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Night Alone with Holly

"Holly wanted to enjoy some time alone and learned how to share a double and liked it."

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It was the middle of another busy week, a Wednesday afternoon, when Jerry called me at the office to let me know that he and Jennifer had to go to the kid’s school for a parent-teacher’s conference and wouldn’t make it to Happy Hour. I understood and told them that I would see them that night, if they didn’t get back too late. I still had a couple of hours work left to do before leaving and didn’t have to worry about what time I left.

Finally, around six-thirty, I decided I’d had enough and I’d make it to Happy Hour for at least one drink. I was the last one in the office on my floor and had just shut down my computer when my office phone line rang. At first, I contemplated not answering. But, I just couldn’t walk away. When I answered the phone, I was pleasantly greeted with Holly’s bubbly voice.

“I was wondering if you were coming down to Happy Hour? Nick is out of town until Friday and I thought you, Jennifer and Jerry would be here. I’ve been here an hour and nobody’s made it yet.”

I went on to tell Holly about Jennifer and Jerry’s night at the kid’s school and why I worked late but told her I was on my way there if she wanted to wait. She was glad to know I would still show and told me she would order drinks so that I had one ready when I walked in the door.

Lucky for me, the bar isn’t far from the office or home. I was there in fifteen minutes with ten to spare for Happy Hour. When I walked in, the bar was crowded with people waiting to go to the restaurant side of the bar and grill. I saw Holly sitting at the bar speaking to two couples, neither of whom I knew. Again, as always, Holly was dressed to the tens. This night, she was dressed in a black suit with a red blouse and red stiletto heels. The suit accentuated her hourglass figure, awesome legs, and voluptuous thirty-eight double D breasts. She was striking.

Holly saw me as I approached and smiled. She paused in mid discussion with the two couples to reach a hand out and pull me close for a kiss on the cheek, introducing me to them. Keri and Dan were Holly’s clients. Holly explained that she had just showed them a home before heading to the bar. They were discussing the possibility of placing an offer on the home. The other couple happened to be friends of Keri and Dan, Trish and Roger. Both couples were in their early thirties and looked like they had just left their jobs for the day to see the home.

Holly handed me my drink and I took a sip, studying the group and Holly. It didn’t appear that they had more than the one drink at this point. They were deep into the discussion about extending an offer. Holly put her arm around me and pulled me closer to her. Her Obsession perfume was intoxicating and I felt myself stir. She let her arm slide down to my side and gently rub my thigh inching close to my now hardening member. The others were blocked from the view. She knew what she was doing and was quite a tease.

Keri and Dan decided that they wanted to make an offer on the house tonight. Holly was ecstatic. She was ready to take them back to the office to work up the offer and extend it to the sellers that evening. I was glad for Holly but disappointed that I might miss the opportunity to enjoy her that evening. As they got ready to leave, Holly leaned in and whispered in my ear. “Don’t worry baby. This will not take long. I’ll call you when I’m done.”

Holly covered their tab and made her way to the door. I watched her turn and smile just before leaving the bar. Oh well, I thought, might as well leave and head home.

I had just closed the garage door and entered the house when my home phone rang. The caller ID listed the call as Holly’s cell phone. I answered it on the fourth ring.

“I was just about to hang up and call your cell.” She asked, “Are you indecent yet?”

“Not yet,” I responded. “I’m just walking in the door. What do you have in mind?”

“I’ll be there in about thirty minutes. Leave your garage door open for me to pull in. I have the night.”

“Ok,” I replied. “The garage is open. Just pull in and press the button. Inside door is open. I’m not sure if Jerry and Jennifer will drop in or not this evening. See you soon. I’m taking a shower.”

She hung up after saying she would be there soon. I placed the phone back in the cradle and placed the mail in the basket on the counter to go through later. I moved upstairs to the master bedroom and prepared for my shower. I was drying off when I heard the alarm system announce an open door. Just then, the phone rang. It was Jerry letting me know that they would see me Thursday evening. They decided to get a late dinner with the kids and it would be late before getting home. As I hung up, I heard Holly coming up the stairs.

She entered the bedroom and looked around with a smile. I stood there with nothing on having just toweled off. She smiled and said, “I love a freshly showered man. Especially one who’s cock is hardening right before my eyes.”

She stood there, hands on her cocked hips; head tilted looking as luscious as ever. She’s a stunning brunette, hair down past her shoulders. I moved toward her to take her in my arms and kiss her lightly on the lips once before kissing her deeply, tongues dancing and her hands roaming directly to my cock. “You are glad to see me,” she said slyly.

I grabbed her ass with my right hand and let my left wander up her side to gently cup her breast. She moaned softly. “Yes, I am glad to see you. I thought I might not with you having to do work.”

“I had already drawn up the papers for the offer before we went to the bar. They just wanted to make sure they really wanted to go through with it. The papers have been signed and sent to the sellers. We’ll hear something in the morning. Now, let’s get down to business here.” Her look was sensually inviting.

She took off her jacket and let me unbutton her blouse, exposing her breasts encased in a red lace bra, her nipples hard. Holly isn’t slim by any means, but she is enhanced in all of the right places and she is quite lovely. I leaned in and took in her fragrance of Obsession. I have to admit, that perfume does it to me.

She removed her blouse and turned letting me unclasp her bra. I nibbled on her neck as she pushed her ass against my rock hard cock. I slid my hands down her waist and hiked up her skirt, bending her over the bedrail of my four-poster bed. I let my right hand slide up her leg and hooked a finger in the waistband of her red French cut panties and slid them down exposing her pussy. I loved it, shaved with the small tuft of hair neatly trimmed at the top. I slid the panties down to her ankles and she stepped out of them.

Next, she slid her skirt down her hips, standing there in just a red half-slip slit at her thighs, red lace garter belt, hose, and those red stilettos. I slid both hands between her thighs spreading her legs to let me have access to her now soaking wet pussy. I loved the feel of her pussy juices on my fingers. Her lips were open with excitement. She was quite slippery. I used to tease her about how wet and slippery she got and was always rewarded.

She shimmied out of the slip and let it fall to the floor. She leaned over the rail with her ass pushed back toward me, legs spread apart. I let my hands slowly slide up her thighs, feeling the silky touch of her hose to the garter strap clips. I let my fingers slide up the straps to her waist and then back down to her taunt ass cheeks, slowly down, allowing my fingers to find their way to her open lips. I could hear her inhale as I found her clit.

I gently stroked her magic button. She moved her pussy to put added pressure off and on. In a matter of moments, I could feel her juices begin to soak my fingers. I slid one finger in and felt her shudder slightly. When I added the second finger, her pussy began to pulse. She began to move her hips to fuck my fingers. Her juices flowed. I sent her into spasms when I slid my thumb into her ass as I finger-fucked her pussy. I felt her knees sink and shake. She was approaching her first orgasm.

The rush of the feeling her pussy trying to milk my fingers and her loud moans announced her first climax was so erotic. I loved how vocal she was in the bedroom. She always let you know if you were pleasing her or if you were not quite on the mark. When she let loose with, “Oh fuck, I’m cumming!” I knew I was doing something right.

Her knees buckled slightly again and I knew I could keep this up with her for quite some time. The key was not to let up. I kept up the pressure. I could feel my fingers in her pussy rubbing my thumb in her ass as she angled her hips to get maximum pressure on her clit. I was rewarded with a second climax.

“Damn, I love it when you make me cum!”

I slowly pulled my fingers from her pussy but left my thumb in her ass. “I think I need to tap this tonight. Your hot ass is begging for a good fuck,” I noted.

She wiggled her ass on my thumb and sighed, “You need some lube to fuck my ass, baby.”

I moved her around to the right side of the bed with my thumb still buried in her ass all the way and told her to open the nightstand and get the lube.

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When she did, she also pulled out a long double dildo and asked, “So, can we use this together?”

“Well, we just may have to find out after I have some of your ass first,” I replied.

She moved up onto the bed, letting my thumb escape from her ass. She crawled up onto all fours, moving the pillows out of the way and grabbed ahold of the head rail with her left hand and the double dildo with her right hand and offering me her ass. She still had on her garter belt, hose, and heels. He breasts hung down with her nipples hard. I took my cue.

I immediately poured some Astroglide onto my fingers and a dollop onto her asshole. I slowly slipped on finger back in and then added a second before pulling out to add more lube. When I slid my fingers back in, Holly grabbed the double dildo and slid it lengthwise between her pussy lips gliding it against her clit.

I lubed my cock and placed the head against her hot tunnel letting the head press against her rosebud. She was ready for it but I wasn’t expecting her to lean back against me. I watched the head slowly disappear into her hot tight ass. As I filled her, I felt her fingers furiously dive deep into her pussy. That is an awesome feeling. As I slid out to the head, she grabbed the double dildo and placed a head at her pussy. I felt it slide into her as I slid back into her ass.

We slowly began to fuck. I let her control the movements as she slid the dildo in and out of her pussy against my throbbing member in her ass. As she rocked back, I was buried deep in her and could feel the head of the dildo rubbing along the shaft of my cock, the head rubbing against the head of my cock. Again, she became quite vocal, telling me how incredibly full she felt and that it made her feel as if she were being double-teamed. She went on to say how much she enjoyed have a cock in her ass, pussy, and mouth at the group sessions.

As we continued to fuck, she had two more wet orgasms before I felt myself on the edge. Her third orgasm sent me over the edge and I told her I was going to cum. That started her to rapidly slam back against my cock as she impaled herself with the double dildo as deep as it would go. I let loose a huge load in her ass, one I thought would not end.

My cock slowly softened and began to slip out of her ass, followed by some of my cum I had just deposited. The dildo was still buried in her pussy and she wasn’t letting it go. I lay back against some pillows as she turned over on her back, the massive double dildo protruding from her pussy like a cock. She stroked her clit while the other hand massaged the dildo as if she was still jerking off her own cock. She looked exquisitely sexy with her eyes half closed.

“So, who do you use this one with, Jennifer?” she asked.

“Well, I’ve used it on Jerry and Jen here in this bed and we’ve used one at their home. Jerry and I have shared one with Jen’s coaching. I have to admit, I love it when we do it.” I smiled at her.

“How did you have Jerry and Jen do it?”

“Easy. Jen had it buried in her pussy just like you do now. Jerry slid up to her just like this." I moved into position, moving her legs over mine as we faced each other exposing my ass to her and slid in closely.

“Now, add some lube to this end.” I demonstrated by adding lube to the double dildo’s exposed head as if I was applying it to her cock.

“Hmm, I like watching you do that,” she commented with a leering grin.

I then added some lube to my ass, burying two fingers into my own ass to add plenty of lube. “Now, I move a little closer and we slip the head of the dildo in my ass. It is about as large as Tom’s cock.”

Holly smiled with a gleam in her eyes. “I love watching you and Jerry get fucked by Tom. His monster cock fucking your asses.”

As she finished her comment, she tried to place pressure on the dildo to make the monster head penetrate my ass. I inhaled as she pressed and moaned as the head began to get to that point of breaking into my ass and sliding the shaft into me. Holly wanted to fuck me and fuck me right away. I had her interested in a new adventure and she wanted to do it then.

“Oh damn, I love this… watching the head disappear in your ass. Fuck!” She began to fuck me as she furiously rubbed her clit watching the cock slip in and out of my ass. She began to pull out of me completely, leaving my ass open and slipping it in again. Each time, she would grind her hips making the fuck session an intense fucking.

I love being fucked in the ass and having Holly do it that way was incredible. I loved watching her. “You know, I have a harness too, in case you are interested? Just like the ones used at the party.”

She moaned.

“I even have one that has a cunt and ass plug to keep you filled as you fuck.”

She moaned louder. “Oh fuck, this is so fucking hot!” she exclaimed. “I loved watching you fuck. I want to have us in bed together to ourselves, you, me and Nick. I want to fuck every way we can!”

She began to fuck me harder with a pounding rhythm. She was so fucking sensual and she was so into the fucking that she couldn’t take her eyes off her cock fucking my ass. “I’m cumming again!” She began to squirt heavily as her body shook in spasms.

My cock was growing hard again as she shook, convulsing from her climax. As it ebbed, she began to fuck me again, deeply. She was so incredibly sexy as she concentrated on fucking. Her facial expressions gave away her intensity and concentration. She really was enjoying fucking me as much as I was enjoying her having my ass.

“I want to do this with Nick,” she moaned. “You three have opened our eyes to much more than our vanilla sex lives we had before we found you three. The group is amazing. But, we really do enjoy the three of you together. Will I be able to make you cum while I fuck your ass?” she asked.

“Holly, you keep doing what you are doing baby and I won’t disappoint you. Look at my cock throbbing as you slide in and out of me.”

“Fucking incredibly hot! I would never have done this with Nick before, never.”

She began to change up speeds which would have my cock jump each time she would bury all the way in me, and the breathtaking emptiness I would feel, as she pulled all the way out before sliding back into me. I would inhale each time and shudder from the feeling such erotic intensity.

We continued to fuck. My ass took all that she could deliver. It was quite a fuck session. When I announced that I could feel myself getting ready to cum, she began to pound me with greater intensity, her attempt to “pound it home,” so to say. My cock oozed precum and she began to shout out, “Fucking cum!” Over and over again until I felt the wave hit me.

The first spurt flew up to my neck, the second rope landed on my chest and the third landed on my stomach as my cock twitched and the immense orgasmic pleasure I felt took my breath away.

“Oh, baby, that was fucking incredible!”

What was incredible was my cock kept pulsing and twitching from the climax that seemed like it would never end. She kept that cock in my ass buried to the hilt. Her gaze was concentrated on my ass spread wide and her embedded in me. When she finally moved, she let the dildo slowly slide out of my ass with a plop before pulling it out of her swollen pussy. Her cunt was wide open with her pussy lips red and puffy. We were both well fucked.

Holly kicked off her shoes and snuggled up against my chest. She ran her fingers through the cum on my stomach and whispered, “Now, that was some good sex! When Nick gets home Friday, we need another fuck session.”

I looked over at the clock and I couldn’t believe how late in the evening it had become. I ran my fingers through her hair and she snuggled in tighter and let her hand roam to my cock and grabbed hold firmly at first and then lightly, enough to know that she wasn’t intending on letting it go anytime soon. We both dozed off.

I awoke to Holly sucking on my cock. I was rock hard and she was working on my member and looking up at me to watch for my reaction. I ran my fingers through her hair and she let my cock slip from her mouth. She slowly slid up on me and reached between her legs to guide my cock into her waiting pussy. She was already soaked. She moaned as she slid down on me and leaned forward. “I just couldn’t resist, you were already hard.”

“You are quite welcomed to use me as you please,” I responded.

We began a nice slow fuck session with her on top taking control. Having already came twice in the evening, I knew I would last a long time. She fucked my cock slowly and at times with a deliberate purpose. In this position, I had access to her magnificent breasts and took advantage of them. She climaxed several more times before I finally felt myself ready to cum again. When I did, Holly slowly slid off me and back into her position we had originally fallen asleep in.

When the alarm went off, I reached over and turned it off and still had Holly snug up against me. I had two couples as regular fuck buddies now and all I could do was smile. I was looking forward to seeing what I might enjoy when I got home that evening. Jennifer and Jerry would be back and Holly would still be alone for another day and night. I smiled.

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Written by EnjoyBoth
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