Debby the whore s office submission
- 4 years ago
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My Debby - Birthday Presents free porn video
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If you have not read my previous story a short setup. I had just helped Debby move into a house near her college campus. Debby, my girlfriend for 4 years, and I had our first experience of sexual intercourse a day ago. Her birthday is coming up very soon.
I called Debby the next day and asked how she was feeling. She said, “Thank you very much for asking. I am feeling fine, but I am a little sore. However I would not trade last night for anything.”
“I feel the same way,” I replied.
We spoke awhile longer about nothing in particular. I wasn't sure when I would see her or be with her again.
We didn’t speak again until a few days later, my birthday. She called me.
“Andy, I sorry I almost forgot about your birthday,” I could hear the sadness in her voice. “I don’t have anything for you.”
“It’s really all right. You were so busy getting ready for college and my classes start next week,” I responded.
We spoke about how her classes were going and how she was getting along with her housemates. Things sounded like they were going well. Debby was still excited and enthusiastic.
“I miss you Debby,” I said at the close of the call.
“I miss you too Andy. I love you!” Debby said with a serious tone that I hadn’t from her before.
“Debby, I love you too!” I said with all my heart.
We said our goodbyes. It pained me to get off the phone, but long distance was expensive in those days.
We spoke to each off and on over the next four weeks. I had made plans to go visit Debby on the weekend of her birthday. She said she had found a place for me to stay while I was there. She and her housemates had agreed on no men allowed overnight in the house, so I wondered what she had arranged.
The week before Debby called and asked if I could bring two of her friends with me for her birthday. I agreed.
The first was Sandy. Sandy, Debby, and I were in the same class in 1st and 2nd grade, since they grouped classes by neighborhood. Sandy was also in my class from 3rd to 6th grades in elementary school while Debby was in Chicago. Then Sandy and I went to the same junior high, where we had some classes together. Then of course Sandy, Debby, and I were in the same high school. Sandy was short, 5' 4”, petite. She had long brunette hair reaching down to the middle of her back. Her hair shimmered in the light. Sandy had light tan colored skin, her mother was part Native American. She was very cute and had a very melodic voice. Her smile would make one feel good inside.
The second was Peggy. She had the same school history as Sandy. Peggy was tall, about 5' 11”. She had reddish brown hair and was athletic. She had played on the girl's basketball team in high school and had gotten a partial scholarship to play in college. Peggy was not a ravishing beauty, but was still very pleasant to look at. We got along well because I also played basketball in high school.
Friday I drove over to Peggy’s house. I was told Peggy and Sandy would both be there. Sandy’s parents were very strict. They would have objected to Sandy “going off” with a guy that they had not met and approved of. Sandy had told them She was going to Debby’s with Peggy. Not a lie, but not the full truth. I put their bags in the back of the truck. We all got in the front seat with Sandy in the middle. We left on the 90 minute drive to Debby’s. Sandy said that Debby’s housemates were all gone this weekend. Sandy looked at Peggy and smiled, Peggy smiled back. We spoke about college on the way.
Sandy was going to a local community college and wanted to go into nursing. She was still living at home.
Peggy was going to the same college as I was. Unofficial captain’s practices had begun for basketball. We had taken the bus together to the college several times. Our schedules ended at different times so we didn’t go home together. She had not decided on a major yet, but was thinking about sport’s medicine.
I told them I was going to try to make the University basketball team as a walk on. I had been injured for about half of the season during my senior year. Colleges that had expressed interest had lost interest. I was going into veterinary medicine.
“We hear that you helped Debby move into the house off campus,” Peggy said stifling a giggle.
Sandy looked at Peggy with a look that made Peggy go silent. Then devilish grins appeared on their faces.
“Yes I did!” I said suspecting something was going on.
Soon we arrived at the house. Sandy and Peggy both were anxious to get into the house. I opened the door on the topper on the back of the truck and retrieved our bags. I followed them up to the door. Debby was waiting for us at the door. She had seen us drive up. I followed Sandy and Peggy up to the front door with their bags. I had left mine in the back of the truck.
Debby was telling them to go to the top of the stairs and that everything was set up there. They looked at Debby, then at me and snickered, before going up the stairs. I put the bags down and gave Debby a kiss and hug.
“I've missed you,” I said.
“I've missed you too,” Debby responded. “We experienced something so wonderful, then have been apart since.”
There was something in her voice that sounded weird to me. We walked up the stairs to the landing area where Debby had set up. There was a sofa, a couple of armchairs, and a low table with some food and drinks on it.
“What’s up?” I asked. “I can tell something more is going on than a birthday party.”
“This is going to be a sleepover. But not just for us girls, for you too. But you will not be getting much sleep,” Debby explained. Both Sandy and Peggy nodded in agreement. “However, there might be a slight problem,” she said before being interrupted by the doorbell.
Debby went downstairs to answer the door. I puzzled over what Debby had said.
“What is she talking about?” I asked Sandy and Peggy.
Peggy spoke first. “Debby had planned on just you and the 3 of us being here for a night of fun. But, Debby’s mom told Debby’s cousin about the party and she decided to come. She might ruin our plan,” Peggy said.
I was still not sure what she was trying to tell me. Maybe I was being a little slow. “Why would Debby’s cousin ruin the fun?” I asked. Both Sandy and Peggy giggled loudly.
“Debby has told us about your activities a few weeks ago. We want to have similar experiences,” said Sandy. I suddenly realized what was going on. “Debby’s cousin does not know anything about our plans. Debby hopes she can explain things to her cousin and Debby’s cousin will either agree to be quiet about it or agree to participate,” Sandy continued.
The door at the bottom of the stairs opened. “Go into the bedroom,” whispered Peggy.
I quickly moved to the bedroom, quietly closing the door behind me. I heard some discussion at the door downstairs. I heard Debby and then another voice, a male's voice. I went and sat on the bed. The door closed and I heard two sets of footsteps coming up the stairs. Then for several minutes there was a muffled discussion on the landing outside the door. When the discussion stopped the door opened. Debby motioned for me to come out.
“Andy this is Cindy, my cousin. Cindy this is Andy my boyfriend,” Debby introduced us. “The pizza also arrived.”
Cindy looked like she could have been Debby’s sister. She had the same shoulder-length sandy blonde hair and the same glistening blue eyes as Debby. Although Cindy was sitting she looked to be nearly as tall as Debby. Her breasts were big just slightly smaller than Debby’s. Cindy smiled a tentative smile as she looked me over.
“Let’s have the pizza while it is still hot,” said Debby. We all filled our plates and ate. I learned that Cindy was 18 in her first year of college in Madison. She had driven here after her late afternoon lab. Her mother and Debby’s mother were sisters. Throughout the meal Cindy kept nervously looking over at me. I smiled back at her. She would glance away, but would look over again in a short time.
After having ice cream and cake for dessert, Debby said, “Time for the first game. We are going cut cards. High card goes first.”
Debby drew a king, although I saw the deck was offset and that was where she cut. Knowing Debby this was part of her plan and neither Sandy nor Peggy seemed at all surprised. Sandy cut next and cut a 10. Peggy cut a 3, then Cindy cut an 8. It was confirmed later that it was setup for Debby to win.
I went to cut, however Debby stopped me. “You don’t need to cut silly. Come with me,” she said. She took my hand and led me to the bedroom. She shut the door behind us.
“I’ll set the timer for 30 minutes,” Peggy said from the other room.
Debby took off her clothes as she moved toward the bed. I removed my clothes as fast as I could. Debby jumped into my arms, wrapping her legs and arms around me. I grabbed her buns. Our lips met, pressing against each other. Our tongues quickly invaded each other’s mouths. My hands kneaded her buns. The nipples on her breasts hardened and poked into my chest. My penis began getting to stiffen and followed the crack up her rear end.
“I needed to be with you tonight,” she said. “It is your birthday present to me. The others, well think of it as my birthday present to you, since I forgot to even send you a birthday card.”
“Debby I don't know. Are you sure you are fine with this?” I asked.
“I planned it,” Debby said. “It is fine.”
I moved over to the bed and slowly laid her down on it. I kissed down her neck and onto her shoulder. I caressed the other side of her neck and shoulder with my hand.
“Mmmm,” Debby moaned.
I moved down her arms, then over to her breasts. I caressed one with my hand. I suckled the other one, Debby jerked, then sighed contentedly. Her nipple hardened in my mouth. I moved my lips over to the other breast. I swirled my tongue around her areola. Again she sighed and moaned. I kissed down her stomach, pausing at her bellybutton. I blew warm breath into it. She giggled.
After a minute or so of kissing around her bellybutton, I moved lower just before getting to her vaginal lips I realized Debby had shaved her pubic hair. Her lips were soft and smooth. Debby trembled and moaned her approval as I kissed and licked her slit.
“Turn around,” Debby commanded.
I turned around, putting my stiff penis just above Debby’s mouth. I kept my mouth on her pussy. Soon I felt her hand grab my penis and her tongue started licking the head. I had never felt pleasure like this. Each time she breathed out her warm breath caused my penis to grow and harden further. Then she enveloped the head of my penis with her mouth, still licking the head with her tongue.
I pushed my tongue into her slit, finding her clit I swirled my tongue around and across it several times. Debby starred breathing heavier and faster. She writhed around on the bed obviously enjoyed my mouth and tongue.
She took me deeper into her mouth. She began sucking and moving her head up and down stroking my penis with her lips and tongue. She choked a little when she tried to take me in deeper. My hard-on was now at it's full extent. I resisted cumming, not knowing if she wanted me to cum in her mouth.
I used my fingers to spread her pussy lips. I sucked on her clit making her squirm. I inserted a finger into her love hole. Debby let out a muffled scream of pleasure. I pushed my finger in and out of her. Going deeper each time. Her body tensed from head to toe. Her head and legs lifted up off the bed. I continued working her over with my tongue and fingers. Suddenly her head and legs fell back to the and she arched her back. Several times her pelvis pushed into my mouth then fell back to the bed. My penis still filled her mouth stifling ecstatic expressions of pleasure.
I was getting pushed to the edge of cumming. “Debby I am going to explode soon!” I exclaimed.
She recovered enough to say, “I want you inside me.”
I pulled out of her mouth, turned around, and attempted to insert myself into her love hole. I missed the first time sliding up toward her stomach across her clit. She jumped. The second time was more successful. I buried myself half the way. I paused there as someone knocked on the door.
“Ten minutes left,” Peggy said from the other side of the door.
The knock and interruption scared me slightly. Moving me away from climaxing. I slowly began moving inside Debby. Each stroke I moved deeper into her.
Once completely inside her she gasped, “You feel so wonderful inside me. Please make me orgasm again!”
I quickened my pace. I felt my balls tighten. I was on the edge when her pussy walls clamped around me. I exploded inside her. I shot stream after stream as she squirmed and arched her back. She moaned trying to muffle her exclamations of pleasure not wishing the others to hear.
Again there was a knock on the door. “two minutes,” Peggy said.
The bedroom had an entrance to the bathroom. There was one from each bedroom upstairs and one from the landing area. I stood, went into the bathroom and started to clean up. Debby joined me. She cleaned up, went back to the bedroom, put on her top and pants, leaving her underwear on the floor. After I finished I turned to go back to the bedroom. The door to the main room opened and Cindy was standing there. She was startled. I was standing there naked. She looked at my face, then her eyes moved down to my crotch. Her eyes grew big when she saw my mostly limp penis. She just stared for several seconds. Her face turned bright red, before backing out of the door.
“Sorry!” Cindy said as she closed the door.
I heard Sandy and Peggy giggling on the other side of the door. I went back into the bedroom and put on my shirt and underwear.
The third knock was followed by Peggy saying, “Time’s up.”
The door opened. Peggy and Sandy were standing there. Both were still giggling and had mischievous smiles on their faces. Sandy stepped in, Debby walked out, Peggy closed the door.
“30 minutes,” Peggy said.
Sandy stood by the door.
“Just so you know, this was Debby’s idea. She told us about you and her having sex. She told Peggy and I about how gentle and caring you were with her. She wanted you for her birthday,” she explained. “Debby said she is okay with whatever happens between us. She wanted you to be our first time.”
“Thanks for explaining things to me,” I said.
I was surprised Sandy was here. Sandy’s parents were very strict. I knew that her parents didn't let their daughter’s date until 16. Then only in groups or chaperoned situations until they were 18. They didn't even allow boys into the house unless they invited them.
Sandy was very pretty. Her dark brown eyes and long dark hair, plus her light tan skin color made her look exotic. Her voice was a joy to listen to. When she smiled at you your heart melted. She was slim and petite. She had small perky breasts that were perfectly proportioned for her body. I could tell she was nervous. She stood by the door not moving or speaking.
“Sandy, it is up to you as to what happens during the next 30 minutes. I am not going to pressure you into anything. I will ask you before I do anything. You can say “no” or “stop” at anytime,” I assured her. I watched her face and body relax. Then she gave me that wonderful smile. The tension left the room.
“Thanks! Debby said that you were kind, gentle, and understanding.”
“What do you want to do first?” I asked.
“Let’s take off our clothes,.” Sandy said. I removed my shirt. “Wait I want you to take off my clothes, then I will take off the rest of yours.”
Sandy walked over to me and gave me a hug. I hugged back. My penis started to come to life pressing against my underwear and against Sandy’s stomach because of the difference in our heights. I untied the string holding up her blouse and it dropped to the floor. I hooked my thumbs under the waistband of her pants and pulled them down. She stepped out of them. I touched her shoulders, she jumped a little. Her skin was soft and silky smooth.
“Do you want me to continue?” I asked. She nodded. I reached around and unhooked her bra. I slipped the straps off her shoulders. Slowly her breasts were exposed. They were exquisite, they were not large, but were so round and perfect. I leaned over and we kissed. My hand came around to the front. I cupped her left breast with my right hand. She trembled at my touch. I started to pull my hand away, but Sandy grabbed it and pushed it back in place. I massaged her breast, then used my other hand on her other breast.
Sandy tilted her head backward. “That feels so good. Don't stop,” Sandy cooed.
My penis came to full attention. Creating a tent in my underwear. Sandy noticed and pulled my underwear down. They dropped to the floor. My penis popped out, pointing toward the ceiling. She starred for quite some time.
“May, may I touch it?” she queried.
“Yes, go right ahead,” I answered.
She slowly put her fingers on the head of my penis. She traced the curve of my member. From tip to base. It jumped, she giggled. She wrapped her fingers around my shaft and began stroking up and down it’s length. I continued massaging her breasts. I felt the blood pulsing against her fingers. I also realized the 30 minutes was disappearing rapidly.
I pulled her panties down and they fell to her ankles. With the same hand I reached down trying to find the place between her legs. Because of the difference in our height, my arm was not long enough. Realizing the problem Sandy gently pushed me back until I had to sit on the bed. I could now easily reach her pussy. She could still stroke me.
I traced the crack along her pussy lips. They were very warm and wetness was seeping between her lips. I noticed Sandy had also shaved her pubic hair as Debby had done. I pushed one finger between her lips. She was definitely wet. My finger slid easily the full length of slit. She cooed and moaned. I found her love button on the upstroke. She jumped “oooooo” coming out of her mouth. I circled her clit then ran my finger over it. She nearly collapsed to the floor.
Looking down at my penis Sandy said, “Do you think that will fit inside me? It is so big.”
“The only way to find out is to try,” I replied.
She pushed me down on the bed. I lay down on the bed with my penis sticking up in the air. Sandy crawled up on the bed and straddled me. I held her pussy lips apart as she lowered herself and guided me into her.
The head of my penis pushed against her. She pushed down several times. I continued to massage her breasts. Her nipples were now hard. I rolled them between my fingers. She pressed them into my hands. My penis had encountered a barrier. She pushed harder and nothing happened.
“My hymen,” Sandy said quietly.
“Take things as slow as you need to,” I said. “This is probably going to hurt some.”
“I know. My sister warned me,” she said.
I had to wonder what discussion she had had with her sister where this subject would have come up. I knew her oldest sister was married. Sandy pushed down. I could see the pain on her face. She pushed a little harder. I could feel it starting to give way. With one last push from her I slid farther into her. Sandy bit her lip and tears were in her eyes. It was good she was already wet.
“Hold still until the pain goes away,” I suggested. “We can stop completely if you wish.”
“It hurts and feels good at the same time,” she said. “Let’s give it a little time. It feels weird to have something so big inside me. I feel it pulsing inside me. The pain is slowly diminishing.”
A minute or so passed before she started moving again. Up and down slowly taking me more into her tight hole. I moved one hand to her clit and teasing it with my fingertips.
“Ahhh, keep that up. It helps the pain,” she instructed.
Soon I was completely inside her.
“Wow! You’re all inside me,” she said. “I can’t believe it. I feel so stuffed.”
She paused for several seconds then started slow long moves up then back down. I was in heaven. Sandy was so tight the sensation was incredible. Sandy increased the pace. I started moving in coordination with her. Her breathing came faster and shorter. I increased my pressure on her love button. Her head went back and she emitted sounds of great pleasure. I could feel my balls tighten.
“I am about to cum,” I warned her.
She said nothing, but increased the pace.
“5 minutes,” Peggy said from the other side of the door.
We paid no attention. I was not going to last much longer. I held off as best I could. The walls of her vagina clamped around me. I exploded into her. She came. Her orgasm shook her body. Her muscles spasmed around me. Sandy was barely able to contain her screams.
After several seconds she collapsed on top of me. I gave her a hug squeezing her body to mine. She was so warm. She was still breathing heavily. I kissed the top of her head. She lifted her head, inched up and we kissed. Her lips were soft, full, and smooth. We got up and quickly cleaned up. Sandy put on her top and pants. I put on my shirt and underwear.
“Time’s up,” came from the door as it opened.
Peggy, Debby, and Cindy were all standing there. Debby and Cindy stepped into the room. Sandy walked out smiling. Peggy closed the door.
“Cindy is very nervous about this,” Debby said.
“Cindy, it is your choice as to what happens. You can leave the room now if you wish,” I assured Cindy. “We will only do what you want. I will wait for your agreement at each step. You can say ‘stop' at any time.”
Cindy looked at me and then Debby.
“It’s your choice,” Debby said. “You can trust him to do what he says.”
We waited for Cindy to say something. Finally she said, “Can you put your pants on.”
I had forgotten that I was standing there in my underwear. “Sure!”, I said looking around for my pants.
They were in a pile in front of the bed with Debby and Sandy’s under wear. I picked them up and put them on.
“You can leave Deb,” Cindy said, still with a slight quiver in her voice.
Debby left. “We are giving you 40 minutes,” she said as the door closed.
I heard Peggy objecting to the additional time on the other side of the door.
“Please sit down on the bed,” Cindy said softly. I complied, leaving her plenty of room to chose how close to me she would sit if she decided to sit. She came and sat on the bed about 3 feet away from me.
“I was not expecting anything like this. I was just coming over for a birthday sleepover,” she said. “When Debby told me what she had planned, I was surprised, scared, and nervous. I have never done anything sexual, except alone by myself.”
“You don't know anything about me. Would it be alright if I told you about myself?” I asked.
“Deb just told me you were a nice guy and she likes you a lot,” she responded. “Go ahead tell me about yourself.”
“My name is Andy,” I started. “I am the oldest of 4 kids, 2 sisters and one brother. I live a block over and a block south from Debby’s. Debby and I were in the 1st and 2nd grade together, then she moved away. Peggy, Sandy, and I were in the same elementary school class through the 6th grade. We were also in the same Junior High. When Debby came back we were all in the same High School,” I told her.
Cindy then told me a little about herself. “I am Debby’s cousin. Her mother and my mother are sisters. I am an only child, like Deb. My parents got divorced about five years ago. I live over in the next city. Deb and I have been very close. I am about 9 months younger than her. I visited her in Chicago several times. I look up to Deb and trust her judgement,” she explained.
I took a good look at Cindy. She was really a slightly younger version of Debby. Same dishwater blonde hair. Same deep blue eyes. She was just an inch or 2 shorter than Debby. Her chest was just slightly smaller. She finally started to smile and relaxed a little.
“May I sit closer to you?” Cindy asked.
I nodded yes. She moved over next to me.
“Please put your arm around me,” she requested.
I put my arm around her. I flashed back to the times I had my arm around Debby.
“I'm sorry I walked in on you in the bathroom,” she said. “Sorry I starred. I had never seen a penis before, except in pictures.”
“That's okay. I understand,” I said.
She was quiet for some time. I sensed that she was trying to get the courage to say something. She fidgeted.
“Ah, do … do you think I could see your penis again?” she stammered.
I stood and took off my pants and then my underwear. I sat back down next to her. I spread my legs to give her a good view. She starred at it for quite some time.
“May … may I touch it?” she asked.
“Sure, go ahead,” I replied.
Hesitantly her hand moved toward it. She acted like it was dangerous. Her fingertips touched it and then pulled away. Then touched it again. She pushed lightly.
“It is soft and kind of spongy. How does it get hard?” she asked.
“It will get hard if it gets stimulated by contact or I see something that arouses me,” I told her.
She continued to rub my penis with her fingertips. I could feel the blood flow starting to concentrate there.
“Mmmm,” I said to encourage her.
“Does … does that feel good?” she asked.
“Yes it does,” I answered.
My penis began to get larger, but was still quite soft.
“May I wrap my fingers around it?” Cindy asked.
“Sure,” I answered.
She grasped it and started calmly pumping up and down it’s length. It began to swell. Her face showed some amazement. I sat still and enjoyed the pleasurable feeling.
“That really feels great,” I told her.
“What would you have to see to get aroused?”
“I do not want to push you to do anything You do not want to do,” I said. “But the first step would be to take your top off.”
Her hand paused as she considered my answer.
“Ok, but just looking, no touching,” she said removing her t-shirt.
I watched as her bra became visible. She had obviously done some tanning over the summer. There was a tan line just above her bra. Above the line her skin was a moderate tan. Below the line her skin was milky white. I smiled as I looked at her breasts. She nervously smiled back.
They were good sized, maybe a large C or a small D. Her bra was a little small. Her breasts pushed against the material.
“Do you like them?” she asked.
“Yes I do!” I answered. “Just look at my penis and then feel my penis.”
She looked down and then squeezed my penis. It had become longer and harder.
She smiled a bigger smile and said, “Did I do that?” I nodded yes. “Should I take my bra off?”
“Only if you want to,” I replied.
Again she gave it some thought. She reached back to unhook her bra. She was nervous and seemed to be having difficulty.
“Do you want me to help?” I asked.
She turned her back to me. I quickly unhooked her bra. I could now see the lines of the bikini top she must have worn while tanning. I slipped the bra straps off her shoulders. My fingers caressed her shoulders as I did so. She shivered. She held her bra in place with her arm.
“May I caress your back?” I became more bold.
“Yes,” she said without hesitation.
I ran my fingers back across her shoulders then up the sides of her neck. I massaged both sides just under her ears.
“Ohhh … that feels good,” she said. I continued for several seconds, before my fingers traveled down her back on each side of her spine. Again she shivered. I wanted to go lower, but decided against it. I went back up to her neck massaged each side at the base of her neck. Again she shivered, her skin had goosebumps.
“Are you cold?” I asked.
“No I just feel a little tingly,” came her response.
She moved her arm letting her bra fall to the floor. My fingers traveled down her back again. She reached back and found my penis. She went back to a slow, gentle stoke with her hand encircled around it. I stroked my fingers up both sides of her body, then across her collar bone to the middle of her back.
“Does it still get harder and bigger?” she questioned. Not waiting for an answer she asked, “Would it help if you massaged my breasts with your hands?”
“Yes, it would!” I responded. “Do you want me to do that?”
“Yes, if what I am doing to you feels good, I am sure that would feel good to me. Please be gentle, they can be very sensitive,” she requested.
“I will!” I assured her.
I moved my fingers across her shoulders and down her arms. I paused then moved to cup the underside of her breasts. Cindy drew in a deep breath. I moved closer to her. The tip of my penis touched her lower back. I leaned forward and kissed her shoulder. She shuddered. My hands moved upward to cover her nipples. They were hard and pressed into the palms of my hands. She took in another deep breath.
“Yes, yes keep going. It feels very good,” Cindy said.
I rubbed her areolas in circles around the nipples. “Oooos” and “ahhhhs” came from her lips. Her head tipped back in pleasure. Her eyes were closed and there was a smile on her face. I thought about dropping a hand down into her panties. I decided against it until she suggested it. Meanwhile my penis tapped against her lower back each time she stroked it. I was nearly at full length and hardness, but because I had already come twice I was not close to cumming again. I moved a little closer to her making my penis tap farther up her back.
Then Cindy said, “I have never felt like this. It feels so hot between my legs. Ah, my panties are getting wet.”
She abruptly stood. She pulled down her pants and panties. Since she was still facing away from me her rear end was in front of me at eye level. I reached out and touched her butt cheeks. She backed up slightly, so I grabbed them with my hands. I squeezed them both together then alternately. She pushed back harder, I went lower until I was rubbing between her legs. She opened her legs so I slipped one hand between them and reaching up to her pussy. I started at the bottom and moved along the outside slowly up to the top, then back to the bottom. I was surprised at the amount of pubic hair she had. I pulled a hair a couple of times. She twitched each time. Cindy was very wet. I could definitely smell her sweet, musky odor. I moved a couple of fingers up the crack between her lips. She moaned a low deep moan. She wobbled slightly. I moved my finger back down to the bottom of her pussy lips. I pressed my fingers between her lips and they immediately became wet. I moved to the top of her lips again. She jerked as I rubbed across her clitoris for the first time.
“Wow! Stay there,” she requested.
I circled around her clit several times with my fingers. She shuddered and trembled. I rubbed over her clitoris. Her legs gave way and she sat on my lap. My hand was trapped.
“Wow, I never felt anything like that,” she said.
My penis was “trapped” between us. She sat there for a minute or two. A knock came at the door.
“10 minutes,” came Peggy’s voice.
Cindy stood up almost immediately. She turned around. I got my first look at her gorgeous body and breasts. Her breasts looked larger than I had originally thought. She smiled at me. It was the same smile I had seen on Debby’s face a number of times. I smiled back.
“Not much time left! I am going for it,” she said as she took ahold of my penis.
She came closer and guided me toward her love hole. My penis touched her vaginal lips. With a slight adjustment I started to enter her. She paused. Obvious satisfaction took over her face. I wrapped my arms around her, encouraging her to go farther. She pushed down I encountered a obstacle. She winced.
“It’s going to hurt, at least for awhile,” I warned.
I could tell she was getting her courage up, readying herself for the anticipated pain. Her eyes and mouth closed. She pushed and almost like a pop her hymen gave way. I slid into her. She again was sitting on my lap, but this time facing me.
“Ouch, that hurt! I am going to get up,” she said. She started to stand up, but stopped. “That hurts too!”
“Just sit still. I am sure the pain will subside,” I suggested.
I stroked her hair, then her cheek. I put my hand behind her head, then I kissed her. I pulled back, but she moved forward giving me a seductive kiss. My penis jerked inside her.
“That felt good,” she said. “You are so big.”
She slowly started moving up and down. She was tight, but extremely slick. She began moving faster. I moved in sync with her. I grabbed her butt cheeks. Cindy began breathing fast and shallow. I could feel myself quickly reaching the point of no return.
“I’m going to cum soon,” I warned her.
She continued without interruption. I could feel her vaginal walls tighten around me. She breathed in deeply then held her breath. Her orgasm took over her body. She shuddered and jerked. She spasmed around my penis. I exploded inside her, ejaculating 3 streams into her.
She fell into me. Laying on top of me on the bed. Cindy panted, then slowly returned to normal. I hugged her enjoying the feeling of her soft skin pressed against my body. The inevitable knock came at the door.
“Two minutes,” Peggy said.
Cindy rolled off, stood up and walked into the bathroom. I heard the water come on. I stood and joined her. She turned, put her arms around me, and kissed me.
“Thank you! I never knew I could feel that way. Thank you!” she said.
She walked back into the bedroom. I cleaned up. I finished putting on my shirt and underwear just as Peggy opened the door. Peggy stepped in, Cindy walked out, Debby closed the door.
“30 minutes Peggy,” Debby said with amusement in her voice.
Peggy stood still for a few seconds.
“What are you waiting for?” she asked. “Get your clothes off!”
She removed her shirt and pants. I removed my shirt and underwear. She stood with her bra and underwear in place. Peggy was tall about 5' 11”. She had an athlete’s body, firm and tight. She was thin and muscled but not overly so. She had nice symmetrical B-cup breasts. Her legs were long and well toned.
Peggy had always been more aggressive than most of the other girls. She liked sports and joined in with the boys when we played games. Some would have called her a tomboy, but that would have been incorrect. She was very feminine. She was very pretty, not beauty contestant beautiful, but very attractive.
She stepped over to me. “What are you waiting for,” she asked. Take my underwear off!”
It was obvious she was not wasting any time. I reached around her and unhooked her bra and let it fall. I leaned over taking one of her nipples into my mouth. I used my thumbs to drop her panties to the floor. Her nipples were larger than those of any of the other three girls. I gently sucked and licked one nipple while I teased the other with my fingers. She pushed my head tighter to her breast. I sucked harder and give a slight pinch to the other. Before long she took my head into both her hands, pushing it up until our lips met. I hugged her close while our tongues explored each other’s mouths.
Her breasts were pushed up against my chest. Her nipples were hard and erect. My penis started to come to attention. It pushed up against her crotch. She spread her legs. My penis pushed up between them, rested along the crack of her vaginal lips. She closed her legs slightly “trapping” my penis. I could feel a warm liquid on the top side of my rod. It continued to grow and stiffen.
“Mmmm,” Peggy moaned. “Somebody is getting excited.”
She began moving her hips away and then back toward me. Very slowly and a short distance at first. More of the warm liquid covered my penis from the top then moving down the sides. I started moving in coordination with her, being careful not to slip out from between her legs. Peggy continued to moan and quicken her pace. My penis was well coated with her juice. It moved between her pussy lips.
It was a good thing I had already cum a few times earlier or I may have exploded right then. Then on one stroke the head on my penis rubbed up on her clitoris.
“Ooooo,” said Peggy as she jumped. “That sure felt good.”
She took my penis in her hand, rubbing it against her clitoris. She varied the motion and the pressure of the head on her love button. She shook and shuddered. After some time she jerked. My penis slipped into her love hole. Peggy paused. I paused. She pushed forward I went deeper into her. I had expected to encounter her hymen. I waited to start thrusting.
“What are you waiting for?” Peggy asked. “Don't you like this?”
“I don't want to hurt you,” I replied. “It can hurt the first time.”
“Are you worried about my hymen? I lost it about a year ago with the handle of a brush. It hurt for a day or so,” she explained.
Again she started moving her hips away and toward me. Peggy was tight. I pushed into her. She pushed back. Soon I was fully into her. Her vaginal muscles squeezed and relaxed on me. Then they rolled from the head toward the base of my penis. This was different than the feeling when the others had orgasms. This was controlled and deliberate.
“I've been practicing on my hairbrush,” she said. “You are so much bigger than the handle of my brush. It feels so amazing.”
Her eyes remained shut as she concentrated on what she was doing. I started moving out, then back in. She tightened as I pulled out and relaxed as I pushed in. I quickened the pace. Peggy grunted and moaned. I felt my testicles spasm releasing my seed into her. This triggered her orgasm. She trembled shaking from head to toe. It felt as if she was squeezing every last drop out of me. We held each other up.
We then went to the bathroom to clean up. Peggy wet a small towel, Turned around and began cleaning me. Soft, sensual, thorough attention started bringing my penis to life again. She handed the towel to me. I cleaned her with careful attention to her clitoris and love hole. My fingers strayed a few times to Peggy’s delight.
She took my hand led me back into the bedroom. She laid down on the bed. I laid down beside her, face to face.
“I don’t know how much time is left. Why don’t you put your head the other way,” she requested.
I flipped around so my face was in front of her pussy. She was looking straight at my slightly erect penis. The inevitable knock came at the door.
“10 minutes,” said Debby.
I felt Peggy’s fingertips on the head of my penis. They moved lightly around it’s circumference, then across the tip. It jumped, to Peggy’s delight. She continued moving her finger down the top to the base.
“Your hair is very coarse and wiry,” she said more to herself than anything.
I had reached forward and was using my fingertips on her pussy. I noticed she had shaved her pubic hair. I learned later that Debby, Sandy, and Peggy had decided together to shave themselves. I caressed down the outside of her lips then back to the top. Peggy squirmed. I moved down the crack between her lips then back up repeating this several times. I could feel the heat coming from inside her. I could smell a musky odor as liquid appeared from the crack. I pushed a finger into her, continuing to move it up and down. It slid easily with her lubricant. She pushed against my finger inviting me in deeper.
Her fingers continued exploring my rod. Rubbing up both sides, then down the underside. This felt amazing. I stiffened, bouncing with each heartbeat. Peggy moved down to my testicles exploring and caressing each one in turn. She gently scratched the underside sending me into ecstasy.
I was determined to return the favor. I pushed my finger deeper into her. I found her love button, I teased it with increasing pressure. Peggy jumped and bucked pushing her pelvis into my finger. I used two fingers to spread her pussy lips. Her pink clit was clearly visible. I put my head closer and tickled it with my tongue. She reacted immediately, pushing up against my tongue. She moaned in approval.
She shifted. I felt her warm breath on the tip of my penis, just before feeling her lips kissed the head. Soon her mouth encircled it. The warmth was entrancing. Her tongue licked the tip causing me to go to full size. She began taking me in deeper.
Her breath came in short puffs. Her muscles stiffened. Her legs squeezed together, causing my head to be forced back from her pussy. Peggy shook and spasmed reaching her climax. At the peak again the knock came at the door.
“Time is almost up,” came Sandy’s voice.
“Give us a second to clean up,” I replied knowing Peggy was unable to.
“Ok,” came a trio of voices, followed by giggles.
I stepped into the bathroom, cleaned up, then back to the bedroom as Peggy entered. I dressed completely. I went out to the main room. Debby, Sandy, and Cindy were all naked. Peggy stepped out still naked.
“Who do you think you are?” Debby asked. “Why do you have your clothes on?”
They surrounded me pulling and tugging until my clothes were all on the floor. I wondered was going to happen next.
(To be continued) -->
If you have not read my previous story a short setup. I had just helped Debby move into a house near her college campus. Debby, my girlfriend for 4 years, and I had our first experience of sexual intercourse a day ago. Her birthday is coming up very soon.
I called Debby the next day and asked how she was feeling. She said, “Thank you very much for asking. I am feeling fine, but I am a little sore. However I would not trade last night for anything.”
“I feel the same way,” I replied.
We spoke awhile longer about nothing in particular. I wasn't sure when I would see her or be with her again.
We didn’t speak again until a few days later, my birthday. She called me.
“Andy, I sorry I almost forgot about your birthday,” I could hear the sadness in her voice. “I don’t have anything for you.”
“It’s really all right. You were so busy getting ready for college and my classes start next week,” I responded.
We spoke about how her classes were going and how she was getting along with her housemates. Things sounded like they were going well. Debby was still excited and enthusiastic.
“I miss you Debby,” I said at the close of the call.
“I miss you too Andy. I love you!” Debby said with a serious tone that I hadn’t from her before.
“Debby, I love you too!” I said with all my heart.
We said our goodbyes. It pained me to get off the phone, but long distance was expensive in those days.
We spoke to each off and on over the next four weeks. I had made plans to go visit Debby on the weekend of her birthday. She said she had found a place for me to stay while I was there. She and her housemates had agreed on no men allowed overnight in the house, so I wondered what she had arranged.
The week before Debby called and asked if I could bring two of her friends with me for her birthday. I agreed.
The first was Sandy. Sandy, Debby, and I were in the same class in 1st and 2nd grade, since they grouped classes by neighborhood. Sandy was also in my class from 3rd to 6th grades in elementary school while Debby was in Chicago. Then Sandy and I went to the same junior high, where we had some classes together. Then of course Sandy, Debby, and I were in the same high school. Sandy was short, 5' 4”, petite. She had long brunette hair reaching down to the middle of her back. Her hair shimmered in the light. Sandy had light tan colored skin, her mother was part Native American. She was very cute and had a very melodic voice. Her smile would make one feel good inside.
The second was Peggy. She had the same school history as Sandy. Peggy was tall, about 5' 11”. She had reddish brown hair and was athletic. She had played on the girl's basketball team in high school and had gotten a partial scholarship to play in college. Peggy was not a ravishing beauty, but was still very pleasant to look at. We got along well because I also played basketball in high school.
Friday I drove over to Peggy’s house. I was told Peggy and Sandy would both be there. Sandy’s parents were very strict. They would have objected to Sandy “going off” with a guy that they had not met and approved of. Sandy had told them She was going to Debby’s with Peggy. Not a lie, but not the full truth. I put their bags in the back of the truck. We all got in the front seat with Sandy in the middle. We left on the 90 minute drive to Debby’s. Sandy said that Debby’s housemates were all gone this weekend. Sandy looked at Peggy and smiled, Peggy smiled back. We spoke about college on the way.
Sandy was going to a local community college and wanted to go into nursing. She was still living at home.
Peggy was going to the same college as I was. Unofficial captain’s practices had begun for basketball. We had taken the bus together to the college several times. Our schedules ended at different times so we didn’t go home together. She had not decided on a major yet, but was thinking about sport’s medicine.
I told them I was going to try to make the University basketball team as a walk on. I had been injured for about half of the season during my senior year. Colleges that had expressed interest had lost interest. I was going into veterinary medicine.
“We hear that you helped Debby move into the house off campus,” Peggy said stifling a giggle.
Sandy looked at Peggy with a look that made Peggy go silent. Then devilish grins appeared on their faces.
“Yes I did!” I said suspecting something was going on.
Soon we arrived at the house. Sandy and Peggy both were anxious to get into the house. I opened the door on the topper on the back of the truck and retrieved our bags. I followed them up to the door. Debby was waiting for us at the door. She had seen us drive up. I followed Sandy and Peggy up to the front door with their bags. I had left mine in the back of the truck.
Debby was telling them to go to the top of the stairs and that everything was set up there. They looked at Debby, then at me and snickered, before going up the stairs. I put the bags down and gave Debby a kiss and hug.
“I've missed you,” I said.
“I've missed you too,” Debby responded. “We experienced something so wonderful, then have been apart since.”
There was something in her voice that sounded weird to me. We walked up the stairs to the landing area where Debby had set up. There was a sofa, a couple of armchairs, and a low table with some food and drinks on it.
“What’s up?” I asked. “I can tell something more is going on than a birthday party.”
“This is going to be a sleepover. But not just for us girls, for you too. But you will not be getting much sleep,” Debby explained. Both Sandy and Peggy nodded in agreement. “However, there might be a slight problem,” she said before being interrupted by the doorbell.
Debby went downstairs to answer the door. I puzzled over what Debby had said.
“What is she talking about?” I asked Sandy and Peggy.
Peggy spoke first. “Debby had planned on just you and the 3 of us being here for a night of fun. But, Debby’s mom told Debby’s cousin about the party and she decided to come. She might ruin our plan,” Peggy said.
I was still not sure what she was trying to tell me. Maybe I was being a little slow. “Why would Debby’s cousin ruin the fun?” I asked. Both Sandy and Peggy giggled loudly.
“Debby has told us about your activities a few weeks ago. We want to have similar experiences,” said Sandy. I suddenly realized what was going on. “Debby’s cousin does not know anything about our plans. Debby hopes she can explain things to her cousin and Debby’s cousin will either agree to be quiet about it or agree to participate,” Sandy continued.
The door at the bottom of the stairs opened. “Go into the bedroom,” whispered Peggy.
I quickly moved to the bedroom, quietly closing the door behind me. I heard some discussion at the door downstairs. I heard Debby and then another voice, a male's voice. I went and sat on the bed. The door closed and I heard two sets of footsteps coming up the stairs. Then for several minutes there was a muffled discussion on the landing outside the door. When the discussion stopped the door opened. Debby motioned for me to come out.
“Andy this is Cindy, my cousin. Cindy this is Andy my boyfriend,” Debby introduced us. “The pizza also arrived.”
Cindy looked like she could have been Debby’s sister. She had the same shoulder-length sandy blonde hair and the same glistening blue eyes as Debby. Although Cindy was sitting she looked to be nearly as tall as Debby. Her breasts were big just slightly smaller than Debby’s. Cindy smiled a tentative smile as she looked me over.
“Let’s have the pizza while it is still hot,” said Debby. We all filled our plates and ate. I learned that Cindy was 18 in her first year of college in Madison. She had driven here after her late afternoon lab. Her mother and Debby’s mother were sisters. Throughout the meal Cindy kept nervously looking over at me. I smiled back at her. She would glance away, but would look over again in a short time.
After having ice cream and cake for dessert, Debby said, “Time for the first game. We are going cut cards. High card goes first.”
Debby drew a king, although I saw the deck was offset and that was where she cut. Knowing Debby this was part of her plan and neither Sandy nor Peggy seemed at all surprised. Sandy cut next and cut a 10. Peggy cut a 3, then Cindy cut an 8. It was confirmed later that it was setup for Debby to win.
I went to cut, however Debby stopped me. “You don’t need to cut silly. Come with me,” she said. She took my hand and led me to the bedroom. She shut the door behind us.
“I’ll set the timer for 30 minutes,” Peggy said from the other room.
Debby took off her clothes as she moved toward the bed. I removed my clothes as fast as I could. Debby jumped into my arms, wrapping her legs and arms around me. I grabbed her buns. Our lips met, pressing against each other. Our tongues quickly invaded each other’s mouths. My hands kneaded her buns. The nipples on her breasts hardened and poked into my chest. My penis began getting to stiffen and followed the crack up her rear end.
“I needed to be with you tonight,” she said. “It is your birthday present to me. The others, well think of it as my birthday present to you, since I forgot to even send you a birthday card.”
“Debby I don't know. Are you sure you are fine with this?” I asked.
“I planned it,” Debby said. “It is fine.”
I moved over to the bed and slowly laid her down on it. I kissed down her neck and onto her shoulder. I caressed the other side of her neck and shoulder with my hand.
“Mmmm,” Debby moaned.
I moved down her arms, then over to her breasts. I caressed one with my hand. I suckled the other one, Debby jerked, then sighed contentedly. Her nipple hardened in my mouth. I moved my lips over to the other breast. I swirled my tongue around her areola. Again she sighed and moaned. I kissed down her stomach, pausing at her bellybutton. I blew warm breath into it. She giggled.
After a minute or so of kissing around her bellybutton, I moved lower just before getting to her vaginal lips I realized Debby had shaved her pubic hair. Her lips were soft and smooth. Debby trembled and moaned her approval as I kissed and licked her slit.
“Turn around,” Debby commanded.
I turned around, putting my stiff penis just above Debby’s mouth. I kept my mouth on her pussy. Soon I felt her hand grab my penis and her tongue started licking the head. I had never felt pleasure like this. Each time she breathed out her warm breath caused my penis to grow and harden further. Then she enveloped the head of my penis with her mouth, still licking the head with her tongue.
I pushed my tongue into her slit, finding her clit I swirled my tongue around and across it several times. Debby starred breathing heavier and faster. She writhed around on the bed obviously enjoyed my mouth and tongue.
She took me deeper into her mouth. She began sucking and moving her head up and down stroking my penis with her lips and tongue. She choked a little when she tried to take me in deeper. My hard-on was now at it's full extent. I resisted cumming, not knowing if she wanted me to cum in her mouth.
I used my fingers to spread her pussy lips. I sucked on her clit making her squirm. I inserted a finger into her love hole. Debby let out a muffled scream of pleasure. I pushed my finger in and out of her. Going deeper each time. Her body tensed from head to toe. Her head and legs lifted up off the bed. I continued working her over with my tongue and fingers. Suddenly her head and legs fell back to the and she arched her back. Several times her pelvis pushed into my mouth then fell back to the bed. My penis still filled her mouth stifling ecstatic expressions of pleasure.
I was getting pushed to the edge of cumming. “Debby I am going to explode soon!” I exclaimed.
She recovered enough to say, “I want you inside me.”
I pulled out of her mouth, turned around, and attempted to insert myself into her love hole. I missed the first time sliding up toward her stomach across her clit. She jumped. The second time was more successful. I buried myself half the way. I paused there as someone knocked on the door.
“Ten minutes left,” Peggy said from the other side of the door.
The knock and interruption scared me slightly. Moving me away from climaxing. I slowly began moving inside Debby. Each stroke I moved deeper into her.
Once completely inside her she gasped, “You feel so wonderful inside me. Please make me orgasm again!”
I quickened my pace. I felt my balls tighten. I was on the edge when her pussy walls clamped around me. I exploded inside her. I shot stream after stream as she squirmed and arched her back. She moaned trying to muffle her exclamations of pleasure not wishing the others to hear.
Again there was a knock on the door. “two minutes,” Peggy said.
The bedroom had an entrance to the bathroom. There was one from each bedroom upstairs and one from the landing area. I stood, went into the bathroom and started to clean up. Debby joined me. She cleaned up, went back to the bedroom, put on her top and pants, leaving her underwear on the floor. After I finished I turned to go back to the bedroom. The door to the main room opened and Cindy was standing there. She was startled. I was standing there naked. She looked at my face, then her eyes moved down to my crotch. Her eyes grew big when she saw my mostly limp penis. She just stared for several seconds. Her face turned bright red, before backing out of the door.
“Sorry!” Cindy said as she closed the door.
I heard Sandy and Peggy giggling on the other side of the door. I went back into the bedroom and put on my shirt and underwear.
The third knock was followed by Peggy saying, “Time’s up.”
The door opened. Peggy and Sandy were standing there. Both were still giggling and had mischievous smiles on their faces. Sandy stepped in, Debby walked out, Peggy closed the door.
“30 minutes,” Peggy said.
Sandy stood by the door.
“Just so you know, this was Debby’s idea. She told us about you and her having sex. She told Peggy and I about how gentle and caring you were with her. She wanted you for her birthday,” she explained. “Debby said she is okay with whatever happens between us. She wanted you to be our first time.”
“Thanks for explaining things to me,” I said.
I was surprised Sandy was here. Sandy’s parents were very strict. I knew that her parents didn't let their daughter’s date until 16. Then only in groups or chaperoned situations until they were 18. They didn't even allow boys into the house unless they invited them.
Sandy was very pretty. Her dark brown eyes and long dark hair, plus her light tan skin color made her look exotic. Her voice was a joy to listen to. When she smiled at you your heart melted. She was slim and petite. She had small perky breasts that were perfectly proportioned for her body. I could tell she was nervous. She stood by the door not moving or speaking.
“Sandy, it is up to you as to what happens during the next 30 minutes. I am not going to pressure you into anything. I will ask you before I do anything. You can say “no” or “stop” at anytime,” I assured her. I watched her face and body relax. Then she gave me that wonderful smile. The tension left the room.
“Thanks! Debby said that you were kind, gentle, and understanding.”
“What do you want to do first?” I asked.
“Let’s take off our clothes,.” Sandy said. I removed my shirt. “Wait I want you to take off my clothes, then I will take off the rest of yours.”
Sandy walked over to me and gave me a hug. I hugged back. My penis started to come to life pressing against my underwear and against Sandy’s stomach because of the difference in our heights. I untied the string holding up her blouse and it dropped to the floor. I hooked my thumbs under the waistband of her pants and pulled them down. She stepped out of them. I touched her shoulders, she jumped a little. Her skin was soft and silky smooth.
“Do you want me to continue?” I asked. She nodded. I reached around and unhooked her bra. I slipped the straps off her shoulders. Slowly her breasts were exposed. They were exquisite, they were not large, but were so round and perfect. I leaned over and we kissed. My hand came around to the front. I cupped her left breast with my right hand. She trembled at my touch. I started to pull my hand away, but Sandy grabbed it and pushed it back in place. I massaged her breast, then used my other hand on her other breast.
Sandy tilted her head backward. “That feels so good. Don't stop,” Sandy cooed.
My penis came to full attention. Creating a tent in my underwear. Sandy noticed and pulled my underwear down. They dropped to the floor. My penis popped out, pointing toward the ceiling. She starred for quite some time.
“May, may I touch it?” she queried.
“Yes, go right ahead,” I answered.
She slowly put her fingers on the head of my penis. She traced the curve of my member. From tip to base. It jumped, she giggled. She wrapped her fingers around my shaft and began stroking up and down it’s length. I continued massaging her breasts. I felt the blood pulsing against her fingers. I also realized the 30 minutes was disappearing rapidly.
I pulled her panties down and they fell to her ankles. With the same hand I reached down trying to find the place between her legs. Because of the difference in our height, my arm was not long enough. Realizing the problem Sandy gently pushed me back until I had to sit on the bed. I could now easily reach her pussy. She could still stroke me.
I traced the crack along her pussy lips. They were very warm and wetness was seeping between her lips. I noticed Sandy had also shaved her pubic hair as Debby had done. I pushed one finger between her lips. She was definitely wet. My finger slid easily the full length of slit. She cooed and moaned. I found her love button on the upstroke. She jumped “oooooo” coming out of her mouth. I circled her clit then ran my finger over it. She nearly collapsed to the floor.
Looking down at my penis Sandy said, “Do you think that will fit inside me? It is so big.”
“The only way to find out is to try,” I replied.
She pushed me down on the bed. I lay down on the bed with my penis sticking up in the air. Sandy crawled up on the bed and straddled me. I held her pussy lips apart as she lowered herself and guided me into her.
The head of my penis pushed against her. She pushed down several times. I continued to massage her breasts. Her nipples were now hard. I rolled them between my fingers. She pressed them into my hands. My penis had encountered a barrier. She pushed harder and nothing happened.
“My hymen,” Sandy said quietly.
“Take things as slow as you need to,” I said. “This is probably going to hurt some.”
“I know. My sister warned me,” she said.
I had to wonder what discussion she had had with her sister where this subject would have come up. I knew her oldest sister was married. Sandy pushed down. I could see the pain on her face. She pushed a little harder. I could feel it starting to give way. With one last push from her I slid farther into her. Sandy bit her lip and tears were in her eyes. It was good she was already wet.
“Hold still until the pain goes away,” I suggested. “We can stop completely if you wish.”
“It hurts and feels good at the same time,” she said. “Let’s give it a little time. It feels weird to have something so big inside me. I feel it pulsing inside me. The pain is slowly diminishing.”
A minute or so passed before she started moving again. Up and down slowly taking me more into her tight hole. I moved one hand to her clit and teasing it with my fingertips.
“Ahhh, keep that up. It helps the pain,” she instructed.
Soon I was completely inside her.
“Wow! You’re all inside me,” she said. “I can’t believe it. I feel so stuffed.”
She paused for several seconds then started slow long moves up then back down. I was in heaven. Sandy was so tight the sensation was incredible. Sandy increased the pace. I started moving in coordination with her. Her breathing came faster and shorter. I increased my pressure on her love button. Her head went back and she emitted sounds of great pleasure. I could feel my balls tighten.
“I am about to cum,” I warned her.
She said nothing, but increased the pace.
“5 minutes,” Peggy said from the other side of the door.
We paid no attention. I was not going to last much longer. I held off as best I could. The walls of her vagina clamped around me. I exploded into her. She came. Her orgasm shook her body. Her muscles spasmed around me. Sandy was barely able to contain her screams.
After several seconds she collapsed on top of me. I gave her a hug squeezing her body to mine. She was so warm. She was still breathing heavily. I kissed the top of her head. She lifted her head, inched up and we kissed. Her lips were soft, full, and smooth. We got up and quickly cleaned up. Sandy put on her top and pants. I put on my shirt and underwear.
“Time’s up,” came from the door as it opened.
Peggy, Debby, and Cindy were all standing there. Debby and Cindy stepped into the room. Sandy walked out smiling. Peggy closed the door.
“Cindy is very nervous about this,” Debby said.
“Cindy, it is your choice as to what happens. You can leave the room now if you wish,” I assured Cindy. “We will only do what you want. I will wait for your agreement at each step. You can say ‘stop' at any time.”
Cindy looked at me and then Debby.
“It’s your choice,” Debby said. “You can trust him to do what he says.”
We waited for Cindy to say something. Finally she said, “Can you put your pants on.”
I had forgotten that I was standing there in my underwear. “Sure!”, I said looking around for my pants.
They were in a pile in front of the bed with Debby and Sandy’s under wear. I picked them up and put them on.
“You can leave Deb,” Cindy said, still with a slight quiver in her voice.
Debby left. “We are giving you 40 minutes,” she said as the door closed.
I heard Peggy objecting to the additional time on the other side of the door.
“Please sit down on the bed,” Cindy said softly. I complied, leaving her plenty of room to chose how close to me she would sit if she decided to sit. She came and sat on the bed about 3 feet away from me.
“I was not expecting anything like this. I was just coming over for a birthday sleepover,” she said. “When Debby told me what she had planned, I was surprised, scared, and nervous. I have never done anything sexual, except alone by myself.”
“You don't know anything about me. Would it be alright if I told you about myself?” I asked.
“Deb just told me you were a nice guy and she likes you a lot,” she responded. “Go ahead tell me about yourself.”
“My name is Andy,” I started. “I am the oldest of 4 kids, 2 sisters and one brother. I live a block over and a block south from Debby’s. Debby and I were in the 1st and 2nd grade together, then she moved away. Peggy, Sandy, and I were in the same elementary school class through the 6th grade. We were also in the same Junior High. When Debby came back we were all in the same High School,” I told her.
Cindy then told me a little about herself. “I am Debby’s cousin. Her mother and my mother are sisters. I am an only child, like Deb. My parents got divorced about five years ago. I live over in the next city. Deb and I have been very close. I am about 9 months younger than her. I visited her in Chicago several times. I look up to Deb and trust her judgement,” she explained.
I took a good look at Cindy. She was really a slightly younger version of Debby. Same dishwater blonde hair. Same deep blue eyes. She was just an inch or 2 shorter than Debby. Her chest was just slightly smaller. She finally started to smile and relaxed a little.
“May I sit closer to you?” Cindy asked.
I nodded yes. She moved over next to me.
“Please put your arm around me,” she requested.
I put my arm around her. I flashed back to the times I had my arm around Debby.
“I'm sorry I walked in on you in the bathroom,” she said. “Sorry I starred. I had never seen a penis before, except in pictures.”
“That's okay. I understand,” I said.
She was quiet for some time. I sensed that she was trying to get the courage to say something. She fidgeted.
“Ah, do … do you think I could see your penis again?” she stammered.
I stood and took off my pants and then my underwear. I sat back down next to her. I spread my legs to give her a good view. She starred at it for quite some time.
“May … may I touch it?” she asked.
“Sure, go ahead,” I replied.
Hesitantly her hand moved toward it. She acted like it was dangerous. Her fingertips touched it and then pulled away. Then touched it again. She pushed lightly.
“It is soft and kind of spongy. How does it get hard?” she asked.
“It will get hard if it gets stimulated by contact or I see something that arouses me,” I told her.
She continued to rub my penis with her fingertips. I could feel the blood flow starting to concentrate there.
“Mmmm,” I said to encourage her.
“Does … does that feel good?” she asked.
“Yes it does,” I answered.
My penis began to get larger, but was still quite soft.
“May I wrap my fingers around it?” Cindy asked.
“Sure,” I answered.
She grasped it and started calmly pumping up and down it’s length. It began to swell. Her face showed some amazement. I sat still and enjoyed the pleasurable feeling.
“That really feels great,” I told her.
“What would you have to see to get aroused?”
“I do not want to push you to do anything You do not want to do,” I said. “But the first step would be to take your top off.”
Her hand paused as she considered my answer.
“Ok, but just looking, no touching,” she said removing her t-shirt.
I watched as her bra became visible. She had obviously done some tanning over the summer. There was a tan line just above her bra. Above the line her skin was a moderate tan. Below the line her skin was milky white. I smiled as I looked at her breasts. She nervously smiled back.
They were good sized, maybe a large C or a small D. Her bra was a little small. Her breasts pushed against the material.
“Do you like them?” she asked.
“Yes I do!” I answered. “Just look at my penis and then feel my penis.”
She looked down and then squeezed my penis. It had become longer and harder.
She smiled a bigger smile and said, “Did I do that?” I nodded yes. “Should I take my bra off?”
“Only if you want to,” I replied.
Again she gave it some thought. She reached back to unhook her bra. She was nervous and seemed to be having difficulty.
“Do you want me to help?” I asked.
She turned her back to me. I quickly unhooked her bra. I could now see the lines of the bikini top she must have worn while tanning. I slipped the bra straps off her shoulders. My fingers caressed her shoulders as I did so. She shivered. She held her bra in place with her arm.
“May I caress your back?” I became more bold.
“Yes,” she said without hesitation.
I ran my fingers back across her shoulders then up the sides of her neck. I massaged both sides just under her ears.
“Ohhh … that feels good,” she said. I continued for several seconds, before my fingers traveled down her back on each side of her spine. Again she shivered. I wanted to go lower, but decided against it. I went back up to her neck massaged each side at the base of her neck. Again she shivered, her skin had goosebumps.
“Are you cold?” I asked.
“No I just feel a little tingly,” came her response.
She moved her arm letting her bra fall to the floor. My fingers traveled down her back again. She reached back and found my penis. She went back to a slow, gentle stoke with her hand encircled around it. I stroked my fingers up both sides of her body, then across her collar bone to the middle of her back.
“Does it still get harder and bigger?” she questioned. Not waiting for an answer she asked, “Would it help if you massaged my breasts with your hands?”
“Yes, it would!” I responded. “Do you want me to do that?”
“Yes, if what I am doing to you feels good, I am sure that would feel good to me. Please be gentle, they can be very sensitive,” she requested.
“I will!” I assured her.
I moved my fingers across her shoulders and down her arms. I paused then moved to cup the underside of her breasts. Cindy drew in a deep breath. I moved closer to her. The tip of my penis touched her lower back. I leaned forward and kissed her shoulder. She shuddered. My hands moved upward to cover her nipples. They were hard and pressed into the palms of my hands. She took in another deep breath.
“Yes, yes keep going. It feels very good,” Cindy said.
I rubbed her areolas in circles around the nipples. “Oooos” and “ahhhhs” came from her lips. Her head tipped back in pleasure. Her eyes were closed and there was a smile on her face. I thought about dropping a hand down into her panties. I decided against it until she suggested it. Meanwhile my penis tapped against her lower back each time she stroked it. I was nearly at full length and hardness, but because I had already come twice I was not close to cumming again. I moved a little closer to her making my penis tap farther up her back.
Then Cindy said, “I have never felt like this. It feels so hot between my legs. Ah, my panties are getting wet.”
She abruptly stood. She pulled down her pants and panties. Since she was still facing away from me her rear end was in front of me at eye level. I reached out and touched her butt cheeks. She backed up slightly, so I grabbed them with my hands. I squeezed them both together then alternately. She pushed back harder, I went lower until I was rubbing between her legs. She opened her legs so I slipped one hand between them and reaching up to her pussy. I started at the bottom and moved along the outside slowly up to the top, then back to the bottom. I was surprised at the amount of pubic hair she had. I pulled a hair a couple of times. She twitched each time. Cindy was very wet. I could definitely smell her sweet, musky odor. I moved a couple of fingers up the crack between her lips. She moaned a low deep moan. She wobbled slightly. I moved my finger back down to the bottom of her pussy lips. I pressed my fingers between her lips and they immediately became wet. I moved to the top of her lips again. She jerked as I rubbed across her clitoris for the first time.
“Wow! Stay there,” she requested.
I circled around her clit several times with my fingers. She shuddered and trembled. I rubbed over her clitoris. Her legs gave way and she sat on my lap. My hand was trapped.
“Wow, I never felt anything like that,” she said.
My penis was “trapped” between us. She sat there for a minute or two. A knock came at the door.
“10 minutes,” came Peggy’s voice.
Cindy stood up almost immediately. She turned around. I got my first look at her gorgeous body and breasts. Her breasts looked larger than I had originally thought. She smiled at me. It was the same smile I had seen on Debby’s face a number of times. I smiled back.
“Not much time left! I am going for it,” she said as she took ahold of my penis.
She came closer and guided me toward her love hole. My penis touched her vaginal lips. With a slight adjustment I started to enter her. She paused. Obvious satisfaction took over her face. I wrapped my arms around her, encouraging her to go farther. She pushed down I encountered a obstacle. She winced.
“It’s going to hurt, at least for awhile,” I warned.
I could tell she was getting her courage up, readying herself for the anticipated pain. Her eyes and mouth closed. She pushed and almost like a pop her hymen gave way. I slid into her. She again was sitting on my lap, but this time facing me.
“Ouch, that hurt! I am going to get up,” she said. She started to stand up, but stopped. “That hurts too!”
“Just sit still. I am sure the pain will subside,” I suggested.
I stroked her hair, then her cheek. I put my hand behind her head, then I kissed her. I pulled back, but she moved forward giving me a seductive kiss. My penis jerked inside her.
“That felt good,” she said. “You are so big.”
She slowly started moving up and down. She was tight, but extremely slick. She began moving faster. I moved in sync with her. I grabbed her butt cheeks. Cindy began breathing fast and shallow. I could feel myself quickly reaching the point of no return.
“I’m going to cum soon,” I warned her.
She continued without interruption. I could feel her vaginal walls tighten around me. She breathed in deeply then held her breath. Her orgasm took over her body. She shuddered and jerked. She spasmed around my penis. I exploded inside her, ejaculating 3 streams into her.
She fell into me. Laying on top of me on the bed. Cindy panted, then slowly returned to normal. I hugged her enjoying the feeling of her soft skin pressed against my body. The inevitable knock came at the door.
“Two minutes,” Peggy said.
Cindy rolled off, stood up and walked into the bathroom. I heard the water come on. I stood and joined her. She turned, put her arms around me, and kissed me.
“Thank you! I never knew I could feel that way. Thank you!” she said.
She walked back into the bedroom. I cleaned up. I finished putting on my shirt and underwear just as Peggy opened the door. Peggy stepped in, Cindy walked out, Debby closed the door.
“30 minutes Peggy,” Debby said with amusement in her voice.
Peggy stood still for a few seconds.
“What are you waiting for?” she asked. “Get your clothes off!”
She removed her shirt and pants. I removed my shirt and underwear. She stood with her bra and underwear in place. Peggy was tall about 5' 11”. She had an athlete’s body, firm and tight. She was thin and muscled but not overly so. She had nice symmetrical B-cup breasts. Her legs were long and well toned.
Peggy had always been more aggressive than most of the other girls. She liked sports and joined in with the boys when we played games. Some would have called her a tomboy, but that would have been incorrect. She was very feminine. She was very pretty, not beauty contestant beautiful, but very attractive.
She stepped over to me. “What are you waiting for,” she asked. Take my underwear off!”
It was obvious she was not wasting any time. I reached around her and unhooked her bra and let it fall. I leaned over taking one of her nipples into my mouth. I used my thumbs to drop her panties to the floor. Her nipples were larger than those of any of the other three girls. I gently sucked and licked one nipple while I teased the other with my fingers. She pushed my head tighter to her breast. I sucked harder and give a slight pinch to the other. Before long she took my head into both her hands, pushing it up until our lips met. I hugged her close while our tongues explored each other’s mouths.
Her breasts were pushed up against my chest. Her nipples were hard and erect. My penis started to come to attention. It pushed up against her crotch. She spread her legs. My penis pushed up between them, rested along the crack of her vaginal lips. She closed her legs slightly “trapping” my penis. I could feel a warm liquid on the top side of my rod. It continued to grow and stiffen.
“Mmmm,” Peggy moaned. “Somebody is getting excited.”
She began moving her hips away and then back toward me. Very slowly and a short distance at first. More of the warm liquid covered my penis from the top then moving down the sides. I started moving in coordination with her, being careful not to slip out from between her legs. Peggy continued to moan and quicken her pace. My penis was well coated with her juice. It moved between her pussy lips.
It was a good thing I had already cum a few times earlier or I may have exploded right then. Then on one stroke the head on my penis rubbed up on her clitoris.
“Ooooo,” said Peggy as she jumped. “That sure felt good.”
She took my penis in her hand, rubbing it against her clitoris. She varied the motion and the pressure of the head on her love button. She shook and shuddered. After some time she jerked. My penis slipped into her love hole. Peggy paused. I paused. She pushed forward I went deeper into her. I had expected to encounter her hymen. I waited to start thrusting.
“What are you waiting for?” Peggy asked. “Don't you like this?”
“I don't want to hurt you,” I replied. “It can hurt the first time.”
“Are you worried about my hymen? I lost it about a year ago with the handle of a brush. It hurt for a day or so,” she explained.
Again she started moving her hips away and toward me. Peggy was tight. I pushed into her. She pushed back. Soon I was fully into her. Her vaginal muscles squeezed and relaxed on me. Then they rolled from the head toward the base of my penis. This was different than the feeling when the others had orgasms. This was controlled and deliberate.
“I've been practicing on my hairbrush,” she said. “You are so much bigger than the handle of my brush. It feels so amazing.”
Her eyes remained shut as she concentrated on what she was doing. I started moving out, then back in. She tightened as I pulled out and relaxed as I pushed in. I quickened the pace. Peggy grunted and moaned. I felt my testicles spasm releasing my seed into her. This triggered her orgasm. She trembled shaking from head to toe. It felt as if she was squeezing every last drop out of me. We held each other up.
We then went to the bathroom to clean up. Peggy wet a small towel, Turned around and began cleaning me. Soft, sensual, thorough attention started bringing my penis to life again. She handed the towel to me. I cleaned her with careful attention to her clitoris and love hole. My fingers strayed a few times to Peggy’s delight.
She took my hand led me back into the bedroom. She laid down on the bed. I laid down beside her, face to face.
“I don’t know how much time is left. Why don’t you put your head the other way,” she requested.
I flipped around so my face was in front of her pussy. She was looking straight at my slightly erect penis. The inevitable knock came at the door.
“10 minutes,” said Debby.
I felt Peggy’s fingertips on the head of my penis. They moved lightly around it’s circumference, then across the tip. It jumped, to Peggy’s delight. She continued moving her finger down the top to the base.
“Your hair is very coarse and wiry,” she said more to herself than anything.
I had reached forward and was using my fingertips on her pussy. I noticed she had shaved her pubic hair. I learned later that Debby, Sandy, and Peggy had decided together to shave themselves. I caressed down the outside of her lips then back to the top. Peggy squirmed. I moved down the crack between her lips then back up repeating this several times. I could feel the heat coming from inside her. I could smell a musky odor as liquid appeared from the crack. I pushed a finger into her, continuing to move it up and down. It slid easily with her lubricant. She pushed against my finger inviting me in deeper.
Her fingers continued exploring my rod. Rubbing up both sides, then down the underside. This felt amazing. I stiffened, bouncing with each heartbeat. Peggy moved down to my testicles exploring and caressing each one in turn. She gently scratched the underside sending me into ecstasy.
I was determined to return the favor. I pushed my finger deeper into her. I found her love button, I teased it with increasing pressure. Peggy jumped and bucked pushing her pelvis into my finger. I used two fingers to spread her pussy lips. Her pink clit was clearly visible. I put my head closer and tickled it with my tongue. She reacted immediately, pushing up against my tongue. She moaned in approval.
She shifted. I felt her warm breath on the tip of my penis, just before feeling her lips kissed the head. Soon her mouth encircled it. The warmth was entrancing. Her tongue licked the tip causing me to go to full size. She began taking me in deeper.
Her breath came in short puffs. Her muscles stiffened. Her legs squeezed together, causing my head to be forced back from her pussy. Peggy shook and spasmed reaching her climax. At the peak again the knock came at the door.
“Time is almost up,” came Sandy’s voice.
“Give us a second to clean up,” I replied knowing Peggy was unable to.
“Ok,” came a trio of voices, followed by giggles.
I stepped into the bathroom, cleaned up, then back to the bedroom as Peggy entered. I dressed completely. I went out to the main room. Debby, Sandy, and Cindy were all naked. Peggy stepped out still naked.
“Who do you think you are?” Debby asked. “Why do you have your clothes on?”
They surrounded me pulling and tugging until my clothes were all on the floor. I wondered was going to happen next.
(To be continued) -->
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