My Best Friend's Fiance

When Elaine decided to join us, she was wearing a simple low-cut pink chemise that was as short as a micro-mini skirt. It showed plenty of her legs that I loved so much and her brown nipples and matching thong could be seen through the satin fabric. She could barely look at me so I tried not to stare. I was a bit nervous myself because of the circumstances and I knew Elaine was a touch uncomfortable too. I didn't want her to have any regrets over what we had planned to happen that night. I was fully prepared for the possibility that she might change her mind about having a threesome. I'd be disappointed but that would be better than any of us having any regrets.

After she was on her second drink, Elaine seemed like she was starting to relax and I felt more comfortable checking out her bare legs and looking directly at her beautiful face. She demurely returned my looks. Leo finally convinced her to walk around so we could get a better look at her in her chemise and I think that helped to relax her also. I'm not a religious man but I was praying that I would get the chance to fuck her that night. She looked heavenly in her lingerie as I was able to see her trim body through the fabric.

After about half an hour, Elaine changed into a long, sheer lace black gown with a matching thong and my desire for her grew even more. She was feeling a bit tipsy by now and more comfortable in her state of undress but still a little nervous. I tested the waters by asking her if I could feel the soft material of her gown and she slowly walked over to me. I ran my hands over her ass, squeezing it for a moment then moved my hands across her breasts. Elaine let me run my hands up her legs to her inner thighs but stopped me when I reached her pussy.

"Not yet," was all she said and I immediately stopped. I had to let her control the pace. I was ready to fuck her as soon as I walked in the door but she was going to have to be the one to give me the green light. Elaine hung out with us for a few more minutes before she went to change again. I think this was her way of gradually working her way up to doing more.

Leo only increased my anticipation when he said, "I think this is the last outfit."

"That's good. I don't think I can hold back any longer. Damn, she's sexy."

"Don't I know it. She's even sexier when she's showing off. I'm horny as hell too."

When Elaine returned, she was wearing a royal blue bra, garter, and thong set with matching sheer stockings and clear high heels. I'm a sucker for long legs and stockings only increase my desires. Her outfit cried, "Fuck me" and I was hoping Elaine wouldn't change her mind about having a threesome.

Elaine paraded around in front of us and all I could say was, "Hot damn" and she looked back at me with a devilish grin.

My eyes widened and my mouth hung open. I was lucky I didn't start drooling. I watched her perfect ass twitching as she strutted in front of us. I reached out to touch her stocking-covered legs and she briefly let me stroke the bare skin of her thighs. Elaine had our undivided attention. My dick was rock hard and waiting to be released from the confines of my pants to sample Elaine's hot pussy. It was getting more difficult by the second to control myself but I knew Elaine would let us know when she was ready to take things to the next level.

Leo helped pick up the pace by saying, "Hey, honey, why don't you lose the bra?"

"I will when I'm ready, dear," she replied, letting both of us know she wasn't going to be rushed into anything.

Elaine sat down across from Leo and me and we watched every move she made, just waiting for a sign, any sign that she wanted things to progress further. She rose from her chair and our eyes followed her over to the bar where she poured herself another glass of wine then walked over to the coffee table and set her drink down. While staring directly at me, Elaine reached behind to unfasten her bra but held it tight against her chest, teasing us further.

Leo started begging his fiance to toss her bra aside and I joined in his pleas. Elaine was relishing her being in charge. After watching us plead and squirm for more, Elaine finally relented and placed her bra on the table. Her nipples were hard and begging for attention. She sashayed around the room proudly displaying her tempting, mostly naked body. Leo asked her to come closer, standing between us in front of the sofa. She bent over to pick up her wine and both Leo and I took that opportunity to begin to fondle her succulent ass. Elaine acted as if nothing was happening and allowed us to enjoy her pillowy cheeks.

Leo and I both moved towards the edge of the sofa and continued to fondle Elaine's alluring butt however, we were now closer to her body. Leo started to fondle her soft, creamy breasts so I followed his lead. I swore I heard Elaine moan softly as our hands roamed over her body. When Leo began to suck on her ripe nipple, I took the other one into my mouth. She was definitely moaning now. We were running our hands up and down her thighs and she didn't object when my fingers touched her hot pussy through her thong so I pressed harder.

My finger was now actively rubbing her damp pussy. Sensing Elaine getting hotter, I began to finger fuck her, pushing the satiny fabric into her. She began to run her fingers through my hair so I pushed her thong aside and inserted my finger into her pussy. Elaine was soaking wet. Her knees buckled when I began to rub my thumb against her clit. I knew I was close to living out my dream of fucking her but I still had to be careful not to push her too fast out of fear of blowing this opportunity after getting so close.

It was Leo who suggested, "Let's take this into the bedroom."

Without saying a word, Elaine picked up her glass of wine as Leo and I watched in awe and said as she was walking away, "Well, aren't you two going to join me or should I start without you?"

I didn't need to hear anything more so I grabbed my beer and almost ran to catch up with Elaine with Leo close behind. When we got into the bedroom, she asked us to remove her garter so we could remove her thong. Leo and I got down on our knees to unfasten the clasps holding her stockings then removed her garter belt. We were so close to her pussy I could smell her sexual excitement from her flowing juices.

Leo then asked me, "Would you like to do the honors?"

"I certainly would, good buddy."

I reached behind Elaine and began to pull the string of her thong from between her butt cheeks, then slowly peeled down the front to expose her bare pussy. I slid her thong down her legs allowing her to step out of them.

Elaine then asked, "Why am I the only one that is naked?"

She didn't have to say that twice. It was almost like Leo and I were racing to see who would be the first one to remove all of our clothes. In less than a minute, we were both naked with our erections bobbing in the air. Leo and I are both about the same size with me being a little longer but he was thicker. Now that we were all naked, Leo and I approached Elaine and we began kissing her, sucking her tits, fingering her, and fondling her ass and thighs while she was stroking us.

I was thinking, "Holy shit, this is really going to happen."

Elaine was the one that turned things up a notch when she got down on her knees and began to alternately blow Leo and me. She started by sucking me and I watched as Elaine swallowed my dick. Her soft, warm, wet lips and tongue felt so good on my dick. I couldn't believe my dream girl's head was bobbing on my cock while her hand was wrapped around her boyfriend's hard meat. When she was sucking Leo, Elaine was stroking me with her tender hands, keeping me hard until her mouth returned to orally pleasure me. I grabbed her head and started throat fucking her which didn't bother her at all, taking it like a champ. If I live to be 100, I swear, I'll never forget the vision of seeing my dick between Elaine's lips.

At one point, Elaine had the head of both of our dicks stuffed in her mouth and Leo called her, "a cocksucking whore," which surprised me but it seemed to make her more driven to please us.

It seemed like we unleashed Elaine's inner slut when she stopped sucking us to rub our slippery cocks all over her face. Leo started tapping his dick against her face so I did the same while Elaine tried to capture them with her open mouth. Leo had always told me she was a great cocksucker but I was now experiencing her skills myself. It was also a turn-on to see her sucking Leo's dick when she wasn't sucking mine. Sex is much better when the woman is just as horny as I am and Elaine was horny. After she blew us for several minutes, Elaine got up and walked over to the bed. I didn't want to be pushy so I deferred to Leo.

Leo must have sensed that I was looking to him for direction and he said, "Go ahead, buddy, be my guest. I know you've been waiting for this moment for a long time so you go first."

I layed down on the bed with Elaine and we began to make out until I started to kiss my way down her sexy body. I kissed and nibbled on the nape of her neck working my way down to her breasts. I played with her tits for a while before kissing my way down her torso. I kissed and nibbled down her luscious thighs and legs and even took time to suck on her toes before working my way back up her other leg. I nuzzled her upper thighs and then spread her legs wider, opening her pussy. As I did, I got a fresh whiff of her hot sex as I started to lick her lips. I stared at her open, hot pussy before I dove in and started to tongue fuck my best friend's fiance with him watching at the side of the bed.

Elaine started to squirm and pulled my head closer. I tongued her for a long time, tasting her sweet nectar before I used the width of my tongue to give her lips and clit long, slow licks. When Elaine began to squirm more, I used the tip of my tongue and flicked it against her clit. Just before she started to cum, I started sucking on her engorged clit while flicking my tongue against it and finger fucking her. Elaine clutched my head, raised her hips, and began to squirt her love juices all over my lips and tongue as she reached her orgasm. I wasn't done just yet. I licked and sucked that pussy to two more climaxes before I raised my head to see a satisfied, lustful look on Elaine's face. I knew she liked my oral skills. I was proud of myself and smiled broadly and licked my cum glazed lips, savoring the taste of her excitement.

Elaine looked down at me and said, "I need you to fuck me, Evan. My pussy is so hot right now."

In no time, I found myself on my knees in front of Elaine's spread legs as she offered me her pussy. I lifted her legs onto my shoulders and ran my dick along her wet lips. When my dick was well lubricated, I placed it against her and paused.

I told Elaine, "I dreamt of being able to fuck you someday. I can't believe my dream is about to come true."

"Well, quit talking and fuck me, Evan."

I smiled and slowly slid my erect cock into Elaine's waiting pussy. I wanted to cherish every second of the feeling of my dick sliding into her. She was warm, wet, and tight just like I dreamed it would be. Elaine was so tight, that it felt like she had a grip on my dick. I saw her eyes roll into the back of her head and her hips raise as I pushed deeper. Once I was balls deep in Elaine, I started to slowly rock back and forth and we both started to moan as her hips bucked to meet my thrusts.

I remember looking over my shoulder at Leo to make sure he was okay with me fucking his fiance. I don't think I could have stopped even if he objected but that wasn't a problem. He was smiling, slowly stroking himself while I fucked Elaine. I was also relieved of any guilt that either one of them would have regrets over what was happening. We were all enjoying our sexcapades that night.

As I was fucking Elaine, I kept looking at her pretty face and the look of ecstasy she was showing. I looked at her naked body and how her tits were moving up and down in pace with my thrusts. I would then look down at my dick appearing and disappearing into her pussy and feeling the corresponding pleasure my dick was feeling by being surrounded by her cunt. I've wanted to fuck her since the first day we met and I could hardly believe it was finally happening with the full knowledge and approval of Leo who was watching it all unfold. The harder I fucked Elaine, the more she moaned and writhed underneath me. I knew I was giving her a fucking she'd never forget. What made it even better was I realized it was probably her fantasy to fuck me too.

I was giving it good to Elaine when she told me, "Fuck me from behind. I love it that way."

Who was I to argue with her so I withdrew from her long enough to flip her over. She stuck her ass up in the air and I got behind her, pausing to enjoy the view, and slid my dick into her again. I was clutching her ass and picked up my pace to fuck her harder. She was begging for me to fuck her harder and faster. I was slapping her ass and tugging on her hair as her tits were flopping around.

As I was fucking her doggie style, Elaine told me, "I know you've wanted my pussy for a long time so give it to me good and hard, Evan."

So I started to fuck her faster, my hips slapping against her ass so hard, that the sound echoed in the bedroom.

Elaine seemed to like being spanked as I was screwing and was screaming, "Fuck me, Evan. Oh, fuck me hard."

"I knew you wanted my cock just as much as I wanted your pussy. You've been cockteasing me for too long; it's about time you let me fuck you."

I began to tire so Elaine got on top of me and started to ride my cock. This gave me a chance to clutch her bouncing tits or fondle her gorgeous ass. I could see the look of pure lust on her face too.

I told Elaine, "That's it baby, ride my cock. Show Leo how much you've wanted to fuck me."

That made her squirm and ride me even faster. When Elaine started to get winded, I flipped her over to take her from behind again. She motioned for Leo to come onto the bed. He quickly fed her his cock as we began to spit roast Elaine. She was one hot bitch that night and couldn't get enough dick. Leo was the first to shoot his load into his fiance's mouth and she gulped it all down and sucked him dry. I soon followed by unloading a huge wad of cum into her pussy. My fantasy fuck was over. I slipped my softening dick out of her and saw some of my cum dripping out of her.

As she was licking and sucking my cock clean, I was thinking, "That was some good pussy."

I think what made it so good was all the teasing that happened over the course of a couple of years. There were times when I was looking to get laid and I could go into a bar and walk out with a woman who I'd fuck and never see again. This was different. Elaine and I had a slow tease going since we met. The modeling and slowly undressing for me drove us both over the edge with pure lust until I was finally able to give her a good fucking that we both desired. It was all made possible because it was one of Leo's fantasies to see Elaine fuck another guy. I will forever be in his debt that they chose me.

After we regained our composure, I was preparing to leave because I thought we were done until Elaine asked, "You aren't leaving are you?"

"Well, I thought that's what you both wanted."

"What's your hurry?"

"I'm in no hurry, Elaine. Shit, I'll stay all night if you want."

Leo went to get refills of our drinks while Elaine went to the bathroom to freshen up. We all met back in the family room still naked. After another drink, we ended up back in the bedroom where Leo and I took turns fucking Elaine while she blew the other. We both lasted longer after cumming earlier and Elaine proved to truly be a freak in bed. I fucked her in several different positions and ended up cumming on her face in her mouth while Leo came in her pussy. It was a lovely sight to see my cum splashed on her face and dripping from her mouth. I was disappointed that the evening was ending. I had fantasized about this night for years but it seemed to go by so quickly and now it was over. It was a memorable night for all of us.

The next morning, Leo contacted me and told me that he and Elaine had a great time with no regrets which gave me some relief. Our friendship remained intact which was the most important thing. I told him I'd be happy to join them in bed any time they wanted. I knew it might be a while seeing things were about to get crazy with the wedding coming up soon. I saw Leo and Elaine several times since that eventful evening and things were fine between us. We were in groups of people but that didn't stop me from reliving some of those moments when I saw Elaine. I wondered if she was thinking the same about me.

On their wedding day, I was standing by Leo's side as Elaine's father walked her down the aisle. She looked absolutely stunning in her white wedding gown. Leo was a very lucky man. I couldn't help but imagine her in her bra and panties and what she looked like naked, lying underneath me, sucking my dick or bending over as I fucked her. I didn't know if I'd ever fuck Elaine again but if not, I would always treasure that night. I could only hope I'd get a chance to have another night of sex with her.