Harry and I had a sweet arrangement. We slept nude together every night and sucking each other was a ritual. Our secret was safe, and no one suspected anything, but a few rumors circulated. We did not go to the clubs or drink with the other guys.
There was one shocking day, and we were exposed. I was fully dressed and horny. My back was facing the door, and Harry was naked, holding me with my dress pulled up, His hard, oiled dick was sliding between my thighs and legs, and fucking away.
“Now fuck me, fuck me hard. Fuck me until you cum on my legs. Harry, I need to be fucked so bad. Yes, like that. That’s so good.”
“I am so close to cuming. Your thighs feel so soft against my dick, and it is tight.”
While Harry was fucking my thighs, he slipped an oiled finger between my cheeks and was playing with my puckered hole. The feeling was electric. I wanted him to push his finger deep. The feeling of his hard dick sliding between my thighs was juicy. He started to increase his pace.
“Honey, I want to feel your warm, creamy cum squirting down my legs. I can feel the head of your dick pulsating.”
“I am ready to explode.”
I did not hear the door open behind us.
“Oh. I am so sorry. I thought the room was empty. I am the maid, Maria.”
Maria stepped in quickly and closed the door. It was too late; Harry was shooting cum down my legs.
“Agghh, Oh yes. Fuck. I am ccuummiinngg.”
Harry’s dick was twitching, pumping out spurt after spurt of hot semen.
“I have never seen anything so sexy and nasty. You two look cute. I loved seeing you cum, that was amazing and so much. My pussy is wet. I will masturbate when I get home. Please, may I take a picture? One more thing, can I lick the cum off your legs? I love the taste of cum.”
“Yes, you can take the picture and lick the cum off my legs. Do not share the picture.”
“If you need anything from me while you are here, let me know. If you do this again, I would love to watch from the beginning.”
Maria took off her red panties and tossed them to me before leaving the room. They had a wet spot in the front.
“Kevin, how do we deal with this?”
“This does not change anything. It was exciting knowing that she loved watching us. I want to have her back. It may be kinky, but it is good.”
“I need some time to process this. If the word got out, we would be on the next flight home.”
After Maria left, we took a shower together and slept nude holder each other.
The next morning, there was a note under the door from Marie, “Text me your phone number.”
Harry was showing signs of concern about getting caught. I had to find a way to calm him down.
Later in the day, a text message came from Maria, “Now we are even. Love, Maria.” There was an attachment. I found myself starting. Maria had on a pink bra and a thong, standing with her legs spread. There were arms around her waist, and the hand was covering her pussy with a couple of fingers in her sweet spot. It was a female behind her.
Looking around, I spotted Harry and walked towards him.
“Now, do you feel better. I held the picture so he could see.”
“She looks beautiful. There was a lot she was hiding under her uniform.”
“You should feel better. She is not going to show the picture to anyone. I think we can have some nasty fun with her.”
“You have that look that makes me nervous.”
“Calm down. It will not be anything wild, but it will get your dick hard, lover.”
I knew how to control Harry. He loved it when I talked about sex and his hard dick and cuming. I wanted to give him a treat. When he was playing with my tight hole, I knew what he wanted to do.
There was another package from Pam. The excitement grew as I was trying to imagine the contents. There was a letter affixed to the box. I was eager to read it:
Dear Kendra
I want you to know I miss you so much. I wish that we had talked earlier about how you were feeling. We cannot make up for the lost time, but we can focus on the future. I will always be here for you.
Angela and I decided to send you another outfit. She has fallen in love with you and talks about you often. She wanted to know if you were still a virgin. Something has happened to her, and she wants to eat my pussy every day.
Enclosed, to celebrate, is a blue skirt and a white blouse, thigh-high stockings and a garter belt, a blue thong with a matching padded bra. Angela wore the thong.
You may send us a photo once you are dressed.
Love and Lust
Pam
I placed the box in the closet.
We had a three-day weekend coming up, and I wanted to plan something special. Harry had been dropping hints. He was showing more interest in my virgin opening. Each time he was sucking me off, he would play with my tight love-hole. It took me to a new sexual level, and it was exciting. His actions were causing me to think more about pleasing him. The last time I was close to the edge of wanting him to take my virginity. I wanted him to fuck me.
When I arrived at the hotel after work, Maria sat off in the corner. Maria waved to me to come over.
“Hi, Kevin. I want to know if you and Harry are free tomorrow night. I would like to have you over for dinner.”
“Sure, we can make it there.”
“If you have a few minutes to talk. When I walked in and saw you and Harry, I noticed you were wearing a dress. Is that what you enjoy doing?”
“Yes. It has been something that I enjoy doing. I like the way the clothes make me feel sexy.”
“How long have you been cross-dressing?”
“It started after I turned 18. I was wearing my sister’s clothes, and one day she caught me in her dress masturbating. She walked into the room as I was cumming. I was so embarrassed and thought she was going to tell our parents.”
“Did she tell on you?”
“Pam surprised me. She walked over to me and put her hand on my dick and squeezed my last drop of cum out and licked her fingers.”
“I was shocked and could not say anything. She told me that she knew I was wearing her clothes, and it got her excited. We had never done anything sexual, but it all changed after that day. She would dress up after school, and I would let her jack me off. I would cum on her tits. She had me eating my cum off her tits, and then we kissed.”
“You have a cool sister who loves her brother. Too bad she is not local; I would love to meet her. I want to ask you something personal. Have you lost your virginity to Harry?”
“No. He has not been inside me. I often think about it, and I know he wants it badly. He is always rubbing and playing with my tight hole. There are times I wish he would just stick his dick in me.”
“It sounds to me that you want it to happen. Let me propose that when you come to dinner, we plan to give Harry a treat.”
“What kind of treat do you have in mind?”
“You come to my place early for a makeover. I want to get you all prettied up. Getting fucked the first time must be special. There is one other thing. I want to make a video for you to remember.”
“You are getting me nervous. If that video landed in the wrong hands, we are dead.”
“There will only be one copy, and I will give it to you.”
“Why do you want to do this?”
“I am curious and want to see two guys fucking. I have seen videos, but I want to see them in person. I am kinky, okay. I like males and females. I will lick a pussy as fast as I will suck a dick. My pussy is getting wet talking about this.”
“Alright, I am open to it. The timing is right as I received another package from my sister, and it must be clothes.”
“You can bring the package, and we can open it together.”
“I will tell Harry about our dinner date, but not the details, and it will be a surprise.”
Maria looked at me and smiled.
“My sweet baby. I will take care of you like Pam. This will be your special night, and you can write Pam and tell her all about it.”
We stood up, and I watched Maria as she walked away. I went to find Harry and inform him about the evening plans. I could feel a wetness in my panties from my dripping fluid. Talking with Maria got me horny. I had a smile on my face.
“Hey, Kevin.”
I turned around, and it was Harry coming in the door.
I informed Harry about the plans for the evening, and Maria was planning something special. I knew that would make him excited. I told him to meet us in a couple of hours.
Before leaving the hotel, I returned to my room to get my package. Maria and I left for her house.
Once we arrived, she directed me to her bedroom.
“You can undress, and I will be right in. I must get you ready. We must remove all your body hair. You want to look pretty for Harry. Let’s go into the bathroom.”
We walked to the bathroom, and I was looking at my naked body in a full-length mirror. Maria began to remove her clothes, and I had a perfect view of her beautiful body. I was speechless, and my dick was showing excitement.
“Down, boy. We cannot have him getting in the way. If you need a hand, I can take care of that.”
Maria stepped behind me and reached around my waist. I felt her warm hand wrap around my dick, and she squeezed me.
“Oh my. Kevin, your dick feels good in my hand. It looks pretty, and your head is amazing.”
My mouth opened, but nothing came out, and I closed my eyes.
“Let me take care of my sweet girl. Maria will make your dick feel good. Keep your eyes closed and pretend that I am Pam. Yes, your sweet sister. Brother, I am going to stroke your dick until you give me what I want. Your cum tastes sweet, and I have missed the taste of your cum on my lips. I want to see you squirting your creamy cum sauce.”
“Oh, Pam. Yes, Yes. I have missed you so much. Please make me cum. I want to shoot my cum for you. Will you eat my cum. Please. I love the taste of my cum on your lips.”
“My sweet girl, your dick is hard in my hand. Your head looks amazing as my hand slides back and forth. Are you ready to cum for Pam?”
My legs tense up. The familiar feeling was traveling up through my legs. I knew I was at the edge of releasing my cum.
“Agghh. Agghh. Oh Pam. I am ccuummiinngg, honey. Look at me, shoot baby. Oh fuck, Agghh. It feels so good.”
“That is it, baby. Shoot your cum for Pam. It is hot and sticky. Keep cuming sweet girl. Look at the mess.”
Maria gave my dick one last squeeze to get my last drop. She placed her finger up to her lips to taste my cream. She knelt in front of me to lick the cum sliding down my legs. She stood up, and we embraced as she placed her lips to mine, and her tongue pushed my cum into my mouth.
Maria stepped back.
“Is this what you want Pam to do to you?”
I was looking at Maria as tears formed in my eyes.
“What is wrong, baby?”
“You sounded like Pam, and you made me feel special just like she does. You were tender.”
“My sweet girl, this is your special day, and I am sure that Pam would want you to enjoy being yourself. Now, I do not think this will get in your way.”
We took a shower using lavender-scented gel. After we finished, Maria took me to her make-up table. She was going to make my transformation into Kendra. On the table were eyeliner, lipstick, eye shadow, and mascara. I was getting excited.
“I am going to add blush to add color to your cheeks. I want Harry to be taken by surprise.”
“You have me looking entirely different. I feel like a woman. I hope that Harry likes it.”
“The true test will be to look at his crouch. When his dick starts to grow, you will know.”
We both laughed.
“That should do it.”
Looking in the mirror, it was not me. The person was beautiful with full red lips. I flashed a sexy smile. I was beginning to feel more like a woman. This was a new feeling for me.
“Now, it is time to see what surprise is in the box.”
The inside box was wrapped in pink paper with a bow. Here was a note, “To my sweet Kendra.” I placed the wrappings off to the side and removed the top. Inside was a satin, deep red dress; it felt soft to the touch.
“We need to get your lingerie on before we slip the dress on.”
Inside the box was a matching set of a red bra and thong. She included a pair of thigh-high stockings. Before placing those on, Maria had rubbed my body down with a jasmine-scented lotion. I took care of putting on the stockings so as not to get a run.
“My sweet girl, time to get your dress on.”
The dress slipped over my head, and it came midway down my thigh. It felt soft and smooth against my skin. It hugged my body in all the right places.
“Look at you. Yes. You look beautiful. Pam would be so proud of you.”
Looking in the mirror, I was stunned, and I was feeling sexy and horny.
“Look at you, so beautiful. Let me take a picture for Pam.”
“I hope I do not make Harry cum in his pants when he walks in the door.”
“He may not know how to handle himself. You will be the girl of his dreams.”
“These flat shoes will fit you.”
“I prefer the flats because I am not ready for any heels.”
As I walked around the room, the dress swayed with each step. My feminine side was coming to the surface. Maria had an unusual look on her face.
“Kendra, if I can be bold, if I were a guy, I would want to get in your panties and make love.”
“You know how to make a girl blush.”
We laughed.
“It is getting late, and Harry will be here shortly. We can see Harry when he pulls into the lot. You can go down the hall and wait five minutes. I will tell Harry that my friend Kendra will be dropping off a package and for him to open the door when she arrives.”
Twenty minutes later, Harry is pulling into the lot.
“You can go outside, down the hall, and wait.”
I made my way outside and watched Harry walk up to the door. I waited five minutes before knocking on the door.
Standing at the door, I rang the bell and heard footsteps. The handle turned, and the door opened.
Using a soft voice, “Hi. My name is Kendra, and I have a package for Maria.”
“Please come in, and I will let her know that you are here.”
As I walked in front of Harry, I thought about him looking at my ass. I made sure that I swayed slowly.
Harry showed me a chair in the living room. When I sat down and crossed my legs, my dress rose to show off my stocking-covered legs. Harry took a seat across from me. I wished that I could have read his thoughts. I could feel Harry’s eyes staring at me.
Maria came over to me in the room, and I stood up, and we kissed. We wanted to see what reaction we could get from Harry. We heard a soft moan.
“Maria, where are you hiding, Kevin? He was supposed to meet me here.”
“She is in the bedroom waiting.”
“Kendra, can you go and get Kevin?”
Harry did not recognize me. I made my way to the bedroom and waited a few minutes before returning. I came back and stood in front of Harry.
“What is going on here. I do not understand. Kendra, where is Kevin?”
Standing in front of Harry, I reached for his hands and placed them on my hips.
“Hi, Harry. I am now Kendra.”
The look on Harry’s face was priceless.
“Fuck. You look beautiful, and I did not recognize you. I could not take my eyes off your beautiful legs and shapely ass.”
“I am yours for the evening. I hope that you are horny because there is something special I have for you.”
Harry started rubbing his hands up and down my stocking-covered legs. He placed a hand over my cheeks and was rubbing my ass.
“To prove that you are excited to see me, I want you to get naked.”
Harry was off the chair and ripping his clothes off. His beautiful dick was sticking out with a drop of lubricant at the tip. Harry pulled me to kiss. Our tongues mingled.
“My. You are glad to see me, baby.”
I stepped back, reaching under my dress and pulling my panties down to free my dick.
“Baby, I want you to get on your knees and make love to my dick. You can suck all my sticky cum out.”
“Oh, Kendra. I’m still in awe of how beautiful you look. I want to feel your hard dick in my mouth.”
The next feeling was Harry’s mouth at the tip of my dick. Slowly, he pushed his head towards my stomach to engulf my shaft.
“Oh, baby, your mouth feels so good on my dick. Please suck me good and taste my sticky cum. Suck the head of my dick.”
Harry had a firm grip on my cheeks as his lips were sliding back and forth along my shaft as he was moaning.
“Yes, suck me, baby. Let me fuck your lips until I cum.”
My hips were moving in a slow circle. The tension was building up as my legs were shaking. In a manner of minutes, I was going to release a load of hot cum.
“Get ready baby. I am gonna cum hard in your mouth, suck me. Affgghh. Oh fuck. I am cuummiinngg. Eat my cum. Agghh. Yes, so good.”
Harry was moaning.
“Squirt your cum bay. Give me all your hot cum. You taste sweet. I love having you cum in my mouth.”
My cum was dripping out of the sides of his mouth while his head was going back and forth. I did not realize how much cum I was shooting. The feeling was intense.
Harry let my slippery dick pop out of his mouth, and he whispered, “Your dick tastes so good, sweetie.”
Maria was standing off to side watching us. She walked to Harry.
“Come here, Harry. I want to lick all the cum off your face. I love the taste of cum.”
Seeing the two kiss was sexy. I did not realize how much cum I had squirted. Maria’s tongue was moving across Harry’s lips and chin.
“Oh my. Kendra, your cum is sweet tasting.”
After we calmed down, Maria explained what was going to take place.
“Harry, I am going to videotape you and Kendra as you take her virginity.”
“This sounds wonderful. I have wanted this for so long. I am getting horny thinking about it.”
Harry looked at me.
“Kendra, I wanted to make love to you. Your tight love-hole is sexy, and I want to make you feel good.”
“I see that your dick is rock hard and dripping, but Kendra needs to freshen up her makeup and to clean up the mess you made between her legs. Give us a few minutes.”
We walked to the bathroom where Maria worked her magic. She was wearing an all-black set of lingerie: bra and panties, stockings, garter belt, and four-inch heels. She looked amazing.
“Alright, Kendra, you look delicious and ready to please. If you walked into a room, there would not be a soft dick in the place. My pussy feels wet looking at you. Are you ready?”
“I am more than ready. My tight love hole is ready to be penetrated. I have dreamed about this moment.”
We went back to the living room and Maria adjusted the camera. The red silk sheets were on the bed. Harry walked up to me and stared into eye. I could feel the head of his wet dick pressing against me.
The lights dimmed. I heard, “Ready.”
To be continued.