As I stood before the mirror getting dressed, I started having second thoughts about the agreement I'd made with my friend, Bianca. Hi, I'm Kate and I'm proud that although I'm almost 30, I still easily fit into size 8 dresses. The mirror revealed my great shape. Although I'm five feet ten, my physique is petit and my shoulder length straight blonde hair, blue eyes, beautiful smile and cute nose complement this slinky black dress that I'm wearing to the silly double date that I agreed to go on. I'm a 32-C cup which I think looks nice on a slender feminine figure.
Bianca's been my best friend since childhood and we studied together to become high school teachers, although the schools we now teach at, are on the opposite sides of the city. The main stress in Bianca's life is that she always seems to choose the wrong boyfriend and her relationships end in tears, which then leads to many hours of talking to me on the phone.
About a week ago, Bianca rang and excitedly told me that she'd met a young handsome lawyer. She was apprehensive because she knew that she wasn't good at judging men and she begged me to agree to go on a double date with them. My partner was to be his younger brother, who was also apparently studying law at University. The plan was that we'd go to a movie together and then to a nightclub for a while. Bianca wanted me to give her an honest appraisal of her young lawyer.
I met Bianca outside the cinema and told her that she looked really sexy. She'll slightly shorter than me and has larger breasts, which she was generously exposing in her designer outfit. It was obvious that she was excited about introducing her new Beau. When he appeared I was impressed; he was tall, handsome and wearing a beautiful suit. Behind him was his younger brother looking a bit embarrassed to be accompanying us.
Bianca said "Kate, this is Oscar. Oscar, this is my best friend, Kate."
We shook hands and I noticed the chunky Rolex he was wearing. He turned to his brother and said "My brother, Brad, has been looking forward to some time away from studying. Thanks for inviting him."
Bianca, Oscar and I stood chatting for a while with Brad looking awkward to one side. When Bianca and Oscar moved towards the cinema, I purposely stayed back a bit to talk to Brad.
"You really didn't want be here either, hey?" I said.
Brad told me that he'd been dragged kicking and screaming because Oscar had told him that his new girlfriend insisted on a double date. I managed to get him talking about his life and he seemed to be a genuinely intelligent, nice 20 year old.
The cinema specialized in showing art house movies and I had no idea of what we were going to be watching. The four of us sat in the back row and I found the atmosphere cozy. After the movie had been going for 15 minutes, I was finding that it was actually very enjoyable. Essentially it involved a love triangle between a man, his wife and his mother-in-law. Unexpectedly I felt Brad's arm drape over my shoulders and his hand settled on my right breast. I figured that it wouldn't hurt to give him some compensation for the night and besides, I could see that Oscar was doing the same with Bianca a few seats over.
While Brad settled into massaging my breast, I was annoyed that my bra was just a bit too thick and tightly fitting to allow me to get much pleasure from it.
I whispered into Brad's ear "I need to go to the bathroom, I'll be back soon."
In the bathroom I took my bra off and put it in my handbag. "He should enjoy that," I thought to myself.
When Brad's hand went back into place he obviously got a pleasant shock. He started concentrating on my nipple. He'd squeeze it and then brush against; the effect was electrifying. Both nipples became like pebbles and I was finding it difficult to concentrate on the movie, although the sex scenes grabbed my attention.
Brad must have spent an hour stimulating my nipple and squeezing my breast. I could feel the wetness in my pussy and a powerful need for an orgasm. In the darkness I felt over to Brad's lap and moved my hand against his impressive erection. I would have given him a hand-job but the movie was coming to an end and we were all going to have to walk out of here soon. I pictured in my mind what it would like; me with a big wet patch on my dress and Brad with an erect cock stuck out of his pants.
By the time the lights came on, I had managed to quell my lust to some degree and I saw that Brad's erection wasn't too noticeable.
Outside the cinema, Bianca told me that she wasn't happy with Oscar. She thought that he shouldn't have chosen such a sexual movie. With the four of us milling around, Bianca cancelled the plan for us to go to the nightclub and asked to be taken home.
Oscar had an impressive car and drove us all to Bianca's place. Brad and I sat in the backseat and glanced knowingly at each other while Oscar and Bianca argued outside.
When Oscar got back in the car he said "Kate, seeing we're not going to the nightclub, why don't you come back for a quick drink at my place and then I'll drive you home. It's only a few minutes away."
"That'd be great," I replied. As we drove to Oscar's place, the three of us chatted about the movie.
Oscar's apartment was magnificent. It was a penthouse with sweeping views of the city. It must have been 5000 sq feet in size and had polished marble flooring. Oscar opened a bottle of wine and the three of us chatted while drinking it.
"Excuse me for a while, I've got to go to my computer to check on the futures markets," he said.
As soon as he'd left, Brad leaned over and gave me a gentle kiss on the lips. He stood up and pulled at my hand to indicate that he wanted to take me somewhere private. The bedroom he led me to was spectacular.
"I'd like to suck your tits," he said and so I exposed them to him, which was easy since I didn't have a bra on. So there I was, standing in the middle of this bedroom with all the lights on, having my breasts sucked by a guy 10 years younger who I'd just met tonight.
He led me to the bed and gently lay me down. When my dress was lifted up, he didn't even take my undies off; he just moved them to one side to expose my pussy. I saw him drop his pants down and his cock was standing to attention with a little glisten from the precum that had accumulated.
My pussy was now dripping wet and I could smell my juices, "Fuck me Brad, I need your cock inside me, oooohh just fuck me."
He introduced his cock slowly and gently and I started bucking in an effort to get him deeper.
"Fucking hell, don't tease me with that thing, Fuck me," I said.
Brad then said, "This is only my third time fucking a woman and the other two were my age."
I begged him, "oooohh, just don't stop pleeeaase."
Brad was rambling about how good it was to fuck "a real woman." I was doing my best to get him to focus on me.
Suddenly he had his orgasm and I could feel his big cock spasm inside me. His cock just kept spurting and spurting and even when he withdrew, I could feel the hot semen spraying onto my dress, undies, pubic hair and legs. I looked down and saw a big mess with copious amounts of semen coming out of my pussy.
Unfortunately I was totally unsatisfied and as horny as hell.
Brad got dressed and got a few tissues for me to clean myself up with. It felt like he'd masturbated and I was just a bystander.
When we walked out to the lounge room, Oscar was sitting there drinking another glass of wine. Brad, who was looking pretty pleased with himself, thanked Oscar for the evening and said goodbye. He gave me a peck on the cheek and said he'd love to see me again.
When Brad had left, Oscar poured me another glass of wine. I was feeling so sexually frustrated that maybe the wine would help calm my body down.
"I don't think things are going to work out between me and Bianca," he said.
We talked for a while about Bianca and then he said, "But I'd love to go on a date just with you."
I must admit that I did feel attracted to him and after a small amount of chit-chat, I allowed him to come next to me and kiss me.
He wanted to take me to the master bedroom but I said, "I'm sorry but Brad has already cum inside me."
"But he didn't satisfy you, did he?" Oscar enquired.
"How do you know," was my reply.
"Because you were only in there a few minutes. It doesn't bother me if it doesn't bother you," he said.
He exposed my breasts right there on the lounge and started sucking them. Immediately I knew that he could satisfy a woman. He took my dress off and folded it. With just my undies on, he placed me on my front and started massaging my body. Oscar was funny and witty; he was also very slow in a pleasing way. He took his clothes off and then turned me onto my back. I looked down and saw a cock that was bigger than Brad's.
Taking hold of his hard cock, I rubbed it up and down the entrance to my wet pussy.
"I want your cock in my CUNT NOW," I pleaded, and with that he pushed hard into my desperate pussy until he was up to his balls in my cunt,
Oscar said, "God you are tight for a woman who has already been fucked tonight."
He slowly moved his cock in and out of my grateful cunt and lent over and kissed and sucked on my hard nipples.
"Oscar, aahh, please just give it to me harder." He took me at my word and started to pound harder and harder.
His cock was rubbing my clit so well that I could sense relief coming and several minutes later I had a massive orgasm.
After I'd recovered, I enquired "What about you?"
He reassured me, "I can wait a little while."
Before long he positioned me on my knees in front of the lounge. He sat there and pushed my head onto his cock. As my mouth was going up and down his shaft, my tongue was trying to stimulate him as much as possible. Oscar was reaching down and playing with my tits while I sucked him. It occurred to me that I was actually sucking Brad's semen off Oscar's cock.
Oscar was talking while I sucked, "A man can tell a lot about a woman by the way she fucks and sucks cock. Take Bianca for example. In the week that I've known her, we've had sex twice. She insisted that I wear a condom when I was fucking her pussy and she wouldn't swallow when I cum in her mouth. I don't want to deal with that shit."
Because my mouth was full of cock, I couldn't reply and he continued, "You're a good woman, a man can cum in your cunt and I'm sure that you don't mind swallowing a load of semen. I'll tell you this, this blowjob is a lot, lot better than those Bianca gave me."
As if to answer him I started playing with his balls and soon he was on the brink of spurting. He started groaning loudly as the semen shot into the back of my throat. I managed to swallow most of it but a small amount dribbled out of my mouth.
After talking for a while, having another glass of wine and looking at the beautiful city lights, Oscar drove me home.
"I'd like to see you regularly," he said.
"I'd like that," was my eager reply.
He added, "One last thing, because I'm a good older brother, would you mind fucking Brad every now and again?"
I was a bit shocked but I said, "I guess not, I suppose we've already fucked and he did spent over an hour playing with my tits."
So, that is how my relationship with Oscar started. Things got a bit kinky after a while – please let me know if you'd like to hear about those little kinky adventures with Oscar.