Friends Sister – Session 04 – Date With Emily

It was one week since Margaret left and Susan and I fucked like rabbits in all the time we got with our summer jobs going on. We both fucked on the couch in the pool, in the laundry room with her on the washing machine, in the shower and of course in the bedroom.

Then one morning as we were having our breakfast after a really intense makeout session Susan asked me “Would mind helping me with something?”

“Of course sweetheart” I replied.

“I know I’ll be asking a lot.” she said.

I cut her off saying “Just tell me what is it?”

She spoke very hesitantly “So you know I have a cousin Emily, she lives half an hour drive away and well I want you to help her.”

I vaguely remembered seeing Emily at Andy’s funeral but didn’t quite recall her as I was mentally disturbed at that time. Anyway if Susan wants me to help her I would surely help her.



“What kind of help does she want?” I asked.

“Does she want help with assembling furniture, or other household stuff?” I asked again.

“No, it’s actually she hasn’t had a very good experience with boys in high school, this has given her a confidence problem and she has built a shell around herself, I want your help in breaking her shell.” she said.

“You want me to set her up with a guy or something?” I asked her with raised eyebrows.

“No actually she wouldn’t trust any unknown guy and since she knows you well through me and Andy even though you guys haven’t met, she kind of trusts you.” Susan said very hesitantly.

“You want me to take her out for a date, like a romantic dinner?” I asked very cautiously.

“Yeah and a small thing more.” Susan said in the same hesitant voice.

“What?” I asked casually.

“You see Emily is actually very socially embarrassed due to the fact that she’s still a virgin so-” Susan said but I cut her off.

“FUCKING SHIT! You want me to have SEX with her!?” I almost shouted.

“Yeah,” Susan said now looking away from me.

“But babe how can you even suggest this?” I asked very gently.

“Why not hon, you are a nice man and I wouldn’t trust anyone else with Emily with the amount of jerks she’s been through already.” She said with pleading eyes.

“Alright, but what about us?” I asked.



“Believe me babe, I have no problem with this as Emily is my best friend and I want to help her become free from the social awkwardness she’s been facing all these years.” Susan said with a pleading note in her voice.

“Ok, I’ll do this if it makes you happy.” I said and went up to kiss Susan and said “But remember it I’ll be you I will always love.”

“Aweee thank you so much baby, I’ll just tell Emily you’ll pick her up at 7 in the evening.” she said fishing out her phone from her pocket. The rest of the day went with Susan preparing me for the date, telling me about Emily, her likes and dislikes.

It was decided that I would take Emily for a movie followed by dinner and then bring Emily to our house and Susan would be bunking with a friend of hers for the night. Exactly at 7 pm I rang the doorbell of Emily’s flat and my eyes popped out when a curvaceous brunette with a slim figure, F cup tits and a gorgeous ass introduced herself as Emily.

“Hi Ralph, I’m Emily.” she introduced herself with a charming smile.

“Nice to meet you Emily.” I responded and proceeded to hug her making her blush with apparent excitement and embarrassment. I took Emily for a movie so that she would relax a bit and it would also give her time to get accustomed to me.

But it turned out to be a disaster as the movie I picked without much research turned out to be a spine chilling horror film which we had to leave midway as Emily turned quite pale and cold with just 10 minutes into the movie and I feared she would pass out. I then took Emily to a game arcade where she enjoyed herself and eased up a little bit.

After leaving the game arcade Emily and I went to an Italian diner where we had an amazing dinner accompanied by wine we got using fake ids. The wine had it’s effect and Emily got quite giggly as I drove us back to the house. As we entered the house I could see Emily getting stressed up again so I made her sit on the couch and then proceeded to give her a massage by the end of which she relaxed again.

I then sat beside her on the couch and we talked about our lives with each other our life and other stuff for an hour at least. By this time Emily’s head was resting on my chest as I caressed her back.



I slowly preceded by kissing her head, behind the ears and on the neck and cheeks until I finally claimed her lips with mine. She responded to my kisses with fervor and kissed me back with her eyes full of blazing passion. I slowly undid the zipper of her dress and pulled it down to reveal her glorious tits.

She stood up, completely removed her dress and sat down on the couch again as I started eating out her clean shaved pussy. My tongue circled her pussy lips and stroked her clit as she screamed with pleasure. My tongue was too much for her virgin pussy and soon she came so hard that her whole vibrated and I had to keep her from falling off.

She then pushed me on the couch and she removed my pants and boxers to reveal my massive cock.

“Oh god! This is going to impale me.” she exclaimed.

“Don’t worry, I’ll be very gentle with you” I said reassuringly.

She smiled wickedly and instantly swallowed my cock in one go as I gasped with pleasure. She started licking me very slowly, massaging my balls at the same time making me squirm in my seat. I felt my balls churn instantly and realized I was close.

“I’m gonna cum!” I exclaimed as she increased her pace and I finally blasted off into her mouth.

I knew I had cum a lot as saw my cum leaking out of Emily’s mouth as she struggled to swallow it. After she swallowed my cum, she sat beside me as I kissed her again.

“Let’s take this to the bedroom,” I said as I scooped her up my arms making her blush.

I laid her my bed and kissed her pinning down her body as she gasped and moaned with pleasure. After kissing for a while I turned us on the bed so that she was above me.

“You control the pace.” I told her as I directed my cock into her. She very slowly took my cock into her pussy as she gasped and moaned as my cock went inside her.



Once I was fully inside her, she started riding me very slowly and steadily and she came surprisingly with my shaft still inside her. I was astonished to her riding me with intense vigor and passion for a virgin as soon as she recovered from her first orgasm. The pace of our love making coupled with the tightness of her pussy was too much for me and soon I felt close to cumming.

“I’m gonna cum” I shouted as I pinched her nipples making her scream.

“Aah, Yes me too baby” she replied as increased the rate of her pounding.

Both of us couldn’t take in any longer as we came together embracing and kissing each other. The orgasm was so intense that Emily dug her nails into my back drawing out blood.

We both fell into heap with Emily on top of me as we came down from our orgasms. We both instantly fell into a deep sleep still hugging each other as my cock slid out of her and cum started seeping from her pussy.

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