I never needed to take Viagra when i was a younger. I got a hard-on and i was good to go. But one night back in the day, i got the old ‘Whiskey dick’ and needed a boost to get through the night.
This story takes place around 2005. [M]I was 41 years old, but i am always mistaken for much younger. i probably looked around 30 years old back then. I moved to Florida from New York in 2002, lived with my parents for a year and then moved to Orlando with a friend. We lived in this fancy high rise building downtown, not far from the nightlife. I soon got a job as a server at one of the local resorts. This resort had an area that had several restaurants and bar inside and i worked at one of the restaurants. This is where i met [F] Jan (not her real name)
Jan was 35 yo, about 5’8″ and maybe 120 lbs and Turkish, tan skin, slim, long dark hair, piercing green eyes and a sexy accent to boot. I was immediately mesmerized by her. My first day at the restaurant I was to follow her and she was to train me. She hardly showed me what to do and barely spoke to me. I took care of getting her tables their drinks and appetizers and ran all of her food to her tables. She kept all of the tips for herself. At the end of the night she approached me and said that some of the servers were going out for a drink at one of the bars in the resort and i should come along. I didn’t hesitate and accepted the invitation.
At the bar, Jan and I sat at a table alone and she told me everything about herself; She was divorced, had two kids, lived in a house with her sister, brother in-law, her mother and her two kids. She told me about her previous relationships (one of which worked at the resort) and all kinds information you wouldn’t tell someone you just met, but i soaked up all of the information.
We quickly became good friends, exchanging numbers and talking outside of work. I couldn’t get a read on if she was interested in me and i didn’t want to make a move and get rejected, so i let everything just play itself out and see where it goes. One day we were in the kitchen and i was bent down getting something and she walked right next to me. She was wearing these Capri-like pants and her ankle and calf were showing and i gave her calf a little squeeze and she turns around and slaps my hand and says ‘hey, no touching!’. I said to myself, ‘Well, that ends that’. I walked back to this area where servers would hang out and she was there. When she sees me, she says ‘hey, i didn’t know that was you, i thought it was someone else’. Back in the game, baby! I was relieved. We would continue to go out after work and occasionally i would go to her house and fix her computer.
As time went by and i was working there for about a year, i would do little things to see what she would do. If she let me squeeze her calf, maybe i can work my way up. We would hang out and i would rub her back or brush her ‘accidentally’ on her ass and she never seemed to mind. I would usually just say goodnight to her when i would leave the bar to go home, but i started giving her hugs and she always hugged me back. Later, i would give her a peck on the cheek and she would peck me back. I knew i was in, but i decided to just take my time. I would go home and jerk off to her every time i would see her. it was driving me crazy.
Every year in October, this resort had an annual Halloween event and the staff would get to preview it before the public. Several of us from the restaurant met at the entrance to the event. Jan was standing over by one of the other servers. I was close by. The other server says out loud to Jan ‘hey, are you and Burt (not my real name) fucking?’ I was in total shock that this bitch said that right in front of her. Jan said, ‘No!!’ I pretended that i didn’t hear what she said. Jan comes over with the girl and says to me, ‘hey, have i fuck you?’ in that sexy Turkish accent and i replied, ‘not yet!’. Jan turns to the girl and says, “See?’. Now, i was relieved and a little surprised at Jan’s reaction. I was relieved that she wasn’t appalled by the question and surprised at her response to my answer. Things changed drastically after this night.
Jan briefly left the restaurant, but came back. She had taken another server job at another outside restaurant. We continued to flirt and i tried to get a read on her. I knew she wasn’t seeing anyone else because we talked and hung out so much. Her ex that worked there was a weasel and would give her a hard time, but he eventually left her alone.
Around March the following year we got word that the restaurant was changing their theme and we would be getting new uniforms and there would be a new menu. After the relaunch, we continued hanging out with the other server’s from work. We all went out one weekday night. I had to be at work around 8 am and didn’t have a car at the time, so i had to take public transportation, which meant getting up two hours before i had to be to work. I just couldn’t bring myself to say no whenever she asked me to hang out. I was late to work a few times because of hanging out during the week, but managed to not get fired.
Around May of that year, things were the same with us. Still hadn’t made a move, but thing were progressing. I wanted to fuck her, but i needed to know if the feeling was mutual. Two months after the relaunch of the new restaurant, we were told the restaurant was going to be closing down for good and we were all going to be moved to different restaurants/bars in the resort. I knew that we were probably not going to be moved to the same restaurant, so i was a little bummed.
A week before the closing, on a Monday, i get a call from Jan asking if i am coming out to the resort to hang out with her after she gets out of work. Now, by this time, i had a ‘no going out during the week’ policy, but i waived it for Jan. We hung out at the resort, had a few drinks, chatted and i left to go home. As usual, i jerked off thinking about sexy Jan. Tuesday and Wednesday i received the same phone call and i again waived my policy and went out and met up with her. I didn’t drink enough to get plastered, but i still felt the effects in the morning.
Thursday i got home at my usual time and was just hanging out. My phone rings and it is Jan asking if i was coming out.’ Of course i am!’ i said. I remember this night distinctly because it was the night of the new Star Wars movie. This resort had a movie theater on the lower level and the bar we hung out at was on the upper level and we could sit outside and look down at all of the people who were dressed up like Dark Vader, Chewbacca and all of the other characters. We sat there for awhile and then headed to one of the nightclubs, had a few drinks and then to another club, more drinks, and then we ended up at another club. It was getting close to last call and we were outside having a smoke.She was a little tipsy as was I. She started asking me about my ex girlfriends, what they looked like and she was started telling me about her past hookups. I was a little jealous and turned on at the same time. When they called last call we decided to start walking out toward the parking area to beat the crowds. We stopped for a second off to the side and she turns to me and says, ‘what do you think of me?’ I was in total shock as she stared at me with those green eyes. I couldn’t muster up anything other than, ‘i am in love with you’. She then wraps her arms around my neck and proceeds to devour my entire mouth. We made out for about a minute and she says let’s go.
Walking to the car, she just said she wanted to keep this quiet and that she didn’t want everyone at work to know her business, but everyone at work already assumed we were banging anyway. She drove us back to my apartment. This was perfect because my roommate was out of town and wouldn’t be returning until the following week.
We get into my apartment and we were on the couch making out and then she says let go to the bedroom. She gets in the room and starts to take her clothes off and i was amazed at what a nice body she had. It was dark in the room except for the moon shining through the window. I mean, i had seen her in sexy clothes, but naked she was flawless. Her tits were not as big as they appeared, courtesy of a padded bra. No worries. She had big nipples and liked them to be bitten hard. Her pussy was shaved with just a little stubble. her labia was a nice size and i enjoyed sucking on them and flicking them with my tongue. She had a flat belly and a tongue ring. She was wild. She immediately went downtown and started blowing me. She brought me close to cumming a few times and i had to slow her down.She flipped over on her back and told me to straddle her chest and fuck her mouth. Just seeing my cock going in and out of her mouth turned me on even more. After that, we changed to 69. I have never licked a pussy as perfect as hers. I tongued her clit for about 20 minutes. She wasn’t really moaning, but i could tell from the way she moved her hips in rhythm with my tongue strokes she was into it. When it came time to fuck, i put on a condom. I had bought a sample pack online and there were like 50 condoms inside, all kinds. i just grabbed anyone and slapped it on. Now, sometimes when i am wearing a condom, i lose my erection. This happened and she tried her best to get me hard and it wouldn’t budge. She sucked me off and jerked me off, but nothing. She rolled over kind of dejected and said its okay. She seemed a bit disappointed. I somehow got myself hard again and we continued. I finished with her in the doggy style position. Looking at her perfect ass while i fucked her from behind and her clinching my cock with her pussy made me explode.
The next day at work, i walked in and she just walks right by me and doesn’t say a word to me. The entire night, she doesn’t engage me in conversation at all. I know how she was at work. She never really fraternizes and was just concentrated on making money, but she didn’t even come by and say hello. I was really bummed. I saw her in the back and said hi and she just managed a ‘hey’. Now, we worked together for 2 years and were really good friends. She never left the restaurant without saying goodbye to me. If she finished her shift before me, she would always find me in the restaurant and tell me she was going home or that she would be at the bar waiting for me, whatever. This night, she finished her shift and just left without saying anything. I slowly transformed into a depressed state. I was mostly depressed because i had blown a once in a lifetime chance with this hottie and because i knew she probably told all of the other servers about my shortcomings. I finished work and made it my business to go to one of the bars at the resort and get hammered. I cashed out, got dressed, walked out of the restaurant and headed through the venue towards one of the bars. They pipe loud music all around the outside, so it is hard to hear anything, but I faintly heard a bunch of people calling my name. I stopped and did a 360 and lo and behold, off in the distance was Jan and a few of the other servers sitting at one of the outdoor cafe tables. I walked over to them and Jan asked me why i just walked by when they were yelling for me. i told her i couldn’t hear anything because of the music. She says they were all going to the club next door. I was confused and told her i thought she had gone home and she said she was waiting for me. I said okay and we headed to the club.
We are all sitting at the bar and the conversation between the two of us was just one-sided. i would ask her something and she would give me a one-word answer. We just sat there. it was really awkward. i sensed that she was just being nice and hanging out one last time before she blows me off.
The club was about to close and she asks if i am ready to leave. She gave me a ride home. Again, a lot of silence in the car. When we pull up to my apartment, i ask her if she is working tomorrow and she replies yes. I was going to ask her to come in, but based on the events the night before, i decide against it. So i said goodnight and she drives away. I was so depressed and mad at the same time. Mad at myself, not her. I got to apartment, cracked open a bottle of Southern Comfort my roommate had and started kicking them back. I had to take a wicked piss, so i tossed my cellphone on my bed and went into the bathroom across the hall. A few seconds later my cell rang. I was still pissing and there was no end in sight. i knew it was Jan calling. At least i hoped it was her. I basically pissed in the hallway running to my bedroom and got to my cell. It was Jan. She proceeds to ask me what my problem was. With piss running down my leg, I asked her what she meant? Her main issue with me was that i didn’t invite her in. I was complete confused at this point. I had fucked up the night before and she wanted to come back in? I told her i thought she was mad about last night. She says, ‘Mad about what?’. I’m like, OK, what’s going on here. So, she isn’t mad that i was Mr Softee last night? I repeated that i thought that she was mad at me and she again says, ‘Mad about what?’. I asked her where she was and she said she was at the 7-11 down the block. I asked if she wanted to come back and she said yes. Now i was in panic mode. i had been drinking at the venue after work and now i had downed about four big shots of SoCo. I could not deliver another performance like last night. She would be at my door in about 5 minutes. I remember my roommate telling me a nurse friend of his gave him some sample Viagra. I had never taken one before, but i was desperate and in a situation. I ran into his bathroom, open the medicine cabinet and there they were. I popped one of those blue pills in my mouth, swallowed it and ran down the hall of my apartment to let Jan in. We walked down the hall back to my apartment, my arm around her waist, kissing her on her neck. We get in the apartment and she smokes cigarette as we chat. I am sitting on the coach off to the side. She come over and sits on the arm of the couch and takes her foot and starts rubbing my leg. I immediately feel this hot flash overcame me. My cock started to grow and it felt like it was going to burst. She was very surprised at my hardness and we started making out right there on the couch. She unzip my pants and released my raging hard-on. She jerked it a few times while tongue kissing me. She removed all of her clothes and i got a better look at that gorgeous body, this time in the light. She was about a b cup, big nipples. I removed my clothes and she gave me an awesome blowjob. Her tongue ring was driving me crazy and i had to make her slow down. She was so turned on that she stood up and sat on my hard Viagra dick bareback. I was super surprised that she did that, but I didn’t care. I knew her long enough to know she wasn’t a whore and she didn’t do drugs, so i wasn’t worried. I wasn’t sleeping around and always used a condom when i did. She rode my cock reverse cowgirl for awhile and then took my hand and lead me to the bedroom. We fucked in every position for about an hour. I was surprised i didn’t blow my load, but for some reason the Viagra desensitized me. I put on a condom and we fucked some more. After awhile, she asked me what position i wanted her in when i was going to cum. This time i wanted to see her pretty face when i came, so i positioned her on her back and i was on her side like spooning her and entered her. I was still hard after an hour and she seemed to be worn out. I think i proved my point after this fuck session and finished inside her hard and deep (well, inside the condom.) We lay there for awhile cuddling and she got up to go home.
The next day, she called me and said she was really sore. I felt bad that she was sore, but was glad i got another shot at fucking her. After that, i never used Viagra with her again and was able to maintain a hard-on the whole time, even wearing a condom.
We continued fucking for about 3 months. She had told me she had issues with dryness down there, not getting wet, so i went to the drugstore and bought some K-Y jelly. This stuff is awesome. It feels just like saliva. You out some of this on your junk and some in her pussy and you are good to go. We used a whole bottle in a few week or so. Never got any Anal from her, but i think she would have been down with the right amount of alcohol.
Things fizzled a few months later and we lost contact until she located me on Facebook. She is married to someone now and we chat from time to time, but i will always remember those few months i got to fuck this gorgeous, sexy woman.
Source: reddit.com/r/gonewildstories/comments/6czq15/the_night_that_viagra_saved_the_daymf