's nice." She settled herself again, inviting me to continue. I did, also bringing a couple of fingers in to begin gently fingering around the edges of her pussy. Jill had by now moved her hands down to be gently massaging my butt cheeks. Occasionally she tried to reach the balls and cock that lay trapped under me as I lay prone, but with little success.

As I built my tongue up to a faster, firmer speed, I explored how Anne liked also getting manually played with while receiving oral pleasure. I had known some ladies who really liked it and some for whom a little too much killed the whole experience. Jill was in that later category. Anne was not. Her moans became deeper, unleashing from her throat notes of deep arousal and satisfaction. I soon had two fingers working her from the inside, much as I had during the massage on our first night together. I switched to sucking her deeply inside my mouth and furiously working over her clit with my tongue as I kept her caught between my lips.

Jill's hands encouraged me to spread my thighs and I did enough for her to wrap her fingers around my balls above my testicles and trapping them, stroked them like soft, fragile eggs. I loved it.

Anne began gently rocking her hips and pelvis into me, lengthening the strokes of my fingers and expanding where my lips and tongue continued to touch her as I alternated between drawing her into my mouth and licking her clit at a torrid pace.

"I am going to come so fucking hard," Anne announced to the room and then proceeded to do just that. Her legs again bucked, this time rubbing her snatch on my face in synch with the waves of her orgasm. I struggled to keep steady contact on the clit and giving up, focused on continuing to stroke with my fingers through the crescendo. I felt a slight gush as my hand received significantly more wetness than I would typically expect - even for a sloppy mouth job like I had just delivered.

As Anne's climax subsided, I removed my fingers and shifted up so that I was leaning on my elbows between her legs. Jill shifted one of my legs and began pumping my hard prick in her hand.

"You made me come girl come," said Anne, smiling with a hint of embarrassment.

"That was so fucking hot," I replied, moving up to kiss her softly on the lips. Jill continued using her firm grip to stroke me. But I felt her bring her other hand to guide my hips and roll over so that I was now lying on my back next to Anne.

Moving up on the bed, Jill lined up on the other side of me. She looked across my chest to Anne, and said, "Let's return the favor."

"Sounds fun. We were texting earlier about all the things we could do together when we blew you," she replied, directing last part to me.

They moved their heads down and, leaning mine back, I let my eye line drift to the ceiling. This was the first double blowjob I had ever received and I wanted to savor the feeling. I gasped as I felt a hand close around my cock and guide it back and forth as two sets of lips gently kissed it. Kisses turned into alternating licks, and then two tongues working the head together - occasionally interrupted by a temporarily withdrawal punctuated by the sound of a kiss. They mixed it up, one sliding the head in and out of their mouth, while the other worked the base with a tongue.

My curiosity got the better of me and I couldn't resist taking a peek. They knelt on each side of me, working together as a team. Two beautiful heads of hair, punctuated by regular flashes of two mouths and tongues lathering my penis. Once I had taken in the scene before me, it was impossible to look away.

Even after our activities earlier, I felt a brief stirring that another orgasm was not just possible, but perhaps eminent. Deciding to save the joy of watching them suck down my seed for another time, I used a finger of each hand to touch under their chins and guide them up to begin another group kiss.

Breaking away for a second, Jill asked Anne, "I've been ready for a good pounding for the last twenty minutes. Do you mind if I go?"