I think I have a pretty interesting sex life and decided to write about it. The story has a lot of my thoughts and may be slow moving for some.
A little bit about me. I got the idea to write this from an old picture of me winning my award which is detailed in the story. Background; My father was not very nice. I hated him he was verbally and physical abusive. He would always put me down. As a result, as a kid, I was not very confident and I was very shy. Kids made fun of me. I wasn’t an attractive little girl. I was always ashamed of my body and tried to cover up my body. This story takes place when I was eighteen back in 1987. Back then I thought I was too heavy but looking back I had a great body. I was na? and I was withdrawn. I looked down avoiding eye contact when I walked through the halls of work. I was soft spoken. I was polite and I was proper. I usually dressed to hide my breasts as I was self conscious about them. I was a size 3 or 5 depending on the dress. I was 5’2” and weighed 95 lbs with 34DD breasts. Everyone always said I had a model’s face and that I looked innocent.
Mr. D’Angelo was the director of the department I worked for. I was working for the company for two weeks when I was told to go to his office one day because he wanted to talk to me about career opportunities. He told me that although I got hired, the first 6 months were really a trial period where I would be evaluated. He said so far I have been doing well. He asked me what I would like to do. I didn’t know how to respond I just said “I don’t know yet.” He asked me if I wanted to make a career there. I said that I wanted to eventually move up in the company. Then he asked if I was going back to school. I told him I wasn’t planning on going back to school as my high school grades were not that good. He told me it would be hard to get promotions without additional schooling. He said he wanted to continue our discussion but that he had meetings the rest of the day. He said well since it is almost lunch time how about I treat you to lunch and we can continue the discussion. I said ok I just have to go get my coat. He said his car was right outside the building and that we better just get going as he was in a hurry. He drove a big Cadillac with a big bench front seat. As we were driving, he told me I was a very pretty girl and he was curious as to why I would to work at this place. I told him that I heard from my father that it was a good company with good benefits. I was trying my best to sound “adult”. I just knew it beat working at the supermarket. Most of the time, I had very little to do. There was more small talk before we reached the restaurant. It was an expensive Italian place. Even though there were parking spaces by the front, he parked in the rear of the lot. I thought that was a little strange. We walked in and the person that seated us knew his name which as I remember impressed me. I ended up ordering chicken parmesan. I wasn’t too cultured in eating out at a fancy restaurant. Mr. D’Angelo ordered a bottle of wine as soon as we sat down. I knew that he knew I was only 18. So even though I wasn’t legally supposed to drink, I didn’t say anything as the waiter poured my glass. He said, “Katherine I can’t help but notice that you are very quiet, are you nervous?’”. “Maybe a little bit” I said. He asked me if I was the shy type. I said I am a little shy at first with people until I get to know them (which was a little bit of a stretch, I was shy). He said you don’t have to be nervous around me and said he thought my shyness was very sexy. I smiled nervously looking away not knowing how to acknowledge what he said. While we were eating he told me about a couple other girls that had worked for him that started in a similar situation as me and now they are in management making good money. I said, hopefully I can do the same. He said it takes hard work plus doing above and beyond in order to separate myself from everyone else. He said those girls did that. Then he asked me if that is what I wanted. I said, “Yes Mr. D’Angelo”, thinking to myself who wouldn’t want that. He said that’s good Katherine. I hated being called that, so I said you can call me Kat if you like Mr. D’Angelo. He said, “Ok Kat, that name suites you better”. We finished lunch, I ate like a bird back then and only finished ½ my meal but I did manage to finish 2 1/2 glasses of wine. When we got outside the cold air hit me and I felt a little drunk. Not being use to drinking and weighing only 95 lbs….well you get the picture. When we got back to the car, he didn’t start the car right away but instead continued talking. He said, “Kat, you seem like a very smart girl, the kind of girl that wants to succeed, am I right?” “Yes” as I nodded. “Do you want my help?” Sure, I said. He said “well then maybe we can help each other, ok?” I said ok but I am not sure how I can help you. He said well…I can think of a couple ways…and with that, he just looked down at my breasts. I glanced down and realized my nipples were showing through my white blouse so I crossed my arms covering myself up. I was caught off guard and did not know how to react to him staring at my chest. As a result I didn’t say anything.
He said, “Don’t be so shy. So are you ok with that?”
I said naively, “with what?”
“With helping each other. You want a career and I’ll help you. In return all I want is a little bit of …fun…excitement.”
I looked away. I was still thinking about what he was saying, “What kind of fun and excitement?”
He said, “You are a very pretty girl with a great figure… let’s just say, I really like shy, pretty young girls with hot little bodies”. I looked away and was blushing. He leaned over to me in a half whisper and added, “With nice tits”. He continued, “See, you are shy, you’re blushing as he put his right hand on my knee. You don’t even know what to say”.
I said “Thanks, as I smiled nervously back at him. “Good”, he said as he started to move his hand up and down on my leg then he squeezed my leg right above my knees a few times as he leaned into me. “Fun for me would be to feel those nice tits.” That’s not too much to ask for, is it Kat? Don’t you have to get back for your meeting?, I quickly said trying to change the subject.
“We will have to make it a quick feel then won’t we, Ok, Kat?” I actually was a little relieved at that point since all he wanted was a “quick feel” plus I was a little wasted.
“Ok, Kat?” he said again.
“Ok”, I meekly replied.
Then his hand left hand reached for right breast. He firmly squeezed my boob. Then he gently moved his hand over my breasts rubbing lightly and focusing on my protruding nipples. His finger circled then pinched my nipple. Then he pinched a little harder. He would squeeze using his whole hand and he was alternating rubbing, squeezing, pinching and pulling.
You have really nice tits, they seem so firm, he whispered in my ear. Are they Kat?
“Yeah”, I said very softly.
“I want to see for myself, ok?”
Here? Right now? as I looked around. I don’t know… He already had opened the 1st button.
We had a deal Kat, right?
Before I could respond the 2nd button was opened. I shook my head yes. Then the 3rd button.
“You have a beautiful cleavage. So round so perfect…I love lacy bras”.
He moved the left strap off my shoulder then the right. I slipped down in the seat in case anyone walked by.
Then he pulled my bra down as both breasts popped out.
“Oh Kat they are so perfect”…then his hand was on my left breast. He squeezed…”ummmm so firm, you are right Kat. I thought they would be perfect and they are.”
Thanks Mr. D’Angelo.
What he did before on the outside of my blouse he did again: alternating rubbing, squeezing, pinching and pulling on my nipples. …mmmm…..was my response, as it felt good.
“You like that Kat?”
“Then you will like this even better.”
He started gently and slowly circling my nipples with his tongue, he knew what he was doing and it was driving my wild and he knew it.
Mmmmm, as I moaned a little louder. I closed my eyes…..mmm. He would alternate breasts. Then started to suck on them and when he lightly bit on my nipple…ohhhh. Then all of a sudden I felt his hand on my leg, rubbing up and down. He was still nibbling on my nipples. I felt his hand go under my skirt. Even though his sucking on my breasts felt so good, I was thinking about his hand. I had the presence of mind to ask shouldn’t we get back to work Mr. D’Angelo?
“Don’t worry Kat in a few more minutes”.
Ok, we were almost done I reasoned. His hand was moving higher up on my inner thigh as I squeezed my legs together hoping he would retreat. He didn’t.
“Kat don’t be nervous”
“but Mr. D’Angelo, I shouldn’t be doing this with you”.
It’s ok, now relax…as I did his hand slide upwards…he was now rubbing his right hand on my pussy through my pantyhose and panties. He applied just enough pressure and motion. “mmm” See Kat, this isn’t so bad now is it?”
”No”…between his mouth and his hands I was feeling good…
“Feels good Kat?”
Yes… I knew I had a kind of buffer zone as I was wearing pantyhose and panties. I figured he wouldn’t go any further and he didn’t….as he continued to rub me…”mmmmm”…..”ahhh” was all I could say…
He abruptly stopped as he said we better get back to work now. I fixed my skirt, adjusted my bra and started buttoning up my blouse and sitting up. As we drove back to work he said “See Kat you helped me out and now I will help you out. Kat next Friday is the company Christmas party, were you planning on going?
“I don’t think so, I heard it is mostly older people and I still don’t know that many people here”.
“He said, well I’d like you to go it would be good if you did. Just put on a pretty dress. You’ll have fun. I’ll even sneak you a few drinks”.
Ok, Mr. D’Angelo that would be great. Neither one of us spoke until we were back at work.
A couple days later I won an award. Along with the award came a $100.00 check. My immediate supervisor nominated me but I wondered if Mr. D’Angelo had something to do with it.
I did go to the Christmas Party. My mother went to the store with me and picked out a long black dress with shoulders and a slit down the side. My mother always picked out dresses and outfits that highlighted my figure where I tended to shy away from clothes like that. She was my mom and had good taste so I took her advice. I would wear all black from my high heel shoes to my bra, panties and pantyhose. The night of the affair, my pantyhose ripped as I was getting dressed. I asked my mom if she had anything and she came back with a pair of thigh high black stockings. So I wore those. When I left my house my mom said “Katherine you will have to fight off all the men as she laughed and smiled at me. She wasn’t kidding. When I got there I had no problems finding people to talk to all be it mostly older men. We have a big company so there were a lot of people at the party. I saw him across the room and he was talking to a group of the “big bosses” as we called them.
It was crowded but then I finally saw him later by the bar. I didn’t have the nerve to talk to him. I sat down next to a small table. He walked over and put a drink of orange juice and vodka next to me and said here you go and walked away. That happened a few times during the night. A also got a drink from another guy that was there. So I had a few drinks that night. At one point Mr. D’Angelo walked up to me and said “Kat I need to see you later, I have something I need to discuss with you, meet me out front in 20 minutes”
I wasn’t 100% sure what to expect. Was he going to tell me it was a mistake and that we shouldn’t have. Did something happen? Did he really want to talk? Or did he want a repeat? If so, was that all I had to do, just let him touch me a little and he would help me or would he want to do more. He was an older man, older than my parents. I was nervous but excited trying to think about what was going to happen.
So when the 20 minutes went by I went out front. Even though it was early December it wasn’t all that cold but cold enough. After a few minutes I heard a beep and looked and saw it was his car. He waved and in my high heels I slowly walked down the little hill towards his car. He pulled out of his spot and drove around and picked me up. I slowly stepped into his car keeping my dress in order. His car was nice and warm. He said it wouldn’t look good if people saw us together. He said it would be hard for him to help me if that were to happen. I understood. I said we didn’t have to talk, I don’t want to get you in trouble or anything. He said no it’s ok we just have to be careful. He said I don’t have too much time as I have to get back home to my wife before it is too late. He drove out of the parking lot. I said where are you going? He said just around the corner where we can have a little privacy.
My mind was thinking about all the different things that could happen. He is married so maybe he really does just want to talk. He pulled in to a side street and parked away from the houses. He turned the car off and told me that I look beautiful. “You are the sexist girl in the room”. I said thank you, I really did consider that a compliment because there was a lot of beautiful women there. I said you look very nice too as I thought it was polite to return the compliment. That is when I realized the situation, his suit jacket was off we were on a quiet street. That is when I figured out that by talking about my career he meant a repeat of last time I reasoned. I could do that with him again, I was trying to talk myself into it.
He said so I see you got a $100.00 award, very good… I said that was you right? Me?? Smiling he said, “I am sure you earned it”.
Maybe we were just going to talk, I thought to myself.
Yeah, I guess so I worked hard finishing up all the reports on time, not realizing what he meant by earning it (as I said I was naive). He said so you still want my help?, as he slide closer to me. Yeah I said nervously thinking about what that answer may mean. He said “Well prove it”
“Prove it, how?? I said.
Well you can start by lowering that dress and letting me see those perfect tits of yours again.
Start?? What am I getting myself into? I just kind of froze for a second. I thought to myself last time wasn’t so bad.
He said turn around, and I did, as he undid the clasp on my dress and pulled the zipper down….in an instance he was undoing the clasp to my bra… I held it in place as he turned me around, he pulled my hands down and then pulled my dress down as my breasts sprung out. (I had perky breasts considering they were so big).
He said black looks good on you against your complexion, ( I am very white skinned.)… He just looked at them in the dim light for a few moments before he went right to work on them just like last time…. After just a few minutes, his mouth was on my nipples and I was mmming and ahhhhing. Even though my dress was long he had managed to get his hand under the slit part and was moving his hand up the inside of my leg. I instinctively squeezed my thighs together. “I don’t have much time Kat we did this last time so there is nothing to be nervous about, I am just going to touch you just like last time, ok?
“OK”, and I opened my legs and his hands moved upwards. I had forgotten that I wasn’t wearing my pantyhose until his hand was on my bare skin. Would he think I did that on purpose?
He stopped and rubbed the bare skin of my inner thigh. “Your skin is so soft.”
Then his hand went further reaching my panties. He was feeling the fabric, “satin” I love satin, are they black?
“Yes” I said wondering what he was going to do next to me.
Then he began rubbing me softly up and down and then in circles over my panties. He was still nibbling on my breats and he was so good at it… he was applying more pressure on my spot …mmm….ahhhh….as I unconsciously opened my legs a little wider. He bit down on my nipple. God it felt so good, feeling the simultaneous soft touch on my pussy through the material as his mouth was on my nipples…he began whispering in my ear. “You are so pretty. Do you like me rubbing your little slit through your panties?”
It feels good?
“I can tell you now, your panties are all moist”, he whispered.
”You want it to feel even better?”
Yeah… I was just caught up in the moment not really thinking about what he was asking me.
His hand worked its way into my panties.
What are you doing? We can’t…we shouldn’t…you’re married, as I pushed his hand away.
“Kat, don’t worry just for a second, ok?
He didn’t wait for a response. His hand was inside my panties and his finger found my spot. The same spot I touch when I am being naughty. I opened my legs a little wider.
“Good Girl” he whispered into my ear
He started kissing my neck and nibble on my ear lobe. His hand movements were slow and sensual. I could feel him lightly tracing my pussy lips.
Mmmm, as his hand moved up as he was lightly rubbing the hair above my pussy (I kept it trimmed short.)
“So soft Kat…so soft” His mouth found my nipple again. He was rubbing the outside of my pussy and it was driving me crazy. His finger was now inside my pussy lips.
Ohhhh. I heard myself say.
Whispering in my ear, “Your cunt is so soft and wet”
His finger found my clit as my legs nervously twitched. Circling…mmmm. He started rubbing a little harder on my clit…he knew my spot.
My eyes were closed, I was enjoying it. “Ooohhh, Mr D’Angelo, it feels sooo good.
“Your panties are in the way” As he reached under my dress with both hands. I lifted my butt up so he could take them off.
His hand went right back to my pussy. He was slowly circling my clit…..oohhh…then up and down…circling…..up and down…nibbling on my ear….mmmmmm…
“Should I stop now?”
“No, don’t stop, I replied”.
Next his finger was circling at my opening as he was applying light pressure. He would go back and forth between my clit and my opening.
….ooohhhh…..ahhhh as my breathing quickened…
”You aren’t a virgin are you?
He pushed his finger deep inside me….ohhhhh….his finger was slowly going in and out. “I love your tight little pussy, it is so tight….
Then he quicken the pace as his finger began fucking me…..ohhhh
Mr. D”Angelo, please stop. I had given myself orgasms but I didn’t want to have one in front of him. “I’ll stop after you cum. Cum for me Kat”
Sensing I was getting close to an orgasm he switched back to my clit and moving his fingers back and forth at a quick pace. I began to breath heavy in short doses.
Cum for me Kat, cum….
OHHH!!!, AHHHH!! OHHHHHHH as my body quivered…OHHHHHHH...I had my 1st orgasm by a man….
After I came back down to earth, I was embarrassed that I had been so loud. I didn’t know where to look. He handed me my panties as I was fixing my bra. I took off my shoes, stepped into my panties and fixed my dress. He sat up and put his finger in his mouth tasting me….
”mmmmm,so sweet”he said as I looked away from being embarrassed.
“Well, I have to get back to the party, he said”.
See Part 2 for the rest of this true story.