"I'm almost ready!" I shouted as I prepared to go down the steps in my new skirt. I was ready to go to dinner with my mother and Henry. It was a double celebration because it was my 16th birthday.
I laughed as I looked in the mirror. A year ago I was a skinny, flat-chested, pimply faced kid. My acne was gone, my hair was long and my breasts grew to a large C cup. My mother noticed that my curves sprung up overnight seemingly. I admired how my new dress showed off my new boobs. My face bore a striking resemblance to Jessica Simpson. I was quite the hotty. Many boys in school wanted me but I was not interested.
On my 16th birthday I was still a virgin. I had no desire for any of the boys in my school. They were all just kids. I was going on a date with my mother and Henry. My mother was single because my father ran off before I was born. Henry was an insurance agent she met through a friend at work.
Henry was a very nice man. He was financially very well off. From the looks of him he spent his extra money on food. He was very kind but at 5' 8" and 300 pounds he was not attractive. I was just pleased that mom was happy. Today we were going to a fancy restaurant to celebrate.
When Henry arrived I was ready but mom was not. Henry sat next to me and told me I was a knockout. I thanked him as he moved closer. My mom then came down the stairs and we left. I thought Henry was staring at my boobs when he and I were alone waiting for my mother. I thought I was being silly and we went to dinner. During the dinner my mother excused herself to the bathroom. Henry moved closer to me when my mother left.
"My, my Jessica. You certainly are blossoming into a very pretty girl. Have you been told you resemble that other Jessica? You know the pop singer? You must have many boyfriends."
"No. I don't need any," I replied innocently.
"Surely, you like men?" he asked.
"What do you mean?" I asked like a fool.
Henry moved closer. "I can't help myself," he whispered as his eyes scanned the room for witnesses. Henry moved towards me slowly and put his hand on my left breast. "Don't you want a man," he whispered while looking about the Restaurant. He began to gently massage my breast.
I reached for his hand and he caught it and put my left palm onto his crotch.
"Haven't you ever wanted this?" Henry squeaked while pushing my hand into his groin. I could feel the tip of his hard penis on my palm. "I want you bad," the fat man panted as he held my left hand on his erection with his and his right hand inched up my skirt. "Those legs, that body. I need you," Henry moaned.
I didn't know what to say. My mom quickly returned to the table. She didn't see what Henry was doing to me. The conversation turned to current events but I thought to myself. I felt I should tell my mother but I didn't tell her. In some odd way the thought of exciting Henry turned me on. I knew he was fat and about 40 years old but in some odd way I liked it. That was the first time I had even come close to touching a man and I liked it. My panties were soaking wet for the first time ever thanks to this man.
I thought it was over for tonight. I was wrong.
"Henry could you stop at the store on the way home? I need some things," Mom asked.
"Sure thing," Henry said as he pulled in.
Mom jumped out of the passenger seat telling us she would be back soon. Henry invited me up to the passenger seat. I agreed and moved up. "You are a virgin aren't you?" he asked.
"Yes," I muttered.
"Oh my god!" He exclaimed as he placed his hand on my breasts again and moved a hand under my skirt. I instinctively moved myself away from him and looked around the grocery store parking lot to make sure there were no witnesses. He grabbed his zipper and unzipped his pants. "Please, just rub me." he begged. "Please!" he yelled as he pulled my hand to his hard penis. He reclined his seat and produced his cock from his zipper hole.
I never looked at it again. I scanned the lot for people. I didn't say a word but started to slowly play with his rigid penis. I grew hot and flush while touching him.
"Oh, Jessica! Keep going." he muttered.
I continued stroking with my left hand as his right hand reached inside my bra and he fondled my sizable breasts. "They are real! I thought you stuffed your bra. Holy shit you are stacked." he muttered.
I continued my work not looking at Henry. After about 30 more seconds he began to buck. "Oh!" he shouted.
I felt him squeeze my left breast as a hot liquid filled my hand. Henry had ejaculated all over. I gave him a few more rubs and removed my hand to see his white sticky cum all over it. I grabbed a few tissues from the console and cleaned it up.
Henry was sweating profusely. He produced a handkerchief and cleaned his pants. He told me how nice it was for him for the next 5 minutes and begged me not to tell mom.
My mother returned and Henry dropped us off at home. "Henry, before I go do you feel well? You look sweaty and your face is beet red," Mom asked him.
"I'm fine. Just a little warm outside. See you later ladies," he said as he sped off. I went to my room and thought of what happened.
I made a grown man cum. He had been with many women and he liked me. I liked the idea that I excited his cock. I was looking forward to our next encounter.
I had spent time with Henry since then but we were always with my mother until gardening day. My mother was gardening when I was dropped off. She worked out back while Henry was doing the weeding out front to help. When I passed Henry I pretended not to notice him.
After ensuring that mom was busy out back, Henry glanced at me and scurried after me into the house. I was wearing a tank top and shorts. I had just spent the night at a friends house and been dropped of by her mother. I heard Henry behind me but made no move to speed up.
When I arrived in my room Henry closed the door behind me. "I need you," he said.
I didn't respond.
He tried to kiss me but I gently pushed his face away. I sat on my bed. Henry knelt at my feet, pulled up my tank top and began kissing my stomach. I laid back on the bed as he slowly moved towards my shorts. Henry parted my legs and pulled my baggy shorts down to my knees. He left my underwear on and pulled it to the side exposing my juicy vagina to a man for the first time ever.
Henry pulled me closer and inserted his moist tongue. I felt it touch my clitoris and felt an overwhelming pleasure. I never knew a tongue could do so much. I involuntarily caught myself grinding my crotch into Henry's face. I had never felt pleasure like this before.
"You are so hot and wet!" Henry whispered.
I felt a like something inside myself was going to explode. Then I felt an intense pleasure. I grabbed Henry and pulled his head closer while his pudgy hands squeezed my still clothed boobs. I surprised myself by letting out a moan.
Soon the moment was broken. "Henry, I need your help out here," my mom bellowed from the backyard.
Henry stood up and wiped my love juices from his face and whispered, "I'll be back," as he left.
I couldn't believe it I just had my first orgasm with Henry's tongue.
I cleaned myself up and Henry returned to my room. Mom was still out back. He grabbed my wrist and pulled me into the bathroom. Once there he fumbled with his belt and dropped his pants to reveal his tented underwear. From the bathroom window he could see my mother and she would only see his face.
"Get on your knees or your mother will see you," he ordered.
I obeyed and knelt out of the sight of mom. He pulled down his underwear as he sat on the toilet. "Take it in your mouth," he whispered while pulling my hand to his flaccid cock.
This was the first time I had seen his penis outside of his pants. Henry's penis was about 4 inches long but rigid as a rock. I slowly stroked it but Henry grew impatient.
"C'mon Jess, suck it," he ordered as he pulled my blonde mane of hair closer to his big belly.
I slowly ran my tongue around the mushroom head of his penis while he shivered in delight. I put his penis in my mouth and started moving back and forth.
"Mmmm," he moaned softly.
I had no problem fitting all of his shaft in my mouth. He held my hair tight to his crotch with one hand while the other hand reached underneath and grabbed my boobs.
"Oh my god. You are gorgeous! Swallow it. Swallow my cum!" Henry moaned as he pulled my hair and pumped faster and more violently. He held my head down and I felt his hot, salty semen hit the back of my throat as he held my face into his sweaty crotch.
"Swallow it baby," he ordered as he pumped a few more squirts into my mouth. I gagged and tried to spit it out but he just kept telling me to swallow.
Eventually, I swallowed all of his cum while fighting back the urge to get sick. Henry quickly cleaned himself and left the bathroom with me on my knees gagging. I stood up and went to my room. I had a plan for next week. Henry's birthday was going to be a day he never forgot.
The plans were for Henry to pick me up at 4:00 and bring me to my mother's place of work. When mom was done at 4:30 we would go out to dinner. I arrived home from school at 3:00 to find Henry waiting for me at the front door. After letting Henry in he immediately made a grab for me but I surprised him by stopping him.
"Go into my bedroom and take of all of your clothes. I have a birthday present for you," I told him.
Henry looked stunned. He stared at me vacantly but complied. I went to my mother's room and took off my clothes. I put on a sheer negligee of my mothers. It was white and outlined my large breasts and my hard nipples poked through the material.
I told Henry to lay on his back and close his eyes for his surprise. He did and I saw his small cock was fully erect. I approached him and gave his penis a few strokes. I proceeded to put a condom on his penis head an roll it down. Henry quivered with anticipation. I then climbed onto his large frame while holding his cock in my hand.
I gradually lowered myself onto his prick inch by inch. I couldn't believe I was giving my maidenhead to a fat and older man but it was too late to turn back now. I soon engulfed every inch into my now dripping vagina. I felt a little pain so I was a bit tentative. Henry would have none of it and pulled my waist tight to his little prick.
I wanted to move more slowly so I pulled away. Henry rolled me off his fat body and onto my back. He immediately jumped on top of me using his large frame to spread my legs as far as they would go. I didn't want this. I tried to fight him off but he was way to heavy for my 115 pound body.
"I must have you!" he yelled as he bucked wildly his penis in and out of me. He pulled out for a second and I saw a chance to escape. He was reaching down to pull off the condom! I could get pregnant.
I tried to break away from Henry and rolled to my stomach. He pulled my leg back and placed his heaping gut on my back. He had me pinned on my stomach. He pulled my legs off the bed and moved between them forcing them open. I was now face down with no leverage while Henry's feet were on the floor and his weight rested on my small frame while he had my legs parted.
In short, Henry had access to my unprotected cunt and there was nothing I could do to stop him! I felt him reach under and put his cock head at the opening of my cunt. "Hot 16 year old cunt. You show your tits and ass to everyone and don't give it to anyone." He yelled as he bucked violently.
I shouted "OH!" in pain with every hard stroke as his fat body slapped against my ass. He grabbed my swollen breasts in his pudgy hands and clutched them very hard.
"You put these in our face and expect us not to fuck you! Well I am fucking you! How do you like it?" He shouted again.
I kept crying out in pain with every hard stroke. My yelling only served to excite him. "I'm gonna fill your cunt up with cum, you whore!" Henry insisted. He bucked a few more times and yelled loudly and with one final thrust ejaculated into my virgin pussy.
I tried to move but he laid there for a few minutes letting his monster load of semen drip down my leg. Then I heard a scream.
Henry and I shot up to see my Aunt Angela. She ran to the phone and called the police while Henry hurriedly dressed and ran away. The police caught him at his house and he was sent to prison for 2 years.
I never told anyone about the other times with Henry. It would have only served to get him in more trouble.
Mom was crushed but I am okay with it. She has started to date a new man now. He works with her and he's black. I guess its time to get more short skirts and tight tops.