I was driving home. What had I done? I just had sex with the big boss. He was married and older. I didn’t intend for this to happen. How did it get that far? I wasn’t going to do anything with him. I had conflicting thoughts. I did have a good time. It was exciting my heart was racing. I had guilt yet it was so exciting. It was the best sex I ever had. Is that so bad? My mind was bouncing all over the place. What does he think of me? At least I am on the pill so I wasn’t worried about that.
Two weeks later we had another department Happy hour. I asked my friend Karen if she wanted to come with me. I would come by and pick her up after work and she would tell her parents she was sleeping over my house. Her parents liked me and trusted me. I told her they don’t proof and as long as you stay away from the bar you can drink. I said the guys at work buy me drinks the whole time. She was into it, besides she always wanted to go to a bar.
She was a friend that I made from working at the convenience store I last worked at. Karen was 17 and very pretty with a great figure. She was half Italian and half Dutch. She was the type of girl I wished I could be. She was outgoing and openly friendly. Where I was very shy and reserved, she wasn’t. She dressed provocatively. She often wore spandex, it was the 80’s and she had that “Bananarama” look. Her hair was long and she wore it high, it was the style after all. She wore lots of make-up and her clothes were tight. Basically she looked like a girl you may find working the streets of New York or one that was in an 80’s rock video. It was the style and she wore it well. I think that is why I became friends with her. I wanted to be more like her. She was so confident plus she was a wild. She had told me about some of her adventures. She had some good ones. She had lost her virginity to a college guys when she was 16. At a school dance she gave the DJ a blowjob in his car. She had sex with a guy she met at a concert in his van. She was exciting.
While driving over to Happy Hour, Karen lit up a joint. I only had a few hits as I was driving. Karen liked to party. Once inside the bar, we were having “free” drinks and talking to a lot of the guys at work. Everyone wanted to know who my friend was. The common comment among the guys to me was, your friend is hot. She wore white spandex pants with a red sweater and red pumps. She had a big hair, blue eye make-up with bright red lipstick. I could never be that bold. After a couple drinks, the bartender also noticed her and asked her for her ID. She said she left it at home and he said sorry but you have to leave. We had parked in the back parking lot and had to walk past Mr. D’ Angelo to get out. I smiled at him as we walked by and he smiled back and nodded his head acknowledging me. We were backing out of the parking space when Mr. D walked over to my car. I rolled down the window.
“Hey Katherine leaving so early?” he inquired.
“Yeah well Karen doesn’t have her ID so they won’t serve her”.
“Oh that’s too bad, so where are you pretty ladies headed?”
“No where really”.
“Well I have the whole house to myself and I have a full bar plus I could use some company. Would you girls like to play some pool?”
I was about to say no when Karen blurted out “yeah sure, I love playing pool”. He said great follow me. I live about 20 minutes from here. When I rolled up the window, I asked her, why did you say yes? She said what else are we going to do besides we can drink and play pool. As we were following him, Karen lit up another joint and we each had a few drags as we were following him. When we got to his house we immediately went down to his basement where the bar and pool table was. First he put on MTV then he made us both a vodka and orange juice. He asked who wanted to play pool. I didn’t, I had never played before and I wasn’t the type to play something I would be bad at. So Karen ended up playing him alone. I was ½ watching them and ½ watching MTV. He was helping Karen and giving her tips as they played. I caught him checking her out a few times as she leaned over the table. Karen had a great ass. At times he would get behind her and hold the pool stick with her showing her how best to make the shot. She was laughing and giggling a lot. I think he knew she was buzzed. As the night progressed, he was pressing up more often “helping her” and Karen didn’t seem to mind. I was getting comfortable on the couch to the point where I started to close my eyes. I heard Mr. D say to Karen, look Kat is already sleeping. I wasn’t, but I just kept my eyes closed. I just thought it was fun to fool them. He asked her if she was hungry and she said yes, so they went upstairs to the kitchen. As they passed me he said “shhh, she is sleeping” as they both tried to be quiet. I could hear them in the kitchen. After a few minutes, I heard them leave the kitchen. I quietly made my way up the stairs. I wanted to spy on them. I think it was just the booze and pot that made me act this way. They were in the living room and I could hear them talking. He started off be asking her how old she was.
“Seventeen” was her reply.
He said, “I can tell you have been smoking pot”.
“Just a little”, she said.
“Do you have any more on you?”
She said, “yeah, why?”
“I wouldn’t mind a little myself”.
She said, “I’ll go get it, it is downstairs in my purse”.
“Well don’t wake me up Katherine”, he said.
I quickly went downstairs and pretended to be sleeping. Karen got her purse and was trying to be as quiet as possible as she headed back up the stairs. Once I knew it was safe, I quickly went back up the stairs to spy on them. I thought it was funny. They were in his living room and they were smoking. I heard him inhaling, holding it in and then exhaling. Then he said so you want a hit yourself. Of course she said yes.
“I like your outfit, you are a little hottie” said Mr D.
“Thank you”, Karen replied.
I couldn’t see them but I could hear everything they were talking about.
He said, “I see you have a nice little cameltoe”.
“Cameltoe?”, she repeated puzzled. I was thinking the same thing. What the heck is he talking about, I wondered.
“I don’t know what you mean? Cameltoe?”. And I guess she thought it was funny and she started to laugh.
He said, “that’s what’s it’s called when a girl wears tight pants like you are and you can see her pussy through her pants”.
“Oh is that what you call it”, she said mockingly. That must be an old guy thing”, as she laughed. “Besides you shouldn’t be looking”.
“Isn’t that why you dress that way so the boys look at you”, he came back with.
“I dress this way because it is the fashion”, was her response..
“I think you are a little cock tease”, he said laughing.
“I am not a cock tease, I have done stuff”, she said defensively.
“Oh you have. What have you done?”, said Mr. D.
“You know… stuff,”, she said.
“Have you sucked cock?”
“Yes”
“Have you been fucked?”
“Yes”
“A lot?”
“A few times”, she responded.
“Ok, I take it back so maybe you aren’t a little cock tease. I guess you are more of a party girl then”.
“Yeah, I am a party girl”, she said proudly.
“So you like to have fun then?” he said coyly.
“I guess you can say I am a-venturous”, she laughed at herself slurring the word.
“He said I like girls that are a-venturous”, as they both laughed.
“You know sweetie, pot makes me horny, how about you?”
“A little… I guess”, she said reluctantly.
“Well since we are both horny, maybe we should do something about it”.
“But you are like my father’s age”
“Kat doesn’t seem to mind my age. Did she tell you I fucked her?” I couldn’t believe he told her.
“No, she didn’t tell me that. You’re just saying that”, she said doubting him.
“No really, I did. Ask her about it later. I am totally serious”
“Wow, so…she did it with you huh…. Cool”
“Oh yeah, so have you ever fucked an older man, Karen?”
“Kind of…he was a college guy.”
“How old were you?”
“16”
“So I guess you were a virgin then?”
“Yes”
“Ok, so I guess you are a little a-venturous”…he was playfully teasing her.
“A little?, she questioned. I even fucked a guy I meet at a concert, right in the parking lot, right in his van. He was like 30”.
“You did?, well I guess that is an accomplishment. So did he do you good?”
“It was….ok”
“Just ok?? Why, just ok?”
“It was kind of fast. You know what I mean?”
“So he came too quickly for you? So I guess you like a nice long fuck then?”
“Yeah, but I shouldn’t be telling you all this”, Karen said realizing she was being a little too open.
“Why? Because you are getting horny aren’t you? It’s ok sweetie. Tell you what, you can ask me any question”.
“Anything?”
“Sure”
“So you and Kat really did it?’
“Yep but I told you that already.”
“Did she like it?”
“Oh yes she loved it. Let’s just say I don’t come too quickly”, he said confidently.
“Why don’t you find out for yourself, how about it little Miss a-venturous?
“I don’t know….”
“Let me ask you another question Karen, have you ever had a big cock?”
“No”
“Ever seen one?”
“No, why do you have one?”, Karen said curiously.
“How can you call yourself an a-venturous girl if you haven’t even seen a big cock? Let me help you.”
I couldn’t believe what I was hearing. It was fun listening though.
“Oh my god, your cock is really big”
I was trying to visualize what was going on as I was listening.
“Is that all you are going to do is look? Come over here sweetie”.
I heard him pat the couch.
“I am sure an a-venturous girl like you needs to get a closer look”.
The next thing I heard was Mr. D. say “good girl”. Then he said let’s make this a little easier. He threw his shoes and socks to the side of the room I could see if I stuck my head out a little.
“What are you doing?”, Karen wondered.
“Just getting comfortable, that’s not a problem for you is it sweetie? I just thought you would want a better look.”
“Oh, ok”, said Karen.
Then he threw his shirt, pants and boxers. I knew he was naked.
“Why don’t you get on your knees in front of me sweetie, so you can get a good view.”
“Mmmm” that a girl”, I heard him say.
After a minute or so, he said, “See what you are doing to me. Why don’t you show me how you suck cock.”
“Ohhh that feels great….Ohhh yeah Karen. I can tell you have done this before”.
“Oh my god she is blowing Mr. D. I thought to myself. At this point, I had my hand under my skirt. It was very exciting hearing and trying to picture the scene.
I could hear her making sucking cock sounds.
“You’re a good little cock sucker. I can tell you have done this before Karen…mmmm…ohhh… yeah”.
“Lick my balls”, ohhhhh…. You’re a little slut aren’t you, you like sucking cock don’t you…”
There were no words spoken for a while. All I hear were sounds of oral sex and occasional sounds of pleasure from Mr. D. I was still touching myself. I was rubbing myself through my pantyhose and panties. It was so hot listening to them.
“Mmmm…you are gonna make me cum soon sweetie”.
A minutes or two later I heard. “Open your mouth..OHHHHH….oh yeah…..” I could tell Mr. D was cumming. I heard Karen walking then I heard water running. I went back downstairs so I wouldn’t get caught. I went back to the couch downstairs and thought to myself Karen must have let him cum in her mouth, WOW!!! A few minutes later, I could hear them in the kitchen. I thought they would come back downstairs but they didn’t. I waited another 10 minutes but they still hadn’t come down so I slowly and quietly made my way back upstairs. They were still in the living room. I could still see Mr. D’s clothes on the ground so I knew he was naked. Then to the right, I saw Karen’s red sweater and a red bra thrown on a chair.
She is half naked I thought to myself. This could be interesting. I wished I could see.
“I told you I am not a tease”, I heard Karen say.
“Sweetie, until you take off those pants, you are a tease. Girls go topless on the beach in Europe all the time”.
“You just want to see me naked. You’re just a dirty old man”.
“Yes and you are just an a-venturous girl”. Karen started laughing.
Karen walked over by the chair. I could see her from an angle. She didn’t see me. She was facing him. She had a pale complexion much like me. I couldn’t help but notice she had nice tits.
Karen sat in the chair and took off her red pumps. She stood back up. I can tell she was looking right at him. She was careful to slowly wiggle out of her white spandex while keeping her white panties on. All the time she was looking at him. “Well what do you think?”, she said. She put her hands on her hips like a model would and then she turned around.
“Am I hot?”, she said playfully. I guess it is only fair I get naked since you are.”
Then she slowly took off her panties as she continued to look at him. She put lowered her hand and I could tell she was rubbing her pussy. “I’m really horny Mr. D’Angelo”.
“Well then bring that bald little pussy over here”
She walked in his direction and out of my view. The next sound I heard was her saying oh that feels good. I started to rub my own pussy under my dress. I couldn’t tell exactly what was going on. All I would hear is a sound and my mind would create he image. This was so exciting. I found out later on the way home that he started by fingering her but quickly went down on her.
I was able to tell that he was going down on her. I heard her moaning, I heard her ohhhing and ahhhing. I was touching myself I was squeezing my breasts. It was hot. I was hot. After a while I heard her have an orgasm. OHHH…OHHH…mmmmm….Oooooooh…
“Not bad for an old man huh”, he said.
“Mmmmm…not bad at all”, she said satisfied.
“Let me move this table out of our way”, said Mr D.
‘Are you going to fuck me now?”
“Do you want me to sweetie?”
“Yeah but you can’t cum inside me ok”.
I was hoping she would fuck him. I wanted to hear that.
“I won’t sweetie. I need you to suck on my cock a little first”.
“Ok”
I could tell she was sucking on his cock.
“Mmmm….that’s a good girl, show me how much you can take in your mouth. Ohhhhh yeah”
“Ok sweetie that’s good. I’m going fuck you doggy style now, ok?
“Ok”
Right then I slipped my hands into my panties.
Aaaaaahhh…..ahhhhhh……..ahhhhhh….oh it’s so big, I heard Karen say.
I knew how she felt. I knew that once she got use to it she would love it.
Ohhhh..mmmmmmmm……..ohhhh
I had to see what was happening so I slowly moved to where I could look into the room. Slowly I stuck my head out to peek. Mr. D. was kneeling behind Karen. Karen was on her knees on the floor with her arms and head on the couch. Her back was arched upwards, her butt was in the air. Mr. D. was holding his cock as he was slowly entering her. At that moment I wished I was in her position. I wish I was the one being fucked by that big hard fat cock. This was perfect, they couldn’t see me but I could watch them.
Mr. D was slowly inching in to her. He now had both hands on her hips.
“Ohhhhh, fuck”, Karen said.
He was being very gentle with her as he was with me. I guess he knew a cock like his took some getting used to.
“You ok sweetie”, he said.
“A-huh”, was her response.
And with that Mr. D held onto her hips and began fucking her slowly.
Karen was very “vocal”. She was what I later learned was a moaner/screamer.
“Ohhhh….ahhhhh..ummmmm”….sounds were all involved.
After Mr. D. started picking up the pace it didn’t take long before Karen had an orgasm…
Mr. D. pulled out and started to re-position her. I didn’t want to get caught watching and I needed some relief myself. It was so hot watching them both. I went back downstairs and lay on the sofa. I turned down the volume on the TV so I could still here Karen in the distance. I pulled down my pantyhose and panties and began rubbing my clit with a sense of urgency. Then I finger fucked myself using 2 fingers and pretending it was me being fucked by Mr. D. It didn’t take me long before I gave myself a very much needed orgasm. I collected myself and went back to hear what was going on upstairs.
“You like fucking this dirty old man don’t you?”
“Mmmm yes was her response.
OHHHHHH….OHHHHHH…..OHHHH fuck I am cumming again I heard her say…..Oh…oh..oh…oh….OHHHHHHH
A couple minutes later I heard Mr. D say, “Ok Sweety, my turn”. Oh yeah, that’s a good girl. Ohhhh…ohhhhh…..
I went back downstairs. About 10 minutes later they both came downstairs. Mr. D said look she is still sleeping. Karen came over and woke me up. We ended up leaving a few minutes later. I asked Karen so what did you end up doing while I was sleeping. She said well you aren’t going to believe this but I fucked Mr. D’Angelo and I know you did too. He told me you did. I ended up confessing to her that I had. She wanted to know all the details and I wanted to know all her details. We agreed to tell each other what happened as we drove home. I didn’t tell her I was listening in or that I watched. I didn’t want to embarrass her. As you can imagine the first thing out of her mouth was, doesn’t he have a really big cock.