Let me start by indicating that Megan and I have a great life. We love each other deeply, consider each other best friends and have a wonderful sex life. Megan is much more sexually reserved though, and it has taken me nearly fifteen years of marriage to even begin to lure any sexual fantasies out of her. I know she has them, as she is a very creative person, but she is reluctant to share them out of, I believe, embarrassment. I, on the other hand, tend to be a bit more open and comfortable with sharing, sometimes to the point that I fear it freaks her out. To that end, it was on a recent trip when one of her fantasies emerged and we discovered that it was mutual.
I had been planning a business trip to southern California to attend a conference. Now that the kids were all in school, it was much easier for Megan to pull away and join me. I would be busy from early morning until late afternoon most days. We decided that she could spend some time exploring the city, lounging by the pool and possibly getting together with a sorority sister that lived in the area. We would have time to go out for some great dinners and evenings in the city, though.
We arrived late on Sunday evening, having made time on our flight from the east coast. Meg was tired, but I convinced her to join me for a drink in the hotel bar. We jumped on the elevator and headed down. Meg headed a table near a window, overlooking the bay and away from the din of the lounge. I walked to the bar to order our drinks and, as I stood waiting, noticed a guy at the bar staring at Megan. It would have been easy to mistake her for being alone since I had come straight to the bar. I could see that he was definitely checking her out, his eyes going over her repeatedly. She had her chestnut hair pulled back in a short ponytail and was dressed pretty casually, sporting a sheer white blouse with a black tank-top under. The blouse was unbuttoned far enough down to show her cleavage and the roundness of her breasts. She had perfectly sized tits to suit her petite and athletic frame. Her tanned and muscular legs were crossed and extended from under the table, topped by a short pair of khaki shorts. The bartender handed me our drinks, but I hesitated for a moment to watch this stranger admire my wife. She was checking messages on her phone and oblivious to him. He finally broke his gaze as his buddies pulled him back into their conversation, and I made my way over to the table with our drinks.
I made a toast to being on vacation, hoping that she had a chance to relax and enjoy her time. After some small talk about the kids, my thoughts returned to the guy that had been watching her. "You know, there was a guy over there checking you out while I was at the bar," I said.
"Oh, no there wasn't," she responded slightly embarrassed, "No one would be checking me out."
"Yes, yes there was. That young guy over there in the blue button down, he was most certainly checking you out. I watched him the entire time I was getting our drinks and he really seemed to like what he saw." A slight blush rose to her cheeks as I continued to speak. "What wouldn't he like? You're extremely sexy, and those tanned legs are absolute eye catchers."
"You are so full of it," she said, even more embarrassed but loving my compliments. "I'm just another almost forty mom and I'm not even dressed to impress."
"That's what makes you so sexy, though. That's what attracted me to you in the first place. You were casual and laid back, not even trying to be cool or sexy. You've always rocked that natural look." I took a swig of my drink and made an animated glance under the table at her legs, raising an eyebrow and smiling. This drew an instant smirk from her as she sipped her wine.
"You know, I would love to sit in a bar and watch guys hit on you. Just sit away from you and watch them scope you out, come over and hit on you and have you flirt back." She stared at me with her mouth slightly agape over her raised wine glass. "A lot of the girls I dated in college I knew as friends long before we went out, and I had seen them get picked up in bars many times. When we dated, and eventually hooked-up, it always turned me on to think about the other guys they had been with. You've always been hesitant to tell me about any of your past hook-ups so it would be my chance to see you in action."
"My past is really not that exciting. I've told you that. Besides, I bet I could sit at that bar all not and not a single guy would come up and talk to some frumpy mom sitting alone."
"You're not a frumpy mom and, besides, you would be surprised. Single women to men are like blood in the water to sharks, we can smell you a mile away." I pulled my chair closer to her around the table and spoke softly, "I bet you would have a guy on you in a matter of minutes, definitely before the end of your first drink. I would just sit over here and watch him undress you with his eyes from afar, because he would, and then he would come over and try to start a conversation. I'm guessing you would act uninterested at first, not making eye contact and forcing him to put forth a bit more effort. He would offer to buy you a drink and then, as it was delivered, you would finally make eye contact and engage in the conversation. After a while he would casually put his hand on your knee and you might shift your weight towards him a bit, hinting at some level of physical attraction. As his confidence grew, and hormones starting flowing, he might infuse some sexual innuendo into the conversation. Taking cues from your responses, he would try to get closer to you, leaning into you and putting his arm around the back of your chair. I could imagine you turning your seat towards him and opening your legs slightly so that the hand on your knee could move to the inside of your thigh. At that point, depending on how crowded the bar was, he might either try to move his hand up your thigh, or just proposition you to return to his room for a drink."
The waitress interrupted my train of thought and I ordered us another round of drinks. I could see that she was aroused, as the blood had rushed to her neck and face. She stared at me with semi-distant eyes, as if she were still deep in my thoughts.
"Well, am I that far off?"
"I would be so embarrassed if another guy hit on me and, besides, I'm not interested in anyone but you. I wouldn't even know how to act."
"I know you're not interested in anyone else, that's why I'm sharing this with you. I'm totally comfortable in that fact." I let my words sink in for a moment as the waitress returned with our drinks. "So, what would you do?"
"What do you mean?"
"Would you let him caress your thigh, maybe even touch your panties? I mean, let's imagine you're wearing a skirt. Would you let his hand go under it?"
"I don't know. I don't want to think about it."
"Come on, close your eyes and think about it. It's just you and I talking. Would you let his hand go up under your skirt?"
She took a huge gulp of her wine and closed her eyes. "I don't know, I might. Depending on how he looked." I could see her breath deepen and the blush in her cheeks and throat increase.
"Think about his hand sliding up your thigh," I said, watching her as she fell into the image in her mind. Her legs shifted apart ever so slightly. "Think about his hand slowly rubbing up and down your thigh, moving higher under your skirt with each pass until his fingers brush up against your panties. Would you like that?"
Her eyes opened softly and she took another drink of wine. "Yes," she said in a breath.
My heart was pounding and my cock had grown stiff while I talked. "I want to take you upstairs and fuck you right now." I threw some cash on the table and offered her my hand as I stood. She made a devilish grin and nodded. We walked to the elevators and entered the open doors. I punched the button for our floor and walked behind her. As the doors slid shut, I started kissing the nape of her neck and pulled her hips back into my bulging pants.
"Oh my," she stammered, "you seem to be all worked up."
"More than you can imagine," I said, letting my hand course across her belt and down to her crotch. I could feel the heat through her shorts. "Seems I'm not the only one that's worked up."
The elevator doors slid open and we walked quickly down the hall to our room. I opened the door and she took two steps inside, spinning towards me as the door clicked shut. Her mouth was open wide as she pulled my face towards her with both hands. Her tongue was in my mouth desperately seeking mine and she let out a soft moan when they met. I quickly unbuttoned her blouse and slipped it off her arms as I forced her backwards into the room. I pulled her tank top over her head and reached behind her to unclasp the black lace bra she was wearing. We made it to the side of the bed and I threw her down on it, dropping down and kissing her stomach. I moved to her erect nipples, taking each of them into my mouth and sucking hard on them. Nibbling lightly to make them even harder. My tongue coursed around each nipple and glided to her belly button, where it dug in deeply. My hands unbuckled her belt and released the button of her shorts. I pulled the shorts down slowly, letting my tongue follow them down. She lifted her hips off the bed to let the shorts pass easily. My fingers grasped the top of her black lace undies and they slid down with the shorts, revealing her freshly shaved pubic mound. When the shorts passed her knees they fell to the floor and she kicked them off with her sandals in one motion. I pulled my head back slightly to admire her beautiful mound. I could see her slit glimmer with wetness and knew that she had been more turned on by our earlier conversation than I would have imagined. As my tongue traced the outline of her lips, I could taste her juices and smell the heat from within. I ran my tongue back along the inside of her left thigh and back up its length, pausing faintly above her lips before I made a similar track along her right thigh and back. I let my tongue brush the outside of her lips and I could hear her catch her breath in anticipation.
Instead of giving her the immediate pleasure of my mouth, I stood and pulled my shirt and shorts off. She remained laid back on the bed with her eyes closed, never glancing at me. I laid down next to her, letting my hand glide from her knee, up her thigh to her hips and belly, and finally to her left breast. I leaned over and kissed her deeply on the mouth. "Would you have let the guy from the bar do this?"
"Yes," she whispered.
"I want you to think about being in his room. His hands all over your body. His face buried in your pussy and his cock pounding you."
"Ok," she said breathlessly.
My hand crossed across her stomach and between her legs. My fingers touched her outer lips and I could not believe the amount wetness I found there. I slowly let a finger part her lips and slide between. She was hotter and wetter than I could remember since our younger days of dating. Her juices ran down my fingers and the insides of her thighs. Her back arched at my touch and her legs spread open invitingly. I pulled my fingers to my lips and tasted her for the first time that evening. I traced her juices across her own lips and kissed her deeply so we could both taste. I lowered myself down the bed until my knees were on the floor. I spread her legs with my hands and could see the juices flowing from her pussy. I buried my face in her, licking up her juices like a man who hasn't had water in days, sucking them from her every inner fold. I pushed my tongue deep inside her and she let out a deep moan. Her clit was completely swollen and sticking out from beneath its hood. I took it between my lips and sucked on it lightly, pulling gently. She gasped and her hips bucked forward, driving my face into her pussy.
"Make me cum, now, make me come," she gasped.
My tongue immediately went to work, coursing rings and figure eights around her clit. Her hips move methodically with my tongue as she fucked my face. Each push of her hips brought a fresh gush of juices forth from her vagina. She began to whimper and moan with each motion and soon my face was covered with her orgasm.
"Fuck me now. Oh god, fuck me."
I stood and spread her legs further apart, placing the head of my cock at her wet hole. "Are you sure you want this guy to fuck you?" I asked.
"Yes, yes I want him inside me now"
I slowly pushed the head of my cock inside her and found her even hotter and wetter than before. She hungrily pushed her cunt against me to get more cock inside. With one swift motion, I rammed the entire length of my dick inside her. She let out a scream and immediately began quivering with another orgasm. I pushed her knees back to her shoulders and began fucking her hard. Each thrust sent her juices splashing across our stomachs and down my legs. We were soon in a huge wet spot on the comforter. She was moaning with each thrust of my cock and I couldn't tell if she had stopped cumming, or was still in a prolonged orgasm. Her face was completely red with passion and her mouth open gasping for air as she moaned.
"I'm going to cum inside you," I moaned as I rammed into her, my orgasm overtaking me suddenly. The head of my cock was pressing against her cervix and I could feel my hot load filling her. My shoulders shivered while I continued to pound into her, feeling my hot cum mixed with hers. I pulled out of her and watched my cum drip from her pussy and run down her ass crack to the bed. I fell beside her and pulled her face to mine for a deep kiss. "That was amazing," I gasped as I breathed heavily.
"You haven't made me cum like that in a long time," she replied with a dreamy grin. "That was awesome."
We fell into a deep sleep entwined in the bed that night, both of us exhausted from the unbelievable sex. I awoke early the next morning for meetings and, unfortunately, stayed tied up with business for most of the next two days. I managed to say hi to Meg as she lounged next to the pool in-between meetings, but that was the extent of our time together with the exception of some conversation before bed and texting back and forth throughout the day. Finally, I had a break on Tuesday and had a chance to take Megan out for a nice dinner.
I told her that I would meet her at the room and change out of my suit into something a bit more casual. When I opened the door, I found her standing in the room wearing a simple, but sexy, black dress with a fairly low cut front that showed off her great breasts. The hem was high enough to exhibit her beautifully athletic and tanned legs. She had on nice open-toed black heels that flexed her calves and definitely showed off her ass.
"Wow," I said, not taking my eyes off of her. "I'm going to have a hard time competing with that tonight. You look fabulous"
She blushed and demurely replied, "That was what I was going for. I don't get to do this often."
I changed quickly and we headed downstairs to grab a cab. She told me about her day by the pool and shopping in some of the boutiques along the waterfront. We got to the restaurant and hopped out. The place was packed, so we checked in with the hostess and headed to the bar to await a table."
After a couple of drinks and some small talk, she looked me in the eye. "The other night was amazing and I haven't been able to stop thinking about it. I had to go back to the room yesterday to masturbate because I kept thinking how great it had been."
My cock stirred to life in my pants as my mind flashed back to Sunday night and the scenario we had talked about, and the great sex that had followed. "Yes, it's been a rough couple of days in meetings with that on my mind. I found myself spacing out in daydreams a couple of times." I took a big swig of my drink to build the courage for what I was about to say. "What would you think about doing it tonight?" I asked.
"Yes," she whispered, "I definitely want to be with you tonight."
"No, I mean yes, but no," I stammered. "What if we followed through on part of that fantasy tonight?"
Fear immediately washed across her face and she almost dropped her glass of wine. "Oh my god, are you serious? There's no way. I don't want to be with anyone else, I love you."
"Just calm down. I'm not talking about you picking up some biker in a seedy bar. I'm not even talking about you having to go through with anything. I think it would be fun just to try the flirting part we discussed." The horror in her eyes slowly eased away and her jaw unclenched.
"I never thought you were serious about that. I thought you were just talking. I can't imagine actually sitting at a bar and trying to pick up guys."
"Honey," I said in my calmest voice, looking deeply into her eyes, "I've always had a fantasy of watching you with some other guy. I don't even know if I would even e comfortable with that, but I have often thought about watching you ride some other guy. If for nothing else, just to see you from another perspective. You sitting at a bar flirting with some guy would be kind of a fun happy medium. You would be in complete control and it would only go as far as you wanted it. As far as you picking up guys, the way you look tonight would draw them to you like flies to a picnic."
Her eyes dropped to her glass of wine in deep thought. I could tell she was thinking about it, but not sure if it was still in panic or in earnest. When she looked back up at me, I could see a twinkle in her eyes.
"I wouldn't even know what to do. Do you know how long it has been since I've flirted with anyone but you? I would just be dopey and nervous and probably come off like some dork."
Just then, the hostess came to our table to seat us. She led us to a secluded booth for two near the windows in the back of the dining room. A small candle burned low in the center of the table offering a nice ambiance for our conversation.
The waiter visited almost immediately as we sat down. I quickly scanned the wine list and found us a nice bottle to enjoy with our meal. After he left, I leaned closer across the table and talked just above a whisper. "This would be fun. I will be sitting as close as I can without being too conspicuous. You just need to sit at the bar, enjoy a drink or two and look bored. We're in a town with hundreds of military men on station and on leave. They will find you. You just need to carry on a conversation, flirt if you want an see what happens."
"I don't know. I'm already nervous just thinking about it. Look, I'm shaking." She held up her glass of wine and there were noticeable ripples across the top.
We continued our discussion over wine and dinner. She didn't seem to notice that I wasn't allowing her glass to go below half-full. We agreed, her half-heartedly, that we would return to the sports bar in our hotel. I would first find a table near enough to the bar to be in constant and complete eyesight of her, but far enough away that no one would notice me observing. She would then find a seat at the bar, order a drink and see what happens.
After the first bottle of wine was emptied, I could see her becoming somewhat more enthusiastic and involved in the planning. As we ate our meals, we laughed and talked about picking up the opposite sex in college. We both recalled how fun it had been to be single and free, not knowing who or if you might end up with at the end of the night. We recounted uber-drunk encounters that ended horribly laughable situations. I could tell that she was getting into it.
"I'm still nervous," she said as we waited on the bill, "but kind of excited. You promise nothing will happen?"
"I promise. I'm going to be less than twenty yards away from you. If some guy ends up being an ass, you just need to excuse yourself to the restroom and give me the sign." We had agreed that if she twisted her watch as she walked away from the bar, it meant I was supposed to meet her near the restrooms.