I made it to Friday, and I locked up my desk and went to my car. I saw an envelope on my windshield. I was tempted to throw it away. I got in the car and opened the letter on pink paper. I started to read, "Dear Pretty Boy, well, you made it to the end of the week I know you have been trying to figure out where all of this is going."
I paused to weigh my options, but nothing was attractive. I read further, "Zak, I want to explain to you what I am doing not through letters, but in person. I am going to send a limo to your house tonight at 7:00 pm. After we meet you can decide for yourself if you want to continue this journey. I have no intention of doing anything that will cause any embarrassment. I need for you to hear me out. I have been attracted to you since I first saw you at the gym. I will see you tonight. Love You."
Now, my mind was going into overdrive. I had two hours to think about the situation. I was going to suck it up and face my fears. Up to this point, I did not know if the person was male or female - not that I cared. I made my way home to shower and change clothes. I was getting nervous as the hands on the clock ticked away. As the time rolled to 6:45 I got lightheaded. I started walking towards my front door and stepped outside. I thought, "Zak what hell are you doing?"
At seven o'clock a black limo pulled up and I hesitated. I got in the back seat; there was a bottle of champagne, so I thought I might as well enjoy myself. It took forty-five minutes to reach the destination. The limo pulled up the driveway to a single-family home. I exited and walk up to the door. There was a sign on the door for me to enter.
I walked through the door and I detected a sweet scent. I took a seat in the living room. I did hear a noise in the other room and then, "I'll be right with you, Zak." I was trying to process the voice and realized that it was Kristen from work. When Kristen walked into the room I froze.
Kristen looked at me and smiled. "Zak, are you surprised?"
I hesitated and stubbled my words out, "Kristen, you look beautiful." Kristen is 5'9'' tall, 115 pounds with slender, well-defined legs and ample breasts. She would turn every head in the gym, both male and female. She had on black stockings, a short red skirt and a white blouse. I had to stand back and take the view in.
Kristen walked closer and kissed me; her lips were soft. I felt her tongue enter my mouth and our tongues played.
Kristen stepped back, "Now, that was not so bad now, was it? Oh, before you sit down can you remove your clothes except for your panties. I just want you to be comfortable and I will explain."
Kristen walked closer and started to unbutton her blouse, which revealed a lace push up bra, which showed her beautiful breasts. She unzipped her skirt and let it fall to the floor. My eyes were on her sexy body wearing a garter belt with matching panties. Looking closer, I saw she had a shaved pubic area. I could see the beautiful outline of her vagina. She looked delicious.
As I started to get comfortable, my dick was growing. I was having sexual thoughts. I was open to whatever was going to follow. I looked. "Oh my God, Kristen, I can't get over how beautiful you look, so excuse me for staring."
Kristen came over and sat down and had my full attention as she spoke, "I can only imagine what you have been thinking trying to figure out who was stalking you and saw you in your glory."
I was going crazy because I really did not know what to do, and wondered if my life would be ruined.
Kristen continued, "What were you thinking when the guy in the gym was playing with his dick?
I'd thought he was the person sending the letters. As he was rubbing his dick, I knew it was not him. I was waiting for him to jack off and cum on the floor. He did have a pretty dick with a well-shaped head for sucking. He could not see how my dick was growing.
Kristen said, "I had asked him to do me a favor just to see what effect it would have on you.”
"He told me he was getting worked up a little himself and it was on his mind all the way home. Once he got home, he went upstairs and stripped and got some oil and stood in front of the mirror and gave his dick a good workout and cum was squirting all over. The session was intense like he never had before.”
“You see, you move people and that's what attracted me to you,” said Kristen.
Kristen looked at me, "I hope that after I tell you that you do not get up and walk away. I had been watching that pretty ass of yours at the gym for months and could not get you out of my mind. The day I saw you and the other guy I was jealous. I was watching the way you were looking at his dick. I was waiting for you grab his dick and give him a handjob, so I decided to keep my eye on both of you.
"How did you see us? I thought the door was locked."
Kristen responded, "The door on that room is tricky, you have to pull it hard to latch. When I did not hear it click, it was my chance to see what you two dirty little boys were going to do. I had no idea on what I was going to see."
I was engrossed in the moment and would not have stopped if anyone came into the room. When Louis had his dick in my ass I was in another place. To give you an idea, it is like putting some oil in your left hand and make a fist. Take your right index finger and push your finger through. You can imagine your fist is your anal opening and your index finger is a dick. You feel every inch as you push. The way your closed fist grips the index finger is the anal muscle gripping the hard dick. What a rush!
Kristen said, "I was jealous that he was enjoying you. When I saw him slide his slick dick in your ass I almost screamed as it looked so beautiful. He took his time to enjoy the moment as you were moaning. I watched as he pulled his dick out and then pushed it back in. It took my breath away. The way his arms wrapped around you looked sexy. My pussy got so wet the juice was running down my leg. I slipped two fingers in and I started getting myself off. I had never seen two guys fuck. You kept pushing your hips back to meet each of his thrusts. I was thinking about what you were feeling."
I reached over and took Kristen's hand to let her know that I was not upset. "Initially, I was scared. Now, I am open to whatever you have in mind. I am anxious to hear what is inside your head."
Kristen got quiet and her eyes moved away from me. I looked over and said, "I want you to look me in the eyes."
Kristen turned her head, "Just bear with me, this is not easy and don't judge me. I have been scared of doing this. I almost stopped; this is not in my character. You do not know what it took for me to dress like this. Once I was dressed, I felt sexy."
"I can say you outdid yourself and you look beautiful. Yes, you do have me sexually aroused."
"Zak, you come across as self-confident and I am the opposite and I hope that some of you can rub off on me. You think I have a lot of guys after me, but I do not. I stay off to myself and do not go out. Don't laugh, but when I saw you, I felt like pushing my fingers in my pussy and masturbating. I thought it was dirty to masturbate and a person had to be sick," stated Kirsten.
"Oh my, you poor baby you are so far from the truth. What you do with your body is all about you and if it makes you feel good who gives a damn of what other people say. How did you feel after you masturbated?"
"Well, it really did feel good and it made me realize what I have been missing," stated Kirsten.
I love to masturbate, and having my dick limp and putting the oil on it and rubbing until it gets hard. I like playing with the head and when it is time to cum, my God… what a feeling, and I wish it could last longer.
Kristen continued, "Ever since I saw you, I have been horny to the point it has been hard to work and before I know it my panties are wet. I take an extra pair to work. I was in the shower at the gym and found myself looking at other girls. Some of them had nice tits and clean-shaven pubic areas and I decided to shave mine. After I shaved it, I felt fantastic but no one to show it to. Two days later at the gym, a girl remarked, "Hey, you lost something". I looked at her and she was pointing to my pussy. I got a warm feeling and she was smiling at me. She came closer and brushed her hand across my mound and said how smooth it felt. There was a jolt and I tried not to show any reaction. All I said was thank you."
"Sounds like you have lived a sheltered life; my place will be to help you to explore whatever you want. The guideline will be not to do anything which you are not comfortable in doing. It could be things like oral sex, masturbation, both self and mutual, anal sex, lesbianism, and watching pornography. I hope you don't want me to write out a lesson plan." I was looking at Kristen and tears were rolling down her cheeks.
Kristen hugged me. "I never had anyone who wanted to listen to me. You are making me feel good about myself already. What you said, it all sounds good and I want to. I hope you don't think there is something wrong with me."
Kristen looked at me and said, "I want to see you jack off. You were enjoying your friend’s dick in the room.”
"I will masturbate, and I did enjoy playing with Louis. I fell in love with my dick at an early age. The only bad thing, it does not stay hard long. Do you have some oil that I can use?"
Kristen said, "Let me get the oil and towel. I think after a week you might make a mess. Oh, you did not jack off all week, right?"
As Kristen came back into the room I had her stand in front of me. I was looking up and down her body, first her tits and how full they looked in her bra and along her hips and the top of her panties. I looked down at her long legs and stockings. Kristen was watching my dick as it began to grow.
"See what you are doing to me? I am getting excited just being near you."
I took her hands and placed one at the top of my panties and asked her to remove them. Slowly she pulled them down as my dick bounced free. Once I had them off, I took her hand and placed it on my dick.
Kristen said, "Your dick feels so good. Oh my… so smooth. This is my first time holding a hard dick. What do I do?"
I said, “Just wrap your hand around it and go back and forth real slow."
I asked her what was wrong. I pointed to her panties and there was a large wet spot where her pussy was dripping. She only smiled.
"Looks like your pussy is getting hot, Kristen." She stepped back and took a seat.
Kristen said, "Zak I want to see a real dick shooting cum out of the tip. I was at work in the bathroom stall and two girls came in and one was talking about her boyfriend and how she watched him jack off and was shooting cum all over her tits and how wonderful it looked. I won't tell you what I did."
I had Kristen sit down and I walked in front of her. I held my dick and applied some oil. I wrapped my left hand around my dick and massaged it by letting my hand go back and forth. Kristen had her eyes focused on my dick.
I said, “Kristen… breathe!” She looked like she was in a trance.
Kristen spoke, "Oh yeah. It looks so... so... wonderful. It looks like it is so much fun, and I wonder what it would be like walking around with something like that hanging between my legs? Do it, Zak, keep it up. I want to see you cum."
Kristen picked up her phone, "I need a picture so when I get bored, I'll have my private show. What a pretty dick... jack it off, baby."
"Oh, Kristen, this is more intense because you are looking at me. I am usually in front of a mirror. Sometimes I am up against a wall and when I cum I squirt in my mouth, but that is another session. There is an art to jacking off and you never rush it."
Kristen reached out and started rubbing my balls. "Go ahead, grab my dick and you do it."
Kristen said, "Oh, it's hard… It feels strange in my hand. This is so nasty, she giggles. I want to see your cum.".
Kristen releases my dick and I squeeze the head and a drop of lubricant was at the tip, and she reached out to remove it so she could taste it.
Kristen said, "Ummm salty and sticky."
"Kristen, remove your bra. I am getting ready to cum on your pretty tits." I start to increase my pace and Kristen is watching my balls draw up tight. I can feel the tingling up through my legs. "You had me go a week without jacking off and my cum is backed up. Oh, baby. I want to explode all over your tits... yes! Yes!"
Kristen said, "Zak... do it, baby… shoot your cum all over my tits, baby. I am ready for your sticky stuff now.”
My legs were shaking. "Oh damn… Kristen, baby… I am cummminngg so hard! Yes… look, baby." There were four strong spurts which shot from my dick right onto her tits.
Kristen screamed, “Oh Zak... fuck... look at it."
Kristen looked down and both of her tits were dripping with cum. She stood up and moved closer and scooped some cum and rubbed it on my lips. She hugged me tight and we kissed, both tasting my cum.
Kristen spoke, "Zak you do taste good and maybe next time I can get closer and suck your dick with your cum shooting out."
I looked at Kristen. “You are a naughty girl.”
Kristen said, "That was so damn hot. Look, I have pussy juice going down my leg. I did not even touch myself. Wonderful, Zak."
I asked Kristen if this is what she had in mind.
Kristen responded, "Oh Zak, this was much more than what I had in mind.
"Guess we need to clean up."
Kristen looked at me, "You can bring some clothes over and stay a few days... or weeks."
"Okay, that sounds like a good plan. Off to the shower."