Ever had a girlfriend/wife with that one friend you absolutely can't stand? The one that will forever give you the "you are not good enough for my friend" vibe? Yeh, that was Holly for me. My wife Anna has been friends with Holly since high school and the two even shared a dorm and who knows what else in college. The pair are pretty tight. I love Anna and have begrudgingly tolerated her abrasive friend for the last ten years. Anna is a five foot three, blond with a tight athletic body and medium breasts, while Holly is quite the contrast and towers over Anna at five foot eight, dark chestnut hair and sports a very custom built chest and curvy hips. The two have probably drawn male attention since they hit puberty.
Now in our thirties and well into our careers, Holly was largely out of the picture until that fateful day I came home from work and found the two of them lounging in our living room. I put on as happy a face as I could and she gave me a surprisingly tight hug. We chatted and drank a little before I retired to my office, while the girls stayed up. Anna later explained that Holly needed a place to stay as she had gone through a rough breakup and left her job in the same week. Holly has always been very type A successful, so I found that a bit hard to believe and absolutely did not want this woman in my house and Anna knew it.
"What can she do to convince you it'll be ok?" Anna asked with a bit of a pout.
Without thinking I replied "She'd have to suck my dick and take it in the ass before I'd even consider it!" I immediately regretted the response as Holly is still Anna's best friend and I respected that.
Anna looked at me with a raised eyebrow and replied "How do you know she wouldn't be into that?" I assumed Anna was placating me and was ready for a shower and bed after a long week. Anna went back downstairs to continue her visit with Holly and I passed out.
I woke the next morning to a warm hand on my cock and my lovely wife staring at me "I took care of Holly and I have a fun surprise for you tonight" Anna said in breathy voice before abandoning my hard on and wiggling her ass off to the bathroom. I love that ass and watching her is always a delight, maybe some day she'll even let me fuck it.
It was an uneventful Saturday that wound down with the two of us at a local Italian place, downing more than a few glasses of wine. "Are you ready for your surprise?" Asked Anna with a playful smile.
"I'm ready to finish what we started this morning" I replied, tracing light kisses across her neck as we headed to the car.
Once home, I grabbed a drink and went through the mail as Anna dashed to the bedroom. By the time I made it in, she was dressed in a bustier, thigh highs and stilettos looking absolutely stunning. "I like my surprise" I massaged her firm ass as we kissed. Anna responded by grinding her hips into me and stating "This isn't the surprise at all..." With that bit of implied mystery, she pulled my clothes off and pushed me into a chair. I could only stare at her and ponder how gorgeous she was. The staring ended as a blindfold slid over my eyes and Anna's sexy voice whispered into my ear "Do you want my mouth first?" without waiting for my answer, she slid down my body, pushed my legs apart and had both her hands and mouth on my hard cock. The blindfold made the sensation even more intense and I was in heaven. Anna pulled away making me groan and then went back to using just her mouth. I could now feel my dick bumping the back of her throat, probably the first time she's been that deep. I vowed to buy more of whatever that wine was.
Anna's hot mouth was bobbing up and down on my cock and I could not help but put my hands in her hair and fuck her face. She whispered "that's really hot" in my ear and as my dick was wholeheartedly agreeing, my brain began doing some confusing math. I went to pull off the blindfold, but was stopped by feminine hands. "Let's enjoy the moment before you see who's mouth you're fucking". Hard to argue and whoever's mouth was on my cock was doing a superb job.
"Fuck her face baby, I want to see you push your cock into our little sluts throat" Anna pleaded before her soft lips hit my own. "Do you like having a little slut sucking you while you kiss your wife? Is that as hot to you as it is to me?" Anna didn't let me answer as her lips crashed into mine again. "Is she doing a good job baby?"
I responded, "she's not as good as you (I missed the hand action), but she does seem very motivated."
Anna tweaked my nipple and replied "she is very motivated, I cuffed her hands behind her back and told her she had to make you cum or I'd help you finish in her virgin ass."
I nearly came just hearing her say that, we've dabbled in dirty talk, but this was a whole new level. "In fact, there's a remote control plug in her ass to warm her up" and with that I could hear a subtle buzz and the mouth on my cock moaned powerfully enough to send vibrations through my entire groin. It was at that point things finally added up. The wonderful mouth desperately trying to make me cum had to be my arch rival Holly.
"That's Holly, isn't it?" I asked between gasps. With that Anna pulled the blindfold off and as my eyes adjusted, I was treated to an amazing sight. Holly had her knees on the floor and was prone over the footrest that matched the chair I was sitting in, naked with her hands cuffed behind her back. The image was made even sexier by the mascara running down her cheeks as she focussed 100% of her energy on my hard cock.
"You said she could stay if you could use her mouth and ass, right? Well, I told her that and she jumped at the idea. Turns out the bossy Holly is quite the opposite in bed" and with that Anna once again triggered the plug in Holly's ass and I suspect she came as the moans vibrating through my cock where now combined with a squeal that sent a sensation into my dick I will forever try to recreate.
"Are you enjoying her slutty little mouth or would you rather finish in her ass?" With that said, Holly doubled down and I put my hands back in her hair and pumped my cock down her throat. "That's it baby, fuck her mouth, I want to see you cum down her throat, make her take your cum" Anna's voice trailed off as she moved behind Holly and fingered her pussy "she's so wet baby, I think she really likes being used like this" Anna shared as she looked me dead in the eyes and fingered her own nipple as well.
I couldn't take any more and with two handfuls of brunette hair, pumped my cock into Holly's mouth and blew shot after shot of cum, groaning as she swallowed and all the while Anna pumped her hand on Holly's pussy. As I came back down to earth, Holly was still shaking and had clearly orgasmed again.
I layed back trying to catch my breath just as Anna came back over and sat in my lap facing away, pulling Holly's face into her pussy "I need to cum so badly, I don't care if the tongue is male or female". Moaned Anna as a surprised Holly resigned herself to serving her friend.
Anna's hot little ass wiggled on my cock as Holly did her best to make her cum. "That's it my beautiful slut, a little suction on my clit, be a good girl and make me cum". Uttered Anna as she pressed the anal plug vibe remote to full. Holly wiggled and thrust her face into Anna's very wet pussy as both neared orgasm. I reached around and pinched both of Anna's nipples as her head tossed back and she came on her best friend's face.
Covered in a sheen of sweat and all of us breathing heavy, Anna turned her head back and asked "Do you like your surprise? Think you'll be ok with Holly spending some time here?"
My renewed hard-on now pushing into her ass was probably answer enough, but I still responded with "I like Holly much better when my dick is in her, but are you ok with that?"
"I would probably have said no if you had asked me last week, but after we spent last night drinking and talking, the lovely Holly came clean that she's been attracted to me since high school and a bitch to you because of it. I've always thought she was attractive as well, but had no idea she was submissive in bed until our chat" explained Anna. With that Holly looked up, makeup smeared all over her face, the sheen of our cum surrounding her bright red lips and nodded with a shyness I had never seen from her before. It turned out, under that control freak exterior lurked, an until now dormant submissive with a touch of a humiliation fetish.
We all relaxed and took in what had just happened, while Anna wiggled her ass on my growing hard-on, before rising and pulling me by my hand to follow her. "Little Holly has several more holes you may enjoy" uttered Anna as we both knelt behind the prone Holly. Anna stoked my cock and aimed it at Holly's wet pussy as I grabbed her hips and pushed myself into her friend.
Holly moaned and her head rolled back, while Anna undid her cuffs. "Ok Holly, be a good fuck for my husband" breathed Anna as she sat back down in the chair we had previously occupied. With that, we could make eye contact as I fucked her friend in slow deep strokes, grinding into her and soon bottoming out. Her pussy felt amazing and I knew I'd get to enjoy it for some time as my second orgam would take a while.
Holly moaned "fuck me, please fuck me" in a single syllible utterance. Anna looked at me with pure lust, she was getting off on this nearly as much as I was. "Fuck her harder, make her beg for your cock, she's been such a bitch, this is your chance to make her pay" Anna hit the vibe in her ass again and I could feel it through out my cock. Holy hell, what an incredible sensation. Holly was no longer able to form words and emitting more of a groan as her body twisted and shuddered though another orgasm.