My Best Friend's Fiance

My first thought was, "Holy fuck, if I knew I had that kind of power, I would have used it a long time ago," but I knew it was just a coincidence.

Elaine gasped, "Oh my god."

However, she didn't seem in a hurry to pick up her towel. She casually placed her cup down on the countertop as I stared at those soft, creamy tits of hers. My eyes drifted down her naked torso to her pussy with her lips now visible and down her bare legs and back up again. I studied her naked body, taking mental pictures so I would never forget this moment and for safekeeping in my spank bank. Elaine then turned her back to us, bent over at the waist to pick up her towel, giving me a memorable view of her curvy, round ass. Her pussy was now visible from behind. My dick was rock hard by now. Elaine grabbed the towel, trying to cover the front of her body but one tit was still exposed, took her coffee in the other hand, and walked out of the room. My eyes followed her twitching ass until she was out of my sight.

I then looked at Leo and said, "Sorry for staring like that buddy but damn, Elaine has a nice body. You are one lucky guy."

"Shit, I see her naked every day, don't you think I know that. I can't blame you for looking. I know damn well you weren't going to cover your eyes."

I laughed and replied, "Hell no. You know me. If I see a naked woman, I'm going to look."

Leo laughed too, "I know, I know."

After Elaine got dressed she joined us and said to me, "I think I owe you another apology, Evan. I hope I didn't embarrass you too much."

"Oh, you didn't embarrass me, Elaine. As a matter of fact, you never have to wear clothes around me again."

"Oh, you'd like that wouldn't you?"

"Yes, yes I would love it," I replied with a grin and followed with a wink.

By this time, I was almost sure Elaine was baiting me on purpose and she didn't respond to me other than to blush. Throughout all of this Leo never said a word. I think he enjoyed the friendly banter between me and his fiance. He wasn't angered or jealous by the fact that I saw Elaine naked or by my open acknowledgment that I'd like to see her sans clothing again.

The following few times I saw Elaine she was dressed more conservatively in sweatshirts and sweatpants or other loosely fitting clothing. I was both disappointed and relieved. I was tired of going home to jerk off thinking of fucking my best friend's wife-to-be knowing it would never happen. I had been rejected by plenty of women but I've also enjoyed more accepted offers of sex than had been declined. I chose my prospects carefully and I've had numerous offers of sex that were unsolicited on my part. I was never in a situation where a woman was openly flirting with me but I knew sex was off the table. Quite frankly, it was torture.

There were times when Elaine began to flirt with me again but I resisted falling into her trap, or should I say, I faked a lack of interest. While I pretended to ignore her, I always kept a watchful eye on Elaine whenever I had the chance. We were toying with each other like a cat with a mouse.

Things heated up when Leo, Elaine, me, and date were attending a wedding of a mutual friend. It was nice to get dressed up in a suit and have a nice dinner with my best friend and his future mate. We rented rooms at a hotel next door where the bride and groom had reserved rooms for their guests. This way we could drink as much as we liked without having to worry about driving home afterward. My date, Julie and I got ready in our room and went to the wedding reception where we'd share a table with Leo and Elaine.

Julie is a big-breasted blonde of average height with nice legs and a decent butt. We met in a bar, hit it off and we were riding out a series of sexual romps before we would eventually get bored with each other and move on. It was very typical of my social and sexual life. Julie was wearing a short, tight red dress with her tits popping out of the top. She was a very sexy woman which is what attracted me to her. When we got to the reception, heads were turning to look at my date in her skimpy dress. I looked around but Leo and Elaine hadn't arrived yet. Julie and I were having a drink and talking to some old friends near the bar when I looked up and saw my best friend and fiance approaching us.

Elaine was wearing a very short, black slip dress with spaghetti straps and a deep V-neck. She didn't have much cleavage but her small breasts were pressed up against the satiny material and her nipples were poking through the top. A deep bareback made it seem like she was exposing more skin than the dress was covering. Her lean legs were encased in silky black stockings or pantyhose, I couldn't tell which, and 4-inch open-toed heels that gave her a sexy strut with each step she took. Elaine's hair was curled and she was wearing more makeup than she would normally wear. Damn, she looked good.

We greeted each other with kisses on the cheek and I told her how lovely she looked. As we were talking and drinking, I got a glimpse of Elaine from behind, noticing the fabric of her dress laid tightly across her ass. With the help of her high heels, it enhanced her wiggle when she walked. After seeing Elaine in various stages of nakedness, it was easy to imagine her without her dress on.

Nothing much happened at the beginning of the reception. We had our meal and dessert, watched the cake being cut and the traditional first dances. Once they opened the floor to dancing for the guests, Elaine and Julie dragged Leo and me out there. Leo and I aren't great dancers but there is an unwritten rule for couples at a wedding; if the man fast dances, he should get laid. It's no secret that women get turned on when they dance. Slow dancing doesn't count in the getting laid rule because it's too easy.

Leo and I danced with our partners during the fast songs and stayed on the floor when the slow songs came on. It's always nice to hold a woman in your arms, maybe kiss her neck and steal a feel of her ass when no one is watching. Julie is a very sexy woman but I was stealing glances at Elaine over her shoulder. If Elaine noticed me, I would give her a quick wink.

When the DJ played some slow songs in the middle of the reception, Leo and I exchanged partners. I saw my buddy ogling Julie's big tits and thought he might like to feel them pressed up against his chest but my ulterior motive was to get Elaine in my arms. When we danced, there was some separation between us which allowed me to look at her precious face and captivating eyes. I told her how beautiful she looked and how all of the guys were envious of Leo having such a pretty girlfriend.

"Are you one of those envious friends?"

"I think I'm the most envious of all. The others are picturing you naked but I've seen you first hand," I replied with a wink and a smile.

Elaine blushed and replied, "You've got such a dirty mind."

"Tell me something I don't know, Elaine."

I then held her close in my arms as we swayed to the music. I could smell the freshness of her recently shampooed hair and the alluring scent of her perfume. As we moved, I could feel her breasts brushing against my chest. I could feel a stirring in my dick as it rubbed against her thigh. She must have felt it too but she didn't move away from me either.

As the song ended Elaine and I began to part and I could see her nipples were hard as they poked through her dress. The DJ went right into another slow song so Elaine and I stayed together, swaying to the song. I worked our way into the corner of the dance floor where it was difficult to see us. I was more than a little drunk by now and I said something I probably shouldn't have.

"You know Elaine, you look so sexy tonight, I bet not only are other men picturing you naked but they are probably wondering what you're like in bed."

"Stop, Evan. No, they aren't."

"No, seriously, Elaine. You are probably the sexiest woman here tonight."

"Does that mean you are wondering what I'm like in bed, too?"

"I sure am. If you weren't with Leo, I'd try to find out for myself."

My dick was rock hard by then and Elaine didn't respond but I know she could feel my erection on her thigh. She seemed to sway her hips a bit more to rub herself against me. I had my hand on her lower back, touching her bare skin. I made sure no one was watching us and I let my hand slip down to just above the crack of her ass. Sensing no resistance, I let it drift down further with no response from Elaine. My hand drifted down on top of her ass cheek and when she didn't stop me, I fondled her. She let me grasp her ass for a few moments before she pulled it away. I was happy to get that far.

When the song was coming to an end, I whispered in Elaine's ear, "When I fuck Julie tonight, I'll be thinking of you."

We slowly parted. Elaine's face was flush and I walked behind her back to the table we were sitting at watching her twitching ass and lovely legs the entire time. The funny thing was that if Elaine offered to sneak away to a hidden place to fuck me, I would have turned her down. I honestly would not have done that to Leo. Trust me, the devil in my head would have wanted to fuck her brains out but my loyalty to my best friend would have prevented me from acting on my primal desires.

Leo and I went to get drinks for us all while the ladies went back to the dance floor. When we got back to the table with the drinks, Leo told me how sexy Julie was and hoped I'd have a good time with her after the reception was over.

I told Leo, "Yeah Julie is a very sexy woman and she's great in bed but I think you have something special with Elaine that I can only hope to have someday."

"I know that Evan, that's why we're getting married. She's a freak in bed too. Elaine loves sex and we're going to have a good time tonight, especially after drinking and dancing."

Nothing happened between me and Elaine for the rest of the evening. We exchanged some knowing glances but that was all. At the end of the night, I took Julie to our hotel room and we fucked a couple of times before we both fell asleep. We even had sex the next morning before we left and all three times, I closed my eyes thinking of Elaine. When I came, I fantasized about what it would be like to shoot my load deep inside my best friend's wife-to-be.

Several weeks had gone by since the wedding and I hadn't seen Leo or Elaine. We were all too busy with work and they had family obligations and wedding plans of their own to deal with. I kept dating several women and keeping up with my wild ways. That's the way I'm programmed.

Seeing it had been so long since we got together, Leo and I decided to get a couple of beers together at a sports bar. Elaine was going out with her friends so it was an opportune time for best friends to socialize. After we had a few beers, Leo started talking about their sex life. He had told me previously that Elaine was great in bed and wasn't shy about sucking dick, swallowing, doing anal, and role-playing. However, he went a little further this time.

"Elaine never thought she was a sexy woman. I think most women feel if they aren't a supermodel then they aren't attractive to men."

"I agree, most women aren't very confident."

"I'm about to tell you something in confidence and I know I can trust you to keep it between us."

"Of course, Leo."

"When you started flirting with Elaine, it boosted her confidence. I can tell her how beautiful she is but she thinks I'm obligated to say that. When you say it, she believes it."

I wasn't sure where this conversation was going but Leo had my attention. I was hoping he wasn't pissed off at me so I was getting nervous.

"When Elaine flirts back with you, she feels kind of sexy. To be honest, I've been the beneficiary of her feeling sexy, if you know what I mean. That's why I never got angry or jealous. I knew I'd be rewarded later. I am also confident that nothing would ever happen between you two."

I knew exactly what he meant but was still confused, "I get it, Leo but what's your point?"

"I'm getting there, Evan."

"You sure are taking the long way to get there, Leo."

"Alright, here it is. Elaine gets off showing her body and we fuck like rabbits afterward. To be really honest, I get turned on knowing other guys are checking her out. I don't get jealous, I get a hard-on. That morning when her towel dropped and you saw her naked, well, we fucked all afternoon and night."

"Good for you two but why are you telling me all this?"

"I'd like you to come over the house so Elaine could kinda show off in front of you but on purpose this time."

"You mean you want me to see your wife naked?"

"Well, maybe in some lingerie or something. I don't know, we haven't planned it all out. It will depend on her comfort level too. I trust you not to tell anyone either. The only condition is that you can't fuck her."

"Shit, I'd love to see Elaine naked any time you want, buddy. What are friends for?" I said with a slight laugh. "When do you want to do this?"

"How about Saturday night? Come on over at about 6 PM and I'll throw some burgers on the grill and we'll have some drinks and play it by ear."

"That sounds good to me, Leo."

I couldn't believe what Leo was asking me to do but fuck, it sounded like fun to me even if I couldn't screw Elaine. He even showed me a few naked pictures of her on his phone. One was a full frontal of her standing in their bedroom posing for him, another of her sitting with her legs parted and one of her bent over. I took the phone from him to keep scrolling back and forth and zooming in on the good parts. Leo seemed to like my enthusiasm when looking at her pictures. I could hardly wait for the weekend.

I was excited all day on Saturday and showed up promptly at 6 PM with a couple of bottles of Elaine's favorite wine and a twelve-pack of beer. Leo greeted me at the door and guided me out to the back patio where we opened a couple of beers and began to talk like it was a normal day. He said Elaine would join us in a minute or two and that she was naturally a little nervous. I told Leo I wouldn't rush things and would let her control the pace the whole evening. I was still in disbelief that this was actually going to happen.

When Elaine came out to the patio, she already had a glass of wine in her hand. She was wearing a pair of tight white compression running shorts and a yellow tank top with a bra underneath. The shorts showed off her lovely, round ass, heavenly thighs, and long slender legs. I wanted to strip her naked right then and there but knew I had to hold back on my enthusiasm. I told her how lovely she looked and she politely thanked me.

Elaine sat down next to me at the round patio table and I traced the length of her legs from her manicured, red-painted toenails up to her bare thighs. She was wearing a hint of makeup which I prefer as Elaine is naturally beautiful. Damn, she was gorgeous. I could tell she was nervous so I tried not to stare at her or should I say, I tried not to get caught or make it obvious. My dirty mind was anticipating seeing more but I knew I had to bide my time and let things play out. I became a little nervous too. I've never gotten nervous with women other than when I lost my virginity. I think it was because there were some expectations of what was going to happen and I knew I had to be careful not to ruin things with a stupid comment. I knew Leo said I couldn't fuck Elaine but that didn't stop me from hoping that it might happen.

After we had our first drinks, Leo started the grill and when we were into our second drinks, we all started to relax. That didn't stop Elaine and me from stealing glances at each other. There was a certain tension in the air after we finished dinner and moved inside to the family room. Leo put on some soft music as we continued to drink. I think Elaine was feeling some silent pressure from both Leo and me wondering when she was going to begin her little show.

After about half an hour, Leo said, "Elaine bought some new underwear for tonight. Why don't you show Evan what bought, dear? Would you like to see it, Evan?"

"I'd love to see it, buddy."

We both turned towards Elaine with grins on our faces. She was definitely feeling some pressure. We all knew why I was invited and it was time to get things started. I only hoped she hadn't changed her mind. It was obvious Elaine was contemplating what she should do next under the watchful eyes of Leo and me.

As Elaine stood, she mumbled, "I can't believe I'm doing this."

She then stood up in the middle of the room, grasped the bottom of her tank top and pulled it over her head, and tossed it aside revealing a light purple lace half bra. I could faintly make out the brown of her areola through the lace.

Elaine had a sassy look on her face when she asked, "There, are you satisfied now?"

Leo said what I was thinking, "Yeah, that will do...for now," and he smiled at his fiance.

"You're such an asshole," she playfully replied.

Being the gentleman I am, I told her, "It's a very pretty bra, Elaine. You look very nice in it."

"Thank you, Evan."

I tried not to stare at Elaine as she took her seat across from Leo and me but kept stealing glances at her as we tried to carry on a normal conversation. In all honesty, her bra didn't reveal much more than a bikini top but, for some reason, there is a difference between seeing a woman in a bikini top versus her bra. Maybe it was the lace and the fact women try to hide their bras from view but it was sexy to see Elaine sitting there in her bra. She doesn't have big breasts but it was a half bra that revealed some of the globes she did have and was enticing because it was just enough of a tease to make me curious and want to see more. The bigger tease was anticipating more to come. This was only the start.

As we drank and talked, Elaine felt more at ease with the situation assisted by the alcohol. I also believe she liked the attention she was receiving. While Leo and I weren't commenting on her attire, there was no doubt our eyes kept focusing on her chest. After Elaine went and got us another beer, Leo pushed things along once again.

"While you were gone, dear, Ethan and I were wondering if your panties matched your bra."

Elaine modestly replied, "Why, yes they do."

"It's difficult for us to know that unless we see for ourselves."

Without saying anything, Elaine stood up as Leo and I focused on her every move. She took a sip of her drink, then placed her thumbs into the waistband of her shorts, and began to tug at them. As she pulled them down, more of her light purple lace panties came into view. There was a thin string that held the front triangle panel that was all lace except for the part that covered her pussy. It was a perfect way to tease us. Elaine turned around and wiggled her hips pulling her tight shorts down over her hips revealing the back of her panties. It wasn't a thong but had lace that covered about half of her cheeks but it was so sheer there was nothing hidden.

Elaine doesn't have a fat ass but it is nice and round and when you see her from the side you can see how her cheeks protrude from the rest of her body. Her ass is curvy enough to get a good handful of fleshy meat. The lace was so sexy, hiding but not hiding her bare skin at the same time if that makes sense. Lace underwear is designed to be sexy and Elaine's was definitely sexy.

As my eyes scanned Elaine's more than half-naked body all I could say was, "Wow."

Leo told her, "You look sexy, babe, very sexy."

I added to what Leo said by telling her, "You've got to be the sexiest woman I know, Elaine. You're gorgeous."

Elaine was speechless. It was obvious that Leo and I had erections so we weren't exaggerating. I think she was feeling self-conscious and sexy at the same time. She blushed a little as Leo and I continued to scan her body with our eyes from her hair down to her toes and back again. I don't blame her for feeling uncomfortable given the circumstances but I was still enjoying seeing her in her skimpy underwear.