My Sister's Girlfriend

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Brother is asked to have sex with his sister's future wife.
6.4k words
4.55
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Part 1 of the 4 part series

Updated 06/09/2023
Created 06/09/2018
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Nikkiejanes
Nikkiejanes
1,456 Followers

I was round at the house my twin sister Janet shares with her new fiancé Jill, having a beer and trying to sort out the wedding arrangements, especially as our parents could not accept that Janet was in a lesbian relationship with Jill.

Both girls are stunning, I would fancy Janet, if she wasn't my sister, she is about five feet five, tall has a small frame with something like 32B boobs, a narrow waist, slim, toned legs, shoulder length brown hair that frames a pixie like face with green eyes.

Jill is equally gorgeous and I would definitely make a play for her if she was straight, she is a couple of inches taller, 34B boobs, slightly chunky legs, a nice taught ass, dark nearly black hair that hangs midway down her back, a cute heart shaped face and deep blue eyes, that sparkle when she laughs, which when she's with Jan is a lot.

They have been together as a pair for two and a half years now, Jill has always been gay but Janet went out with guys until she realised that she wasn't really interested in them. I've always accepted Janet's decision but our parents totally freaked when she came out, I've tried to ease things for both of them over the last couple of years, but they are still undecided about the wedding.

I'd just sat down with a beer when Jill shocked both Janet and me with what she said.

"Janet I want to fuck a man before we get married. I just want to try it one time."

Both Jan and I looked at her amazed, she had never given any inclination that she was interested in men in a sexual way before, then she shocked us both even more.

"In fact I want to fuck John." (Yes our parents did call us Janet and John).

"WHAT THE HELL DO YOU MEAN YOU WANT TO FUCK MY BROTHER!" screamed Jan at her. "What if he got you pregnant?"

"If he got me pregnant it wouldn't matter, in fact it would be great, also if I'm having a man Johns is good looking so it wouldn't be a hardship."

"What the hell do you mean, you'd be happy if he got you pregnant?" screamed Janet at her again.

"Jan, you know we've been talking about me having a baby for ages, well this way we don't have to get a donor, and if he did get me pregnant, it would be almost like you would be the father as it would have your DNA and genes." Said Jill in reply.

It came as a shock that Jill wanted the baby as she is the more dominant one in the relationship.

"Looks like you've thought this out, why didn't you talk to me about it first before blurting it out like this?" Jan said to her.

I'm sitting there stunned as they have this conversation about me fucking Jill and giving her a baby, then I said. "Mum and Dad, would totally cut us both off if they knew I'd got Jill pregnant, I'm only just getting them to accept you two as a couple after all this time." I said to Janet but the idea was intriguing me, it would be no hardship to fuck Jill.

Both girls were staring daggers at each other and I thought that Janet would call the wedding off, then she said. "If Johns okay with it, how would it work, how do you do it? But let me say I'm not happy or comfortable with the idea for my little brother having sex and getting my fiancé pregnant."

"I've not thought it out that much." From Jill.

"Jill, do you just want sex with a man for one time to see what it's like, or do you really want me to get you pregnant?" I asked.

"Both."

"Well there's the problem, one time might not do it," I said "also I'm not sure I want to get involved with this, I need to think about it. Yes I would love to have sex with you, your gorgeous but the pregnant bit I'm not sure of, also I don't want to upset Jan. We all need to think about this."

The following week I'm back at the girls place and have made my mind up. "Okay girls," I said "I'm willing to give this a try but on the following conditions. One: Jill, we have sex for one night, nothing is off limits to me, that's the sex with a man part, if you're doing it your doing it fully. Two: If your okay with having sex with me, then we try for twelve months to get you pregnant by having sex and that will mean more than once a month you know. Three: if after twelve months you're not pregnant then we look at me being a donor."

Both girls looked at me in amazement at what I had proposed, more the fact of the number of times I had said Jill would have to have sex with me. Well there had to be something in it for me and as I said Jill is stunning.

Jill said, "Okay; I think, how does the sex go though?"

"We have sex in every way for one night, vaginal, oral and anally, you can hold nothing back, if your having sex or fucking me that's what the deal is. I will be gentle with you, but you have to commit to this and go all the way." I wasn't sure I meant all this I wanted to see how far Jill would go.

"No fucking way brother!" from Jan.

"Well; okay I guess. It's my suggestion and if I'm going to have sex with you and experience a man it should be in every way." This from Jill, "What about the pregnancy thing then?"

"We don't know how long it would take to get you pregnant it would probably take more than one go, so if you're okay with sex, we have sex in a planned way when you're on the fertile time of your cycle. If you don't like sex with me fine, I'll donate but I want both of you girls with me when I give my donation. I'm putting a time limit on it as I don't want this to get too kinky and to screw up your relationship. "

"OK, I'm happy with that." Said Jill.

Janet was looking daggers at both Jill and me. "I'm not happy about this at all, you seem very keen to fuck my fiancé John."

"Look Jan, Jill asked for this not me, I've just come up with a way to make it work, and I did say if Jill doesn't like the sex then that's it it's just the one night. Anyway she is stunning so I would love to have sex with her, but you both have to be ok with it."

Jill said, "Jan I'm supposed to be the female in this relationship, you've fucked men so I feel I need to do it at last once. We both agree we want a baby, so John is perfect. I don't want any anonymous donor as the father of our child."

Jan was still not happy and wanted to think it through. After an hour she grudgingly said. "Ok you two go ahead and fuck. I agree that John would be best option as a father, but on one condition, I want to be in the room for your first night."

"Whoa"! I said "I'm not into public performances and your my sister."

"That's MY condition for this, anyway I'm not joining in I just want to be there for Jill. I need to be there, please."

"MY condition, I get to watch you girls get it on at a later date."

"No way!" from Jan "I'm not putting on a sex show for you."

"You want me to do that for you so fairs fair." I replied. Things were heating up between Jan and me and if Jill hadn't interrupted we may have had a big falling out.

"Jan, it's only fair, if you watch John and me, he should be allowed to watch me and you, anyway I think it would be sexy to perform for your brother. I've always fancied a bit of exhibitionism."

"John, lets get it on. Tonight, now I'm ready, I don't want to wait, all this talk of sex has me horny. Jill put up or shut up. I'm going to fuck John NOW!" As I said Jill is the dominant one.

I hadn't expected that Jill and I would be getting it on so fast but I was not going to turn down an invitation like that.

I got up took hold of Jill's hand and led her to their bedroom, I left the door open so Jan could come in when she was ready. I took Jill in my arms and bent my head to hers and started to kiss her, strongly and passionately but not in a possessive way, at first she stiffened and did nothing, then slowly, hesitantly, she responded to my kisses pushing her tongue deep into my mouth and playing with my tongue. Boy could she kiss, Jan was a lucky girl if Jill kissed her the same way.

I could feel Jill trembling as I ran my hands over her gorgeous body, pulling her in close to me, she could feel my excitement as we came close together as my cock had sprung to attention as soon as she responded to my kisses. I grabbed her ass and pulled her tight to me and ground my hips into her but she broke away slightly so that our legs were inter twinned and started to rub her pussy against my leg.

I moved my hand to the zip on the back of her dress and slowly lowered it until it would go no further, then as I moved away from her the dress fell to the floor and she stepped out of it. I kissed my way down her neck and shoulders until I was level with her boobs which surprisingly seemed to droop a bit, I soon found out why. I cupped her left boob and it was full and heavy, as I tweaked and teased the nipple I dropped my head to her right and sucked it into my mouth as far as it would go, then sucking on it all the time slowly let it come out of my mouth.

We heard a gasp from behind us, Jan had come into the bedroom and was watching us. "Oh you look good together, John make love to her for me please!"

I slowly ever so slowly kissed my way down Jill's trembling body until I was level with her hips and looking at her white lacy panties, I kissed her mound through them gently teasing it through the material. Jill stopped me pulled me up to my feet then stripped me of my clothes grabbing hold of my cock for the first time, "Oh my God it seems so big." She said.

Then she pushed me down to my knees again. This time I took her panties in my hands and pulled them down her firm thighs exposing her pussy to my view for the first time. The outer lips were very dark in colour and I could see she was already wet, I eased her lips open and gazed at the pink inner before pushing my tongue deep into her, burying my head into her, she had a soft musky smell and tasted divine. I played my tongue up and down her pussy for what seemed like ages as she became more excited and began to grind her hips hard into my face.

She moaned "that feels good, just keep doing that." I wasn't going to stop I was enjoying her too much. I heard another gasp from my sister Jan at this point.

I'd found Jill's clit and began to tease it mercilessly flicking it with my tongue, then sucking it into my mouth and rolling it around, Jill was squealing with delight and kept pulling my head hard into her. I could sense she was coming to a climax as her breath started to pant and her hips were thrusting into my face with increasing ferocity, then with a shudder and soft moan she came and a wave of her juices flooded my mouth, she was sweet and sticky and tangy in taste, I loved the feel of her juices on my face and her taste in my mouth.

I wasn't going to let her come down from her orgasm too much so pushed her onto the bed spread her legs wide and positioned my cock at the entrance to her pussy pushing in slowly until I could feel the resistance of her hymen. I stopped then and looked into her slightly unfocused blue eyes and asked "are you ready?"

"Yes, oh yes." She replied.

Still looking deeply into her eyes I firmly pushed into her until my cock was full in her, I felt her tear. When I was fully inside her I stopped still so she could get used to the feel of a man inside her for the first time. I was surprised that I had had to break her as I thought Jan would have used a toy on her, but I wasn't complaining!

Jill seemed to nod as I began to push in and out of her pulling all the way out then back in fully in a slow and easy movement, I could feel her stretching and expanding as I pushed into her and then tightening on me as I pulled out. I'd never had a virgin before it was a wonderful feeling.

"God that feels so big, I can feel you filling me up." Gasped Jill.

"Just average size," I said "Jan has had bigger."

They both gasped at this so I said to Jan "you forgot I played football with Steve so I've seen the size he is and he was one of your longer time boyfriends."

I felt I needed so more action now so I increased the pace and strength of my pushing into Jill as she got used to what we were doing. I really began to slam deep into her I'd changed from making love to her to fucking her. I felt my own orgasm build and shouted "Jill I'm cumming, hold on to me clench me if you can."

I felt her try and clench her pussy on me as I exploded and shot the first of my hot cum deep into her welcoming pussy. Her eyes shot wide open as she felt my load hit deep into her.

"Ohhhh I like that." She cried and then she tensed up and came for the second time that night, her orgasm came from nowhere, I hadn't done anything, it must have simply been the feeling of me flooding her pussy with cum.

I felt myself soften inside her and slowly pulled my cock out of her feeling a dribble of cum follow me out and run down her ass crack. I lay beside Jill on the bed and kissed and caressed her as we both recovered, I was back in love making mode now.

Jan came over and kissed Jill asking "how was that, did you like it?"

"I liked most of it, it was different, my orgasm was not the same as with you, it came from a different place."

"Jan, you're not involved with this yet, Jill is still mine, she wanted a man, she's mine all night."

If looks could kill then I was dead from the look my sister gave me then.

"You've made love to her. What more is there to do?" she asked.

"I said I was going to have her mouth and her ass tonight so there's lots more to come. That's if Jill wants to, but it's her call not yours."

"Jan, I said I wanted him in every way and I meant it, I love you but I need John for tonight."

Jan jumped off the bed in a huff and left the bedroom slamming the door behind her. I looked at Jill and said to her, "what's next, we've got all night even if Jan's not happy. That's the agreement."

"I'm very nervous about anal, I don't want to do that, please don't ask me to do that. I know I said I would but I don't want to." Jill said she was nearly crying at the thought.

I wanted Jill to enjoy the night well I was keen to have sex with her again so I said "Whatever you want we will do, what you don't we won't. I won't force you."

"But you said you wanted me in every way!"

"I was testing you to see how committed you were, was it just an whim or did you really want sex with me. I want you to enjoy tonight, if you want to stop now I'm ok with that, I'll go and get Jan for you."

"NO. NO. I want to spend the night with you. Just make love with me again, lets do it harder like a quick fuck, and different positions, I'll even suck you off. That is something I've always fantasied about even before I thought about sex with a man."

We made love a couple of more times that night slow and lovingly, then I fucked her hard and fast, doggy position just before we fell asleep. I don't know where Jan slept, maybe she went to my flat.

When I woke up in the morning it was in the best way a man can wake up, my cock was hardening in a soft, warm, moist mouth. Jill was going down on me. She broke off from what she was doing smiled and said "Morning, this is for you, you don't have to lick me or touch me, just teach me what to do, don't stop I know what will happen, I want to taste your cum."

My sister was engaged to one very sexy and loving girl!

I looked at Jill and said, "Jill in my mind one of the sexist and loving things a woman can do for a man is to let him cum in her mouth, to my mind it is a total commitment of love, even more so if she swallows. Are you sure you want to do this; if so I'm just going to relax and lay back and let you take the lead; lay along side me and get your head in my lap and do what comes naturally."

"Just do what you were doing to wake me up, nice and soft and gentle, then when you are ready increase the pace or how deep you take me, it's all upto you, and stop when you want to."

"I'm going to do everything, I'm not stopping or pulling off, please relax and enjoy it." Said Jill.

Jill lay so that her head was in my lap and the rest of her body lay on my legs ,pinning me, then smiling at me bent her head, opened her mouth and wrapped her soft full lips round my throbbing and eager cock. All I could see as I looked down was her dark hair and head moving up and down on my cock.

At first she was hesitant, not sure what to do, just half taking me in her mouth, then she started to take me deeper for a while, she was ok but not great! I needed to give her some instructions, so I pulled her head off me and said, "Jill, just lick me, run your tongue round the head, then flick it, with your tongue, then take it as deep as you can."

Jill followed my instructions and her technique improved as she grew more experienced, she then started to tease me with her lips as she found out that running her tongue round my glans with her tongue between the head and my foreskin was something that drove me crazy, she'd do this for a minute, then break away and take me deep, then back to the tongue action.

The next time she took me into her mouth I pushed deep into her, just to the back of her throat, and held there, she gagged and pulled off. "What are you doing?" she asked.

"Just getting as deep into your beautiful, sexy mouth as I can." I replied, "That's not deep throating me yet you know."

"Do I have to, deep throat, I mean?" asked Jill with a look of worry on her face, "I'm not sure if I can do it it's so big."

"If you want to you will do, just relax your throat and let it happen, but I'm not pushing you into anything, I just want to cum in your mouth, just tease me to a finish."

Jill got her mouth round me again and built up a nice rhythm, getting deeper and deeper all the time, I was gently pushing my hips up so my cock was going deep into her warm soft mouth. Jill got me just to the back of her throat and I felt her try and relax and open her throat, I knew she was committed to try and deep throat me, so gently pushed my cock deeper into her mouth just broaching the entrance to her throat, then quickly pulled back out. Jill paused for a moment then pushed back down on me taking me all the way into her throat, such a nice feeling as her throat stretched and suctioned on my dick. This time Jill pulled off then wham she was hard at it deep throating me for all she was worth.

I knew I wouldn't last much longer and as I felt my orgasm build pulled back so Jill had me just in her mouth, moving slowly back and forth, then with a shout of "JILL, I'M CUMMMING." I shot a load of hot cum into her mouth, she gagged at first, but credit to her held on then started to swallow.

As I came I heard the bedroom door open and Jan walked in, she stopped, looking at me and Jan in shock, with wide eyes, then she came over to us on the bed and kissed Jill on the cheek and said, "Jill, that was one of the best sights I've ever had, you looked so good on John. I hope you two were happy last night."

"Yes, oh yes." Said Jill with cum dripping from her lips as she did so.

"Thanks sis." I answered.

"I'm sorry I stormed off last night, I was just jealous." Said Jan, but jealous of who I thought?

We spent the morning messing around the flat, had some lunch then the Jan threw me out with instructions not to come back until about seven as they had things to discuss. Intriguing!!

When I got back to the flat Jan answered the door, she looked stunning in a short red leather miniskirt and black bra top, four inch black heels, God this is my twin sister and she looked hot! Jill looked even better in a denim micro mini skirt that just covered her hips, pale blue blouse tied under her boobs and she obviously didn't have a bra on. The two skirts I love to see on sexy women are leather or denim and here they were on these two women. Jan knew this thing of mine so must have set it up.

What got to me even more is that Jan never seems to wear short skirts, it's a shame as she has great legs, all my mates used to tell me before she came out as gay, and this leather one was short, very short, not as short as Jills but short enough.

Nikkiejanes
Nikkiejanes
1,456 Followers
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