Rebecca was 22, tall and blonde, but was a virgin and had never been kissed because guys didn’t like her arrogant attitude. Whilst being very insecure on the inside, she portrayed a snobby personality and ‘looked down’ on others.

Her parents noticed this behavior and were concerned that it would affect her finding a husband. The family was very wealthy, and prided themselves on being the most perfect, rich family within their upper-class community.

Rebecca, however, was spoiling their image. She was rude, arrogant and came across as vain, as she was frequently spotted eating at extremely expensive restaurants and showing off by purchasing clothes from expensive stores.

So her parents decided to put a stop to the damage she was inflicting on their reputation. And they did so in a very unconventional way.

Her farther, Rich, contacted me, explaining that they wanted to teach their daughter a lesson, by humiliating her and enforcing respect. They wanted her to lose her virginity to prevent her from being a shy prude around potential suitors.

Rich suggested that my services could take place at their secluded country house, and that the whole family wanted to be involved in the process of degrading Rebecca.

I arrived at the country house a day beforehand to prepare. The property manager, Keith, let me in. Keith was a short, fat man in his late 50s with bad breath and greasy hair. Together we carried in my equipment at set it up in the large living room.

A bit about me – my name is Nathan, and I’m 30, tall, extremely fit, olive skin and wavy blonde hair. I have a six-pack and a large frame with well defined muscles. People say I look exactly like Cam Gigandet. But the most impressive thing about me is the size of my cock. It is 11 inches long and extremely thick. Probably almost as thick as a can of Coke. When it’s hard you can see the veins and the fat, round head turns purple. It also curves up slightly. Most women are unable to fit it in their mouths or take my entire length in their cunts. I’m just too big.

I was in the kitchen when Rebecca and her family arrived. They sat down immediately so that Rebecca wouldn’t wander into the living room. Keith served us dinner and Rich explained that I was one of his colleagues who would be staying with them for the weekend. Rebecca couldn’t take her eyes off me. She flirted with me the whole time and as I flirted back. I knew she was imagining me kissing her.

After dinner the family left us alone to get to know one another better. I moved to that I was sitting next to Rebecca and put my hand on her knee. “You are so beautiful” I said to her. She blushed and replied “you’re pretty good looking yourself”. I decided to lead her on a bit more and said “I’ve always imagined myself marrying a girl like you. I think you’re wonderful”. That was all it took for her to become completely infatuated with me.

“Now I have something I need to show you, but it’s a surprise so I need to blindfold you” I said. “OK, this is exciting” she replied. I placed the blindfold tightly over her eyes and lead her into the living room where her family were sitting on the large lounge at the edge of the room. I lay Rebecca down on her back on the “bed” I’d set up (a bit like a massage table), and locked her ankles and wrists to special cuffs on the table.

“Wait! What’s going on Nathan? I don’t like this!” she cried when she realized she was restrained. I took off her blindfold as Rich walked over to her. He explained how she was ruining the family’s reputation and how keeping her virginity was preventing her from finding a suitable husband. He told her that I’d been hired to solve these problems.

“So, Becca, you are going to lose your virginity tonight. But you get to choose who does it. Me, your 19 year old brother Zac, or the handsome Nathan?” he told her.
“Mum help me! Please help me” Rebecca sobbed. Her mother, Carol, shook her head and smiled, then said “Darling, this will be a horrible experience but it will do you good. And I am going to enjoy seeing you punished for your terrible behavior. Don’t try and fight us Sweetie. We’re doing this because we love you”.

I took over and said “So Bec, who do you want to take your virginity?” She started screaming and thrashing “No let me go! Don’t touch me!” So I got a ball-gag and inserted it into her mouth. It was the kind where you can remove the middle so you can insert a cock inside her mouth without her being able to close her jaw or bite. I left the middle in for now.

“Ok I’ll choose for you. I will take your virginity, but your father might get the honor of deflowering your beautiful, virginal anus”. The look of horror on her face was priceless.

I cut off her clothes and re-adjusted the bed so that her legs were spread very wide and I could access her pussy standing up (the bed split down the middle between her legs and the sides swung out). I groped her large milky-white breasts firmly which made her wince. I tweaked her nipples hard and dragged my fingernails down her stomach.

“I get to be the first person to see between your legs don’t I?” I said. She continued crying.
In a very clinical manner, like a doctor, I examined her pussy. Pulling her lips apart, stretching them, looking at her vaginal opening carefully. I used one finger to press down on her clit. Rebecca was red in the face and I could tell she was completely humiliated and embarrassed. She was about to be violated and I knew she was soon going to feel very angry.

I put my index finger in my mouth then suddenly stuck it into her vagina and curled it up so I was firmly massaging her g-spot. “Ahhhhhhhhhhh” she moaned/cried in surprise and pain.

“Oh don’t be a sook Becca” said her mum. “I know a finger can’t hurt that much”.
I said “True, but I’m aggressively rubbing her g-spot so this is probably the first time she’s ever felt such intensity inside her pussy. Although it’s very dry so it probably is a bit painful. Shall I lick you Becca? It might help you get wet”. The thought of having a man’s mouth make contact with her private parts terrified her.

I bent down and spat on her clit. Then began lapping at it like a thirsty dog, running my tongue from where my finger was inside her pussy up to her clit, over and over again. “Ahhhhhhhh…eeehhhhhh” she protested, feeling violated by the strange sensations. She was getting mad.

“Ok we can do this two different ways” I told her. “We can fuck you with a series of dildos that progressively get bigger and are designed to dilate your pussy. It will be a very long process and will eventually end with you being stretched wider than a fist.” Rebecca squealed through the gag, tears running down her face. “Or I can fuck you right now, without any dilation. Just my cock straight into your virgin pussy.”

“I’d enjoy watching the dilation process” said her Mother.
“No, just fuck her right now, nice and hard. I want to fuck her ass as soon as possible” said her Dad.

“Ok Sweetie, lets allow my cock to take your virginity shall we?” I decided. Panicked sounds came from the gag and her eyes were wide open. She shook her head and pleaded with me using her muffled moans.

I stripped my clothes off, revealing my ripped muscles. I rested my massive purple cock head on her pubic mound, which was covered with a thin layer of blonde hair. I made a mental note to remove that later. My cock rested on her and came passed her belly button. I doubted she’d be able to take much of me inside her.

With my fingers I parted her lips and then ran the tip of my cock up and down her slit. It was slightly moist from my licking but I could tell that she was going to be quite dry inside, not enough to be painful for my cock, but enough that it would be extremely unpleasant for her.

“Ok Bec, now I’m going to push the head of my penis past your labia and into your vagina. Don’t worry I’ll stop when the head is in”, I explained to her in a clinical manner that really turned me on.

I pushed my head into her pussy and it was as tight as a vice. She screamed as if I was trying to force a pineapple up inside her. The sight of my cock head inside her was beautiful. I stood there so her dad, Rich could come over and take some photos of me inside her, and the painful expression on her face. This angered Bec even more, seeing her father enjoy the humiliation and pain she was feeling. She felt angry and betrayed.

“Ok Bec, with the next move I’m going to insert my penis as far as I can until it meets resistance. It’s going to split your hymen which will be extremely painful. You’re going to feel your inner walls stretch to their limit and a lot of pressure on your cervix. Are you ready”. More screaming came from the gag in her mouth.

I placed my hands on her breasts for grip, and thrust my hips forward, plowing my 11 inch thick rod into her tight virgin pussy. Her shrieks were deafening and her whole body tensed up, as if she was convulsing with pain.

I hit her cervix, but I my cock was only half way in. “Now Bec, you’re no longer a virgin, and I’m going to have sex with you. I love the way you scream, it really turns me on. You’re so tight this must hurt a lot for you. Fucking you is going to be like fucking a child”

I began thrusting in and out of her blood soaked pussy, hitting her cervix everytime. Her brother Zac was jerking off, her mother came over and started biting and sucking Bec’s nipples, and Rich stood there with one hand on a video camera, and the other stroking his 9 inch dick that was oozing pre-cum.

I reached forward and pulled out the middle plug of the ball gag, so that when Zac and Rich were ready to cum, they could shoot their hot sperm into her mouth.

“Now Bec, this is feeling really good for me, but it could be better. I want to be able to fit the entire length of my shaft inside your cunt, but the only way I can do that is my penetrating through your cervix and fucking your uterus. The cervix is where babies come out, so it’s going to hurt a lot when I open it with my cock. And it’s going to feel so good for me that I’ll most likely come inside you, impregnating you with my child”

And with that I pulled out of her pussy completely and thrust with all my might into her cunt, piercing through her cervix which felt absolutely amazing. A lot like passing your cock through a child’s anal sphincter.

Bec passed out from pain.

After 10 strokes I shot a massive load of cum into her uterus. Her Dad came inside her mouth, followed by her brother. She was going to wake-up to a very sore pussy and a mouthful of her family’s semen.

(To be continued)
The next chapter will involve incest and forced anal. Please tell me what else you would like me to include.