My father works for a large Fortune 500 company, and they hold a week-long convention every year. The entire trip is paid for by the company, so my father enthusiastically attends. Our family tags along, but I can not remember a single time we all attended because of conflicting schedules. This year, I am the only other family member attending.
I always loved coming to these conventions. Every year guaranteed new memorable experiences. The last time I attended was four years ago, right after graduating college and before starting my new job. I arrived at the airport on Wednesday, midway through the convention. My vacation time flexibility and work responsibilities prevented me from taking off the entire week. While waiting in line to pick up my rental car, I formulated a response for when people would ask, “Where have you been these past four years?” I figured I would just respond with something along the lines of “I am a working man now. I have bills to pay now that I am out of my parents basement. I needed to save up money to afford one of these fancy rooms. Vacation time with my company is more flexible now. Etc.”
Ever since committing myself to attend a few months ago, I have been growing more nervous every day. After all the things that have occurred over the years, who would not be was nervous. “Who is attending this year? Will any of my previous flings be there? Does anyone know what happened in the past?” I knew all this uneasiness would peak and then disappear once I met up with everyone tonight at the Mid-Week Mixer.
Before driving over, I decided to check into the hotel and drop off my luggage. The hotel website showed that my room came with a mini-fridge, so while at the airport I stocked up on some snacks, Gatorade to fight hangovers for the next couple days, and some bagels for morning breakfasts. Once situated in the room, I showered, shaved, and dressed in casual business attire. The event was from 4:00 – 9:00, and being held less than a mile away, down on the waterfront. I decided to take my rental car rather than pay more money for a cab. Plus, the rental car gave me a quick out in case things got dull. From experience, I know things can get boring when a bunch of company people interact with various levels of management during business/social functions.
I arrived at the event, and the first hour went incredibly smooth. Indeed, all my nervousness faded. I saw many old faces. None of my previous flings was there, so the coast was clear; I was unsure whether they would show up, and if I would have to face the drama that would ultimately ensue. A few of the friends I made over the years were also in attendance. I did not take long before we were all gathered around like old times. It felt like four years ago was only yesterday. Everyone commented how good I looked. I had gone on a big workout push about a year ago, and have been training for a half marathon for the past 6 months.
Everyone at these events always acted very “proper”, my friends and I included. The adults always considered me the party animal of the bunch. They knew that I lead the pack, and were content with us having fun. Nothing ever got out of control and we never caused any trouble. My point being, these social events definitely needed life to them, and I was happy to oblige. When we were younger, I was always the one that found us alcohol and weed. While the parents would be out drinking, we would all be hanging out partying just the same.
Rachel is one of my friends, several years younger than me, and just finished college. Her family has been coming to these conventions for over 10 years. Her step-father is a big-shot with the company, and friends with my father. I remember when Rachel’s parents stayed at our house one week a long time ago, mainly because I had to give up my bedroom so they could have a place to sleep. I will admit, Rachel is not the most attractive person, taking on most of her biological father’s features. There is no sexual attraction between us. Although, she was curious about giving her first blowjob years ago when we were much younger, but that story is for another time. Believe it or not, we were still able to be friends afterwards.
Back to the mixer. During the course of the evening, Rachel came up to me and asked if I still smoked weed. I knew where this question was headed. She knew me well enough that I probably would still smoke once in a while, and she was right. Rachel’s next question however, took me completely by surprise. She told me that her mother, Janet, wanted her to ask me.
One moment I thought all is well, no drama this convention, and the next moment I get this thrown at me. I looked over Rachel’s shoulder towards her mother, where she was mingling with her husband, my father, and all their friends. Chills ran down my spine as I saw Janet looking at me smiling. I immediately began thinking, “Why in the world would she ask Rachel this sort of question?” The only reason I could think of, was to check and see how much trouble our group of friends would get into this year.
I would be lying to say Rachel and her step-father had a good relationship. I would go as far to say it was because she was only his step-daughter. This is probably the reason Rachel and Janet were so close. They shared the same free-spirited personality. I knew that Rachel would most likely tell her mother I still smoked weed and that Janet would never tell her husband, because he would make a big deal out of a harmless situation. Knowing their mother-daughter relationship, I just smiled back at Janet and she looked away resuming her conversation. I felt my reaction to this surprising situation was satisfactory. Out of curiosity, I asked Rachel, “Why would your mother care if I still smoked?” I smirked, sarcastically adding, “its not like I brought any with me on the plane”. Rachel laughed at me, seeing right through my bullshit. She knew that I would have definitely brought some weed if I still smoked, and she was right, I did bring a few joints along.
Rachel’s next statement was a bombshell I was not prepared for. “My mother just turned 42 and has been doing all sorts of midlife crisis types of things with her friends recently. She even went skydiving, can you believe it? It like she has been trying to get some sort of reaction from my step-father lately. Of course he disapproves, so I make an extra effort to encourage her. You only live once right? Anyways, I am not sure, but I think she was asking because she is curious to smoke again. She probably hasn’t smoked since forever ago.” I just stood there in shock, open mouthed, and speechless. “Did I just hear what I think I heard? Janet wants to smoke weed?” I am an adult now, and the thought of smoking with one of my parents’ friends, yeah why the fuck not!?” I looked back over to see Janet speaking to my father, and thought to myself “I guess her and my mother are not much alike after all.” I laughed with Rachel and said, “Sure, yeah, let her know I still smoke and brought some joints, and if shes interested to let me know”. Rachel nodded and smiled as she walked away. Judging from the tone of Rachel’s previous statement, she made it seem like her step-father kept Janet locked in a cage. If your wife wants to go sky diving, why not? Go do it with her. Nevertheless, this was Rachel’s idea of helping her mother and getting back at her step-father at the same time. I was game.
My impression of Janet over the years was that she was artsy and eccentric compared to her formal and reserved husband; he tucks his t-shirts into his jeans, and I believe has a fanny-pack collection. Rachel and Janet looked nothing alike to the extent that when we were younger I would joke with Rachel by asking if she was adopted. Janet was tall, and with heals comes up to my chin. Her hair was shoulder length, very curly, brown with a lot of blond highlights. Janet always wore unique designer dresses, which earned her praise from other women at the events. I am no fashionista, but to describe the dress she wore that night, it was spaghetti strapped, flowing down over her knees, was blueish green, having an almost jungle-like appearance. With her short curly hair, the back of the dress showed off her long neck, with the opening going down to the middle of her back. She had a great figure for her age; definitely a looker.
About 15 minutes later Janet walked up to me. She greeted me with a hug saying, “Hey there Blue-eyes, long time no see”. Janet always called me by that nickname, and I would always respond, “It’s the Irish in me”. After a few pleasantries, I saved her the trouble by cutting right to the chase, “I talked to Rachel, so did you want to get out of here for a while? The buses won’t be coming to pick everyone up for another few hours, and your husband will stay until the end, guaranteed”. Janet blushed a little at my forwardness, but laughed saying, “Yeah I was thinking about it”. I told her that I was going to take off in a few minutes, but not before I say goodnight to everyone, and if she were interested to let me know.
While heading back to my friends, I reflected on what just transpired and laughed, “Not even one day at the convention and I am already getting myself into trouble. It must be because I stayed away for a few years. Oh well, I need to make up for lost time!”. I ended up telling everyone that I was tired from working this week, the flight, and just wanted to rest up for fun tomorrow. While saying goodbyes, Rachel’s step-father came up to me and asked if I would mind escorting his wife back to the hotel because she was not feeling too well. I replied saying “Of course!”, while at the same time thinking to myself, “I guess it didn’t take her long to make up her mind”. Standing there behind him I see Janet trying to fake a stomach ache, and Rachel with a ridiculous evil grin on her face. What had I gotten myself into?
Just before leaving, Rachel’s step-father came up with the great idea of taking a quick few family photos while everyone was dressed up, to use for the annual Christmas card. Janet tried to delay it for another day, but her husband would not take no for an answer. In order to speed things along I suggested that I use my phone, and could text the pictures to Rachel after. Their family lined up together for the first photo. Then Janet and her husband, posed alone, facing each other, pecking a kiss. It was cute.
As we drove, I turned and reached for my bag behind the passenger seat. Janet commented saying that I smelled nice. My reply got a laugh out of her, “Its this new cologne I am wearing. Apparently, it works as advertised”. While she was laughing, I was presented with the perfect vantage point to admire her cleavage without her noticing. Her breasts are not very large, a B cup at most. Watching her breasts move while laughing indicated they were still firm and supple. From my vantage point, it was evident she was not wearing a bra.
I must have been a little too distracted, because Janet then asked, “Are you having any trouble back there?”. She began to turn around in an effort to help. As she twisted around, she placed her hand half way up my right thigh for support. If she moved her hand any further up my leg, should would have gotten a handful of my cock. I could only respond to her question with a stuttered, “Yeah, everything good, just trying to find the stuff in my bag”. She had to notice the growing bulge in my pants.
I finally found a joint, and handed it to Janet with a lighter, asking her to hold onto it until we got out of the parking lot. It was also a way to test her, just to be sure she was comfortable with it. She replied with, “Its been way too many years since I’ve done this, can you light it to get it started?” I took a few puffs and passed the joint back over to her, and watched her do the same. I found myself thinking, ‘I guess she really was free-spirited back in the day”.
The thing about weed, it seems like the instant you smoke with someone, its like you become good friends. Any tension about the taboo situation disappeared like smoke out the window. I told her to smoke all she wants, and in a macho voice I spoke to an invisible crowd saying, “It is my main mission to properly ensure this fine young woman gets to her destination.” Janet looked at at me, laughed, and smiled saying, “Oh? And how are you going to properly ensure such a thing?” I caught her sexual innuendo, but refrained on responding in-kind, instead joking, “Staying sober enough to remember how to get back to the hotel!”. All she could do was continue to laugh and shake her head.
Janet began telling me all about her recent skydiving trip. “You can not even describe the experience. Standing at the plane’s door, looking down. It is surreal. For the first time the clouds are beneath your feet and the ground far in the distance. As you are falling, you feel the weight on your shoulders, down there on Earth, getting caught by the clouds and both swept away together in the wind.” I remember that description, because it was the one and only statement, made by someone stoned, that I thought was poetically brilliant. Janet went on, “Thank you for letting me smoke with you. You have to let me give you some money to repay you. God this brings back memories of the things I did when I was your age, back in college.”
Be it the weed, alcohol or fate, with an innocent expression on my face, I immediately and without thinking came back with “All you are missing now is the sex.”, The look on Janet’s face was priceless. All the barriers between us, created by social formalities, was now shattered. Janet gasped, and laughed, “Sex? When I was young I was not so easily fucked. I would just mostly give blow jobs.” Now it was my turn to be shocked. Did I just hear what I think I heard. Not letting her casual disclosure go without response, “Hey men of all generations will always accept that which is offered.” Janet then brought the conversation back out of the gutter with a laugh, “Hey now young man, what kind of suggestions are you making to this old woman”.
We got back in the hotel and things felt like they were slowly becoming awkward again. Janet was quiet and I was not sure what she was thinking. The only person we ran into was a young bellhop getting out of the elevator. We looked at each other, and immediately noticed that we were both stoned. He and I both laughed as the elevator closed. He seemed to avoided eye contact with Janet, probably because she is much older, thus probably my mother.
I presumed Janet and I would part ways, and I could go back to my room for a masturbation session while the image of Janet’s cleavage was fresh in my mind. I had been single and sexless for several months prior to the convention. I spent most of my time working and training. It had been a long time since I laid back and blew off some steam. Needless to say I was very horny.
Once on the elevator, Janet pressed the button for her floor. I assumed this was where we parted, so I pressed the button for my floor. She immediately asserted, “Where do you think you’re going? You’re not leaving me stoned in my room all alone.” Taken aback, I quickly reassured, “Never. I just wanted to head to my room to drop off my bag so it doesn’t smell up the room”. Janet replied, “Good idea. Alright then, we will stop at your room first.” I was at a loss of words. I mean, what is going on in this woman’s mind?
As the elevator started it accent her phone started to ring. Janet irritably dug into her purse to see who was calling. It was her husband. She looked at me sternly, and whispered “Shhhhh”. So I stand still, and salute. Both of us were trying our best to stop laughing and regain our composure. Stoned and lying to your husband. Priceless.
I stepped towards Janet to eavesdrop on the conversation. She read my mind, and offered her right arm bringing me against her. She held the phone in her left hand, and brought it across her body to her right ear so I could hear. Being so close to Janet was intoxicating. I could smell the vanilla shampoo in her hair and the slight scent of perfume. The way she held the phone pushed her breasts up and together, giving me a spectacular vantage point of her cleavage again.
The phone call started as expected. He wanted to check up on her, make sure she had got back safely, and to see how she was doing. Janet then took the conversation in a different direction. “I am doing alright… I just got back to the hotel a moment ago… I am just going to take a shower and anti-acid and head to bed… No I don’t mind you hanging out with the boys… I’m not sad, just a little upset… I wore this dress tonight hoping to exite you.. Well, it was not just the dress, but also what is underneath… Oh, you ARE interested huh? Ok I will tell you, I am wearing nothing underneath.”
I stood silently listening to this impromptu phone sex session, too afraid to move. It was not like I could go anywhere, stuck in an elevator with Janet’s arm holding me close. Maybe she does have a deviant side to her that she does not let anyone see? As the conversation escalated, so did my cock. This could be trouble, as when I get hard, my cock is strong enough to use as a coat hanger. Standing up against Janet at this moment was very precarious. I strained to think of anything else. I tried to look away, but in vain. I forgot the elevator walls are covered with mirrors. Last option was just to look straight up, but reflecting back at me was a great view of Janet’s breasts. Fuck my life. I could feel the blood rushing to my cock, and I knew Janet could feel it as well. Just then, the conversation changed, and she stepped away.
“Seriously, we were just starting to have fun and you ruin it… Yes, you did… I just think as your wife, your worrying about such a thing is pointless… No, its ok… I am still just not feeling well and in a cranky mood… Yeah its ok. Love you too”
I knew that I was in the wrong place at the wrong time, and I was not sure what to say, so I said nothing. I will admit, although my earlier masturbation plans were foiled, those minutes up against Janet provided me with sufficient fuel for many future fantasies.
As we walked the hallway to my room, I had a reinvigorating epiphany of greater possibilities. I thought to myself, “when I get back to my room, I will put on more comfortable clothing, and then, I am positive she will want to do the same when we get back to hers. Befriend this woman for the slight possibility of seeing more skin when changing? Consider it done.” I also figure that I might end up hearing another fun phone conversation.
Being a gentleman, I opened my hotel room door for Janet letting her in first. She entered and walked straight towards the window, which went from the floor almost up to the ceiling. She spoke up, “Oh wow. Your room has an amazing view of the city compared to ours. You can even see where we were all down at the waterfront. The city lights are like fireflies. You have to see this.” While Janet was at the window I was putting my bag in the closet and grabbed a change of clothes. Walking into the bathroom I responded, “Hold on a few, I am just going to change out of these clothes quick”. I did not want to make her wait long.
When I was done, I turned off the bathroom light and exited to a dark room. I just now realized that we never turned on the lights when we first came in. Temporarily blinded, I turned facing Janet at the big window. As my eyes readjusted, I stood there awestruck by Janet’s beauty as she stood silently staring into the distance. First, only her silhouette appeared. Then, I started making out features of her dress and the curves of her body. The lights from below contrasted with the darkness of the room, illuminating her dress to near transparency. As she leaned over, my head tilted following suit.
I was in a mesmerized stupor. Janet stayed there, silent, until she called out my name. I immediately came out of the trance, and the gravity of the situation began to hit me. I am alone in this dark room with a woman I fantasize, who is a family friend, and happily married. I have a photo in my phone of Janet and her husband kissing after all. I should not be thinking these things, especially at this time. Again, Janet called out my name, this time turning to face me.
“I had been thinking about what you said in the car, and you are right.” Unsure what she meant, I was confused. Janet took a step towards me, “These trips I go on, trying to relive my youth, you were right.” I stammered, desperately trying to remember the conversation. Then she blurts out, “I need sex.” Janet then reached up, and slid off the spaghetti straps on her dress. It fell down to the ground softly, just like tissue paper. “You have what I need Blue-eyes, and you’re going to love giving it to me.”
Her fully revealed nude body left me jaw-dropped. My eyes drifted from hers, slowly down her body. Her small breasts were full and firm. Her nipples were the width of my thumb, and hard as diamonds. He stomach was flat with a barely visible trail of blond hair running from her naval down between her legs. Her pussy was beautiful. She kept a small tuff of hair above, but shaved everywhere else. As my eyes slowly returned to hers I began to envision all the things I wanted to do with this woman. Having her legs wrapped around my face, and then my body. The sounds of her moaning my name.
I was speechless. Possibly unsure of how I would respond Janet starting saying, “My husband and I have not had sex in a long time. We did not even have sex on our anniversary. You heard our phone call. Maybe I am traveling around the country doing all these things out of frustration? Even Rachel has been upset lately, and I think it is all because I am constantly on the go, and not spending enough time with her. The last thing I want is to be a bad mother. Maybe this is what I need? Maybe it was inevitable? The last thing I want is for my family to fall apart. I know you would never want that to happen. So what do you say?” With a wicked smile and wink she asked, “Are you willing to fuck this old lady?”
Seriously, no joke. What is going on? What did I smoke? Am I dreaming or extremely stoned? True to my nature, I spoke words of brilliance, “You are not old.” Epic response. It did not phase Janet. There was no change in her facial expression as began a deliberately slow walk towards me. Janet knew what she was doing. With each small step she spoke, “You did not fully answer the question?” Step. “You know I could tell you were excited in the car.” Step. “I felt you against me in the elevator, and your saw your face in the mirrors struggling to hide it.” Step. “I could see you in the window just now, undressing me with your eyes.” With one last step she came within a foot of my face. “You invited me into your room as a proper gentleman, and now that we are behind closed doors, I will let you know that you do not necessarily need to act like one with me now.”
There was nothing more I could say. She was absolutely right. Any resemblance of a conscience drifted to the back of my mind. I placed my hands on her side, and slowly caressed my hands upwards. Janet closed her eyes and bit down on her lower lip. I stopped as I reached her breasts. Janet whispered “yes”, encouraging me on. I moved my finger tips over her nipples, just barely brushing them. They were already large and hard. I could hold myself back no longer. I wanted nothing more than to fully satisfy this sexually deprived woman.
I took a step forward to embrace her, only for Janet to stop and take a step back. “Before we start I need something to drink. I have some bad cotton mouth. Do you have anything in your fridge?” At this point I was just dumbstruck by the situation, enjoying this ride to hell on a train named Janet. She went to the fridge and grabbed a Gatorade, and tossed one to me. Then, she spoke with a surprise, “Oooo look what I found”. I was not sure what she was talking about, until she showed me what was in her hand.
Janet showed me the package of honey that came with the bagels I bought at the airport. I knew right then what this woman was thinking. I was indeed right on the money when I assumed Janet’s husband had her “caged”. Janet was ready to break free. Opening that package was like opening her cell door, and my cock was the key. Janet dipped her finger in, smiled, and began to rub the honey on her nipples saying, “I know you have been eyeing to taste these.”
How could I resist? I went over and placed an arm behind her back, picked her up and carried her to the bed saying, “You’re right I have been thinking about you all night”. I laid down aside her and begin to delicately flick her nipples with my tongue teasingly, as she continued to drip on more honey. Her breathing changed, and her skin became flushed. She became more aroused with every passing moment. Eventually, I began to kiss and suck on her nipples, switching from one to the next. She was obviously very sensitive, and loving my attention. Hey body began instinctively offering itself to me, noticeable by her moving hips. She desired more.
Sensing her urgency I grabbed one of her ankles, lowered myself down, then grabbed the other. Janet’s hips kept moving, anticipating what I was going to do next, and it was driving her to the edge. When she grabbed the honey packet, I knew she intended on putting some on her pussy as she lowered her finger. Instead, I grabbed her finger and sucked off the honey saying, “Your pussy is sweet enough as is”. Indeed, her pussy was beautiful, and looked as tight as my 19 year old ex-girlfriend’s. Not in a millions years would I have been able to tell she is a mother. I slowly traced my tongue along her calves, legs, and everywhere other than her pussy. After setting the stage, I slowly blew air, tracing my previous path back around, sending chills down her spine. I said, “That is the feeling you gave me when I came out of the bathroom seeing your at the window. Hearing me brought her close to the brink. Janet then grabbed my hair with both hands, and pulled my face straight down on her pussy, just as she thrust up to meet me. I started caressing her body with my finger tips, and lightly pinching her nipples. Her moans became more frantic, and her pussy was leaking. She was begging for release, and her moment had come.
I traced my tongue around her slit, while slowly working two finger inside her. Janet somehow managed to compose herself enough to make eye contact with me. I smiled up at her, and began my assault. I curled my fingers inside her, making contact with her magic spot. Soon as that happened her eyes opened wide towards the ceiling, moans turned to squeals, breathing become erratic, and her legs stiffened. I took my cue and gently bit down on her clit while thrusting my fingers into her G spot as fast as I could. Janet coarsely moaned, “Fuuuuuck”. Her pussy squeezed my fingers out as she began squirting. I watched her legs convulse, and her head swinging side to side. I even got her to speak incoherently. I believe I had just given this woman the most powerful orgasm of her life! I laid down beside her, gently caressing her skin as she came down from the roller coaster ride.
When she recovered she sat up, grabbed some Gatorade to drink, and looked up at me, only to see me with a grin from ear to ear. Janet gave me an “Oh yeah?” look, and said, “Your balls are mine”. She leaned over and grabbed the packet of honey, pouring the remaining contents on my cock, saying “This is the biggest cock I have had the pleasuring meeting”, as she politely kissed the head. “I never came so hard in my life. Now its your turn” as she winked her eye. Janet was like a mad woman inhaling my cock. She was not kidding about her college days. I began thinking of all the times I saw her kissing Rachel and her husband, and now those lips are locked on my cock. The proper socialite dressed up in high heels, now on her knees with her hair and makeup a mess. I could not imagine a more erotic sight, and it is happening before my eyes.
Janet clenched my balls in her hand, preventing my climax. When I could barely take anymore Janet stopped, and smiled. She wanted to prolong my agony and suspense, much like I did to her. “Enough of the foreplay, I remember asking you for more”. Janet slowly moved up my body, rubbing her nipples on me the entire way. I looked down to see my cock throbbing underneath her. She leaned in for a kiss, and our tongues connected at the same time as I felt her slowly lower down on my cock. Janet was so tight and wet. Her husband was a fool for neglecting this woman for so long. We continued kiss, our tongue exploring each other, as my cock further explored her depth. I knew it was going somewhere no man had gone before when she moaned, “God you are so big. I’ve never felt a cock so deep inside me. Fuck this is amazing.” I bottomed out just as felt her cervix with the tip of my cock.Janet felt the same an inhaled sharply, pulling the air right out of my lungs. We were a perfect fit. Her breathing then became erratic as she started to convulse into another power orgasm, collapsing on top of me.
She came to a minute later saying, “Not enough, I want more.” Janet was transforming before my eyes. The look of lust in her eyes was something I had never seen before. Janet started riding my cock in every way possible, and her breasts moved in sequence. We went at it for what seemed like an eternity, with her moaning “Oh fuck!” the entire time. I tried telling Janet that I was close to coming, but she was non-responsive. Instead it seemed like her pussy clamped down around me harder, as she started grinding our pelvises together. “Oh fuck, yes, I want it baby, give it to me baby, I’m so close to coming”. I could not take anymore, this was it. She could feel my cock stiffen and my balls tighten, which sent her over the edge again. Janet thrust down on me one last time to the hilt as I unloaded weeks worth of pent up frustration. Janet is one of my parents’ oldest friends, is as old as my mother, and I just came deep inside her.
Still euphoric from her orgasms Janet started rubbing her pussy. Giggling she said, “Oh my God this is the best sex of my entire life. Fuck, I feel your hot cum inside me.” I looked down between her legs to her pussy close right back up. Her pussy refused to release my cum, and knowing much I had released, it was a site to see. Only afterwards did I think about protection. Sitting up I laughed, “In hindsight maybe we should have considered using protection.” Janet immediately got concerned saying, “You don’t have any diseases do you?”. That was not the response I expected, “Hell No” I replied. I joked saying, “I was just thinking that it has been a while since I masturbated, so you might want to be careful when you start moving around with that bucket of cum inside you.” Janet giggled her retort, “There is plenty of more room for your honey in this pot of mine. Don’t worry Blue-eyes, there won’t be a mess anytime soon.
Something about hearing her words stopped me from going soft. Janet desired more, and I intended on delivering. Janet beckoned me back with her finger saying, “This old lady hasn’t worn you out yet has she”. Not waiting for a response, Janet crawled over on the floor beneath me, and began to suck my balls. While switching between them she would stop to encourage me, “You love my old body don’t you. All you can think about is my firm hard tits. You want to cum inside my tight pussy again? I think big boy here is about ready for round two? How much more cum do you two babies have for me tonight?
Before long I was fully erect. I pulled Janet up off my cock, and she acted like a baby when their pacifier is taken away. I distracted her by pulling her in for a long sensual kiss. The passion was so intense, it was like she wanted to feel as much of our bodies touching each other as possible. Janet lifted a leg and wrapped it around me, inviting me back inside her. Just as I started entering her, her phone began to ring again. It was her husband.
Janet looked at me with the same expression as in the elevator, “Shhh”. At this point alarm bells are going off in my head as I am thinking, “Shhh my ass. You think I dare say a word. I am barely breathing here. Oh fuck, we are fucked”. Janet walked over to the big window and reached out her arm to pull me in just like last time. Except this time she used her left hand, and instead of my waist her right hand grabbed my cock. She had no intention of letting me get away, or letting me go soft.
So here I am standing in font of this huge window, bare to the world, with a married woman who has my wet hard cock in her hand, my cum leaking from her pussy, while she is talking on the phone with her husband. To top it off, every once in a while she would tease me by poking me with the diamond from her wedding ring. Janet loved the thrill of the situation, and so did I.
“Hey honey hows everything going? Oh, that’s good… Yeah, I heard the hotel phone ring while in the bathroom, but those things don’t have caller ID so I had no clue who it was… Its about 8:30 right now, so the buses should be coming by shortly… You’re going out with some of the boys instead?”
At this point Janet looks at me, then turns her back to me stepping away. I assumed their conversation was about to turn sour like in the elevator. Instead, she lined my cock up to her pussy and slid herself back into place, letting out a moan noticeable to her husband.
“Ohhhh… Yeah honey, I am ok… I still am having stomach cramps, but nothing horrible… No, no, really I am fine, go out with the boys. You know they would end up blaming me if you didn’t go out.”
Slowly, we began to rock in unison. I was too afraid to touch her anywhere else knowing she was so sensitive, and it would probably make her moan aloud again. We maintained eye contact through the window reflection the entire time. Whenever I bottomed out, I could see her mouth the words “Fuck me”. Knowing she was talking to her husband at the same time, and any slip at this point would give us away, I was constantly on edge.
“Well I am not really feeling well enough to think along those lines anymore honey… One of the boys gave you one of his condoms? I wouldn’t let you fuck me with that. It has probably been in his wallet for a decade… Ok honey… Yes honey… Ok… Yeah… I love you too… Night”
Janet ended the call and threw the phone on the floor. She raised her arms putting both her palms on the window and began to yell, “Do you see him? My husband is just right fucking down over there. Fuck me. Oh I love your fucking cock. Fuck me. Give me it. Give me what my husband won’t. This is your pussy now. Oh God you have an amazing cock”.
Janet’s knees began to give way, and I knew she couldn’t keep going in this position any longer. I pinched her nipples bringing her back up to me, sending chills down her spine. While still inside her we share a passionate kiss as I slowly walk her to the bed. She laid down on her back, extending her legs over her head. Grabbing her ankles I mounted her. In this position, we both knew I was going even deeper into her than before. I could not longer hold back my animal instincts. I got up on my feet. Grabbing her shoulders, I pulled her to the edge of the bed and began relentlessly thrusting into her. She started yelling, “Fuck me, oh God fuck me, this is fucking incredible. Fill me with your cum. Give me your babies. Fill my fucking womb with your hot cum! Do it now!!!” Suddenly, I felt my feet slip out from under me. I did not relent as my full weight fell down on her. I continued pulling her shoulders back towards me. My cock buried to the hilt was embedded against her womb. She yelped at the incredible sensation. We both loudly climaxed, not giving a fuck who heard us. The feeling on my cock was not describable as her pussy clamped down and rippled around me. I was so hard that it felt like 10 minutes had passed before I slipped out of her, soon followed by a stream of our cum.
Our bodies were spent. We both laid there covered in sweat, breathing heavily. Janet was curled up, her body appeared to be in a state of shock from the intensity of her orgasms. I didn’t know how to react other than curling up behind her, spooning her close to my body. Janet turned her head to kiss me. We both smiled, and I joked with her saying, “Mission Accomplished”. Janet laughed and said, “More than you’d ever know”. Shortly after she began to get her stuff together.
“I need to get back to the room, shower, and get in bed before my husband gets home. You should give him a call. They are all out going out to a bar or something, but we both know bar means strip club.” I responded by saying, “I am not an idiot like your husband. I know a good thing when I see it”. Janet walked over to me wearing that amazing dress, lent down, and gave me a kiss on the forehead. Then, she walked towards the door and said, “See you tomorrow Blue-eyes”.
I took a shower and went to bed. What an amazing night.
The next morning was definitely interesting. I ran into Rachel and she immediately asked what happened last night? I just said, “Not much, we did the deed, went back to the hotel, and went to bed.” Rachel appeared to accept that statement, which let me know I was still in the clear. However, Rachel questioned, “I wonder why my mother is still in bed not feeling well? When I left she was all curled up. I figured she was faking it last night, but I guess not?” I went along with her train of thought adding, “Yeah, I was not feeling to well this morning either. I did not eat too much while I was there, but it could have been the food. She probably didn’t notice until this morning with the weed side effects and all.” We both started laughing just as Rachel’s step-father walked up. He wanted to thank me for escorting his wife home last night, and said I should come out with them next time. He said the night would be on his dime. I smiled and accepted the invitation. Janet did not show her face until later that evening.
From what Rachel said, I thought to myself, “I must have done a number on that woman. Hopefully she is recovering”. However, when I saw Janet next she was all smiles, acting like nothing was wrong. She walked up to me saying, “Hey there Blue-eyes, get enough sleep last night.” Her friendly tone reassured me that everything was back to normal. The convention went on as usual, and finished with nothing more exciting happen.
Several months go by and my father calls me up to say that Rachel and her family are in town visiting. I should stop by and say hello. I wouldn’t dare miss the opportunity to see Janet again, so I headed over. When I drove up the driveway, I could see the family was all there. Janet and her husband were standing arm in arm talking with my parents. I thought to myself, “The two of them appear happier. I’m glad things have gotten better between them”. Rachel came running out to meet me. She excitedly shared, “You’ll never guess what happened. I am going to be a sister!”
I was shocked. I truly did not know how to react. I looked over Rachel’s shoulder, and felt deja-vu seeing Janet staring right at me, with a big smile on her face, as she gave me a wink. As I walked up the driveway to greet them Janet called out, “Hey there Blue-eyes!”. I responded like always saying, “Its the Irish in me.” Only this time, Janet’s husband chimed in, “It’s genetic you know. Our little baby will have blue eyes just like his parents”. Janet definitely looked embarrassed. I can not believe how I was able to contain my laughter.
The rest of the evening was uneventful. Eventually, I had the chance to talk to Rachel and ask how things at home were doing. She replied, “Since my mother is pregnant she seems more happy. I don’t think she is going to be planning trips anytime soon, but she is still going on a winery tour next weekend just north of here. Having her around more and being in a better mood is definitely making things easier at home dealing with my step-father”.
After the evening, I had time to sit back and relax. I checked my email, and saw a message from an unfamiliar email address. It was from Janet! “Hey there Blue-eyes. I am supposed to be going on a winery tour next weekend, but my friend bailed on me at the last minute. Don’t supposed you know anyone that would like to join an old pregnant woman?” I replied, “I’m no wine expert quite yet, but I hear that just like women, wine becomes finer with age.”
As I lay in bed staring at the ceiling, I contemplated all the events that took place until now. I wrote this story so you could go back, reread it, and relive it just as I did. Recalling the minute details from all my interactions with Janet that night, everything began to make sense. Janet’s husband did not want to get pregnant, but she did, and I was the perfect man for the job.