I met him when I was an eighteen year old temp just out of high school. He was the hottest and most sophisticated guy I had ever met. I wanted him to think of me as a mid-twenties sophisticated career girl and I think he did; until he entered me.
I had a two week assignment at his company while the regular secretary was away on vacation. He had a team of four employees plus the secretary I was temping for. The four other guys were all single and good looking, but my boss was hot and he was the one I really wanted. He was 25, owned his own company and had the self assurance and sophistication of a young and successful entrepreneur. I had never had any trouble getting asked out by guys I wanted to ask me out. I was a fox and I knew it. My long jet black hair, blue eyes, peaches and cream complexion, long legs and bigger than average bust never failed to get the attention I craved. I had had lots of boyfriends since I started dating and had done some very heavy petting, but was still a technically a virgin. I say technically because I had given oral sex to three of the guys I had dated in order to avoid having intercourse. In fact, I had become a truly great cock sucker in order to keep my virginity and I was proud of my skills in that department.
I started flirting with Ryan my first day on the job, but he was all business and remained so the entire two weeks I tempted for him. The other four members of his team were all great guys and really cute and after the first week of being totally ignored by their boss I began a joking flirtation with all of them and even hoped that any one of them would ask me out. I even wore some outfits that were a little over the top, but at the end of my second week, even though I had made it plain that I wouldn't mind seeing more of any of them; no one had asked me out or for my phone number even.
At 5:00 PM on my last day Ryan gave me my check, thanked me for the last two weeks and said, now that I was officially no longer an employee would I like to have dinner with him Saturday? I was stunned, but said yes.
The next day he picked me up in his Porsche and asked me how I felt about a rack of lamp with roasted potatoes and vegetables. I told him that I loved a good piece of meat and he laughed and said that he was happy I wasn't a vegetarian as he had spent the whole day cooking. When we left his car and got in the elevator he took out a card key that allowed access to the top floor of the apartment building. His apartment was the penthouse. While we were going up the elevator I made the decision that he would be my first and began to feel wet.
Dinner was accompanied by a really fine French wine. Dessert was crème brulee and coffee. Afterward we went into the living room and had a glass of port. After my second glass of port I was feeling very relaxed and very horny and was thinking about making the first move when Ryan leaned over and started kissing me. After about half an hour he had my silk blouse and bra off when I stood up and dropped my skirt around my feet and said to him lets go into the other room. He looked at me for a very long time and I had never felt so sexy in my life standing in front of him in white thigh highs, black pumps, a thong and nothing else. After what seemed like a few minutes he said, "Don't take the shoes and the stockings off, but let's lose the thong". My heart was beating a mile a minute, but I smiled and rolled my thong down and dropped it to the carpet and stepped out of it and stood nearly naked in front of him. I wanted him to think of me as a mid twenties sophisticated career girl, but standing nearly nude in front of him I felt like the eighteen year old virgin I was.
In the bedroom I undressed him and when I finally got my hand around his penis I was surprised at how big he was. I started by giving him my most expert head and I could tell by the wide eyed appreciative smile that he was impressed. Then he rolled me onto my back spread my legs open and began to guide his penis into me. I closed my eyes and clutched the bedspread with my hands. I did not want him to know he was my first, but after a few minutes it was obvious. My eyes were still shut, but I could feel the hesitation and his look of astonishment. He then withdrew and began to make love to me with his mouth. That lasted for about twenty minutes and now it was my turn to be impressed. By then I was totally wet and he slowly, ever so slowly, entered me. I gasped for air as the pressure grew inside me. Finally, I could feel that he was all the way inside me and I lay splayed on the bed afraid to move. My eyes were beginning to water, I was having difficulty getting my breath and I was afraid I would bite through my bottom lip. I could feel his eyes on me as he pulled back from me. Watching me as he slowly withdrew himself from me until just the very head of his penis was in, and then, ever so slowly, he began to reenter me until he was once again fully inside me. Then he repeated the slow withdrawal and the slow reentering of me again. After the third time I could feel myself rising off the bed to keep as much of his penis in me as possible when he began to withdraw. After a few more minutes my legs came up and encircled his and my hands clasped his ass as I began to moan and lift off the bed. I heard him chuckle and finally opened my eyes. He was staring into my eyes and I felt like a small helpless animal offering itself up as prey as I completely surrendered to my lust.
I had never had an orgasm, but now I could feel myself getting closer and closer to cumming. His rhythm increased and now he was easily filling me with each thrust and I could feel my vagina opening up to him more and more. Then I felt him expanding in me and cumming, but I wasn't ready. I pleaded with him not to stop. Not to leave me hanging like this, but I could feel him shrinking away and finally falling out of me. I began to plead with him do it to me again, but he laughed and said maybe in another hour. We cuddled for awhile and then I began to suck him back to hardness. I could feel him getting harder and harder and when I knew he was close to cumming I tried to stop, but he put his hands around my head and began to thrust into my mouth and before I could stop him and myself he was cumming into my mouth.
I began to cry in frustration. He said he was sorry, but I was just too good of a cock sucker and he had to cum in my mouth and that he was finished for the night. I told him he was a selfish bastard. That it wasn't fair to me to be left so turned on and horny. I told him that I felt like getting dressed and going to the nearest bar to find someone to take care of my needs. He just looked at me with a quizzical look on his face. Finally I said, "God I'm so horny I feel like I could just fuck all night long and you tell me you're done for the night…SHIT!"
Ryan looked at me and said, "Are you sure?"
I answered, "Sure about what?"
"About being able to fuck all night long"
"I've never been surer about anything in my life"
With that he said, "OK" and picked up the phone and hit one of the speed dial buttons.
I couldn't figure out what he was doing until I heard him say, "Todd, Ryan here. Call the rest of the guys and get over to my apartment pronto, I have an emergency on my hands" and hung-up.
I was stupefied.
I said, "Wait a minute…I'm not that kind of girl"
Ryan's response was, "And I'm not that kind of guy"
"What do you mean?" I asked.
"I mean I am not a selfish guy, I am going to see to it that you are taken care of. That all of your sexual needs will be more than satisfied by my team of guys. I am going to give you a night of sexual pleasure that you will never forget."
"But, I can't do …I'm not some slut that…my god you want me to …."
"I want you to enjoy yourself. I know that you find all of the guys attractive and they really like you as a person and think you are very attractive too. All of them wanted to ask you out, but I asked them to wait until you were no longer an employee and I could have an equal chance to ask you out."
I was speechless, but I knew that with every passing minute I was getting closer to a gangbang. Ryan leaned over and kissed me and said, "Honey relax, just enjoy yourself" and he began to kiss and caress me.
I knew that I wanted to do it, but I didn't want to be "that kind of girl" and I told him, "Ryan, I'm not that kind of girl". He laughed and said, "What is that kind of girl? I know that you were a virgin until an hour ago so of course I know that you have never done anything like this before, but doing something like this does not make you a 'bad girl'. It makes you an exciting uninhibited woman, the kind that men dream of being with".
The door bell rang and Ryan asked me, "Do you want me to let them in?"
I answered yes.