My Girlfriend’s Family

I am in an interesting situation. My college roommate is Luke. I date his sister Jamie. They are twins, but thankfully she’s the good looking one. I met Jamie through Luke and we really hit it off and over the course of my freshman year I also became close to their mom too. My home is about 200 miles from campus, but they are from about 30 miles from campus – really in the far suburbs on the opposite side of our rather large and sprawling metro area, so I have become a fixture at their house sort of.

Here’s how it began:

Since I was dating Jamie and roomies with Luke, I went home with them about the 4th weekend of the semester. We drug our laundry and went to camp in their house until Sunday evening when we would drive back all the way across town to school.

I met Luke and Jamie’s mom and she was awesome and really cool. Her name is Jane. Divorced, an attorney, they had a good life. And she was so fucking hot I was taken aback. Luke and Jaime look like her – obviously Jamie more than Luke, but Jamie and her mom are spitting images of each other really. They say if ya wanna know what a woman will look like in 15 years, look at her mom. Well, I did and fuck me rich! Jane was hot as Hell.

Jamie is about 5’5” and just the tiniest bit of baby fat hanging off her, but it looks so sexy on her. Unlike the anorexic look so many teenage girls thinks looks good, Jamie looks like a woman – nice tits, a waist, nice hips, round ass and my favorite – nice thick thighs, and calves – not fat at all, but womanly. And her mom, Jane? Holy fuck, is all I can say.

We walked into their nice fairly large transitional home on the outskirts of the suburbs and I was wowed! Jane met us at the door and I could hardly take my eyes off of her. She was the same height as Jaime, just a bit more of her – not too, too much, but perhaps an extra 20 lbs, and on the mature Jane it was all in the right places. She was certifiably “busty” with a great phat ass and hips, but it was her face and eyes that sent me into palpitations. She was sexy – she exuded sexuality, at least to me. When she would make eye contact with me I felt like a little kid. I hoped my being so enamored with her wasn’t too obvious. Me and Luke slept in his room and of course Jamie in hers, her mom in her master suite.

The first night passed normally – catching up and all that. Saturday we did laundry and Luke and I cut the grass and trimmed the yard up. Jamie and Jane went grocery shopping. In return for Luke and I doing such a bang up job on her yard Jane layed out a feast for us – roast beef, mashed potatoes and all the fixings, and damn that hot momma could, as an attorney, really put truth to the “bring home the bacon” and she could cook, so she could damn sure “fry it up in a pan” as it were. I was falling in love with their mom – or at least lust – my stomach and my innards were all way too excited, but I went with it.

We had a great meal and then their mom got high with us. She pulled out the liquor, Luke pulled out his stash of weed and we all got burnt and had a blast. We returned to school Sunday afternoon, full bellies and clean clothes.

The following weekend we stayed on campus for a football game, but the weekend after we hauled our asses and our laundry back to their mom’s house. She was so nice, there she was waiting for us and grabbing our laundry and helping out. Jane was too awesome for words. I was jealous of them having such an great and cool mom, and clearly one that made a great living and took great care of her kids. They both had new cars to boot, so I was jealous for sure.

Late that Friday evening we were partying again and getting wasted. Luke passed out about 11PM and Jamie soon followed. I was supposed to wait for her mom to crash and then sneak into her room and do the nasty again. We started screwing after our second date three weeks before and were fucking each other like bunnies now – every available moment we were naked and doing the deed, much to my pleasure and hers too, if I do say so myself.

It was 11:30 and I was waiting out Jane to get sleepy and go to bed, but we were the last two left from the friendly poker game, so we decided to play Gin Rummy. In the course of our second hand I could see Jane was kinda eyeballing me a bit on the sly. Then she began making very friendly remarks, asking me about dating Jamie, what was Luke like when he wasn’t around his mom and stuff like that. Then she started asking me about myself so we were chatting in a friendly way and playing Rummy. I noticed that Jane seemed to have unbuttoned the top two buttons of her blouse which had been buttoned to near the collar but was now open a fair ways down. Her cleavage was incredible. It rippled in waves when she laughed or moved a lot and I was enjoying the sight for sure, and I know she caught me peeking at her magnificent tit flesh. She would just smile and once she winked at me when she caught me eyeing her goodies. At that, my cock began to stir.

My seven and half inch pecker was fattening in my shorts, so I decided to see if Jane noticed. I got up and offered to get her another drink. As I stood it was clear Jane was checking out my crotch as she slumped in her chair. I made a big production out of tidying up where I was sitting and wiping up a water ring from my glass, all so she could look at my bulge if she wished, and she damn sure did too. I walked to her side of the table to get her glass to refresh it and decided to take another liberty to see if she bit.

I began to wipe up her water ring from her glass. I stood a bit behind her and could see way down into the magnificent cleavage. I lingered at my tidying up eying those tits. Jane leaned on me a bit and said “You are such a nice young man, Randy.” Then her elbow gently, almost “accidentally” rubbed against my bulging manhood straining at my shorts. Then she looked up at me and I was sneaking glances at her goodies and she said “Seems the view from up there is having some effect on ya Randy,” as she shot me a sly smile. I was embarrassed.

Jane smiled and said “Oh, don’t be embarrassed. Men look at these” she said, placing her hands under them and sort of hefting them a bit to make her point. “They are my ‘ice breakers’ sort of.” I was still embarrassed when she said “and it seems you have an ‘ice breaker’ of your own there,” as she blatantly looked at my bulging crotch. Then she looked up at me and the warmest smile crossed her face. Then she said “Well, the kids are passed out, so what shall we do to entertain ourselves now?” At that point I became a bit of an animal. I leered at her and replied “That’s a dangerous question to ask an 18 year old guy Jane, if ya know what I mean.” She smiled knowingly and shot back, “Yeah, I know.”

Jane, ever the clever attorney glanced at me with that look that said it all and added “Well, it’s too early for me to go to bed but I am losing this game of Rummy, so….” I waited for a second to see where she was going with this. In the back of my mind there was always the chance she was just speaking extemporaneously and being high and half drunk, maybe just a bit too friendly and flirtatious, so I remained cautious. Jane was having none of it though, to my delight.

“Let me help ya,” she said and she rose. She got a bit tipsy as she did and reached out and grabbed my shoulder. I reached and naturally in so doing brushed her tits, innocently, of course. She looked up at me and smiled. “They are always getting in the way, aren’t they?” she joked. I looked sheepishly at her and said “Oh, sorry Jane. I didn’t mean to….” I was saying when she looked at me and leaned in close to me smashing her abundant orbs against me and said “accident? Oh, what a shame. I was getting a thrill there for a sec….” and the look on her face was open, inviting and somewhat serious.

I grabbed her tits this time like I meant it and said “Ya like this a little better Jane?” She leaned her head back and closed her eyes and whispered “Oh God yeah!” I pulled her to me and we started kissing and I mean to tell ya, it was incredible. She let her hand rush to my crotch and then broke our kiss and whispered in my ear as she rubbed my crotch “But I like this a whole lot better.” Standing in her kitchen she opened my fly and put her hand in my pants. I wasn’t wearing underwear. She pulled on my cock and began to coo “Jesus Randy!” She tugged gently at my cock and looked back up into my eyes. “I know this is wrong, but ah….” I put my finger to her lips to silence her and said “It’s only wrong if we get caught.” She liked that and nodded. “Well, let’s not get caught then.”

Before I knew it we were on our way to the basement of her sprawling home. It was a rec room down there for Luke and Jaime when they were still living at home. It had two couches and a couple of chairs, a small college sized fridge and TV too, as well as a pool table. Jane pulled me by my hands to the pool table. She turned and leaned back against the bumpers of the table and took my hands and put one on each of those massive mounds and smiled up at me. “Ever been with a mature woman?” she asked. I replied with “Ever been with an 18 year old guy?” She was the first to end the Mexican standoff with “Not since I was 18 myself. So, now your turn to answer the question.”

“Yes” I confessed. “I used to sleep with a woman I worked for in high school. She owned a framing store, ya know, where folks brought their pictures and stuff to be custom framed? I worked for her and one lonely and quiet evening we ended up in the back of the shop after closing and well, ya know….” I left it hanging. She wasn’t having any of that though. “No, I don’t know. Tell me about it. Besides” she said as she planted little kisses on my face and neck, “It makes me hot to hear about you doing that with a mature woman.” I smiled and asked, You really wanna hear this now?” she smiled and said “Yeah. Makes me hotter! Let’s sex each other up some first.” I was okay with that.

“Okay Jane, I’ll spill the beans, but first if I am to answer your query, you need to answer mine. I guess I should ask ‘ever been with a much younger man, instead of an 18 year old.’” She smiled at me. “You’d make a good lawyer Randy. Go to law school and I’ll hire ya. Can I pay in pussy?” We laughed and she answered my question. “Nope, never been with a man more than a year or two younger than me. I don’t do this….” She sheepishly added. I feared she’d get self conscious and scared, but she wanted to hear it so I spoiled the beans. I told her about the “Divorcee Spencer” as I called my former boss and sex partner. I told her how I first noticed my attraction to matronly women as I hung around the sexy 51 year old Eileen Spencer. Eileen was the epitome of the “wife in the kitchen, lady in the drawing room and absolute whore in bed.” “Oh, so you like that whole prim and proper appearances thing, closely followed by nasty sex, huh?” I rolled my eyes and nodded. “Oh Hell yeah I do. Talk about making ya hot. Nothing like a woman who is all prim and proper to the world but behind closed doors she’s a tiger” I adamantly said. She seemed to enjoy that thought.

As I talked she began to slowly disrobe. If I stopped and started to pay too much attention to her actions she would remind me she wanted to hear all the dirty details. Seems Jane is an aural voyeur, kinda like me. I love sex talk, especially during sex, and as I would come to learn, Jane was all about that too, and really had one filthy little mind in that smart brain inside that gorgeous head of hers.

I continued to detail how Eileen came on to me. How she and I became close and I became her confidant sort of. How at 16 Eileen told me she was lonely but didn’t trust men due to her bad experiences in her past. She refused to go to bars to meet guys and didn’t want the hassle, that she was no longer a svelte young thing and men didn’t chase her all that much, but that she was a woman and she was like all women – she had a physical need for affection. And that became my primary job. We became lovers. We fucked almost every day when the shop closed at 6PM. My folks just thought I was a dedicated employee, and I was sort of – dedicated to having sex with Eileen Spencer.

How I was getting hot and jerking off fantasizing about my boss and how my boss never missed an opportunity to flirt or have a bunch of innocent body contact with me. I decided to put it to the test. As Eileen was a matronly woman, I put a plan into action. I bought a copy of a men’s magazine called “Plumpers” and left it in my open book bag that I left unzipped and sitting on the floor in the back of the shop at the little table we sat at and ate lunch and whatever. As I’d hoped, Eileen noticed the mag, and said something.

We were sitting at the table after closing one evening and I was helping her enter the checks onto a deposit slip to take to the bank. She saw the mag, her eyes perked up and she said “I see my employee likes women, and apparently likes the ‘plumpers’ huh?” I put on my embarrassed, “aw shucks” act and Eileen assured me that was okay and gave her hope that men liked matronly figured women. I launched into my enthusiasm for such creatures and in about 15 minutes Eileen was on the table and I was plowing her for all my young ass was worth.

Jane got excited as I told he the story and she began to tug at my clasp holding my pants up. She still had her hand in my shorts pulling on my cock the whole time I talked. She loosened the clasp and pulled down my shorts. “Oh wow!” was all she said as she looked at my cock. She looked back up to me and said “Fuck me and keep telling me about you and Eileen.” I slipped her out of her blouse as she slid her jeans down. I reached behind her with one hand and unclasped her bra. She admired my dexterity as I one-handedly slipped her out of it and her awesome tits fell free. I stopped talking long enough to lean down and suckle each nipple, lifting each pretty udder to my lips. “Ewww,” Jane spat at me, “You can talk filthy and use those lips for other things too! I like that!” she said.

She sat on the bumper of the table, I slid my arms under each of the backs of her knees and leaned my hips to her. She took one hand and guided me into her. She watched as I pierced her hole, then she looked up at me and pulled me by my ass all the way onto her. We began to kiss passionately as I pumped slowly in and out of her wet pussy. She held onto me around my neck, pulled herself all the way to me and whispered in my ear “Did Eileen like it when you fucked her?” I pumped Jane’s pussy more deliberately and replied “I guess so. She fucked me nearly every day until I left for college.”

That seemed to send Jane over the top. “Oh God!” she squealed. “Are you still having sex with her?” I lied and said no, not since before I left for school, which was a lie. Eileen came and took me to dinner on Tuesday of last week and we fucked until 4AM when she took me back to my dorm, so….

Hearing the sex tales made Jane so fucking hot she became a wild woman. She was kissing me, her tongue all over me. She kissed every part of my naked body she could get to as I fucked her on the pool table’s bumper. She came three or four times and began to encourage me to “fill me Baby.” I pumped for all I was worth and as I began to dump a massive load in her she came again and held me so tight I could hardly get a breath.

As we recovered she seemed ready for more and I know I was. She slid of the table and knelt at my feet and began to suck my half hard cock back to full hardness. I put my hands on her head and she loved that. She put her hands on top of mine and began to push my hands to push her down onto my cock. I took over and face fucked her and she loved it. She once looked up into my eyes and winked at me as I fucked her face. I had to kiss her again so I pulled her up and told her that her mouth was awesome but I wanted to look into her gorgeous eyes and “make love” to her. She led me to one of the couches and lay on it and pulled me down onto her. The passion was incredible for sure. We made love and both came again. I laid on her as my pleasure passed and we made plans to pick up in the morning where we left off.

We snuck back upstairs and retired to our respective sleeping quarters. In the morning I awoke to Jane standing over me. She’d sent Luke and Jaime to get us breakfast and Jane wanted a quickie before they returned. As usual morning wood was exploding and before she would let me piss she squatted onto my hardon, opened her robe and slapped my face with her tits. I bucked and held her to me as we both came again. She jumped off me and made it back to the living room just in time for Luke and Jaime to return. I let my woody subside and went out. Jane said “Well, sleepy head gets up.” Jaime came to me and gave me a peck and said good morning to me.

I sat and ate nervously, but Jane was way cool. She shot me a few knowing glances but other than that no clue whatsoever. We never had more than a couple minutes alone the rest of the weekend and on Sunday we returned to school. Jane managed to get my cell number and told me she’d call and make some private arrangements.

Monday at about 1:30 my phone rang. “Hi, it’s me Randy. Are you alone? If not play it off as a wrong number and I’ll know Luke or Jaime is around.” “No, it’s cool Jane. Luke has class until about 4PM and Jamie is studying in the library, so I am free to talk. Is everything okay?” I asked. She breathed a sigh of relief and sort of moaned, “I missed you and wanted to hear your voice is all.” We chatted briefly. She wanted to know why I wasn’t in class and I informed her I take all my classes in mornings so my afternoons and evenings are mine. I told her I have no class after 2PM any day of the week. She then asked “So, are you busy now? Any plans this afternoon?” I replied nope, just sitting here watching TV, studying some and getting ready to go to the dining hall for some lunch. She replied “I am in my car outside your dorm. Come on down and I’ll take you to lunch. Would you like that Randy?” I replied “sure” and hung up and headed down to meet her. I ran out the door and found her car off in the lot and jumped in. We pulled off campus and Jane turned onto the highway away from school.

We made small talk, “How was class, blah, blah, blah” and Jane turned off on the third exit and pulled into a hotel‘s parking lot. She ran in, got a room and said “c’mon and let me put some food in ya. You’re going to need your energy.” We ran to a Subway, I ran in and got a 12 inch Tuna sub and we hauled back to the hotel and carried the food in with us. I have never eaten and fucked at the same time, but apparently I am talented enough to pull it off, cause I ate some, made out with Jane, ate some more, got a blow job, ate some more and then when I finished my half of the sub she fucked me stupid.

She climbed on me and did all the work. I played with her tits the entire time and we took our time too. I asked her why she wasn’t working today and she told me she didn’t have court this week and as the boss at the law firm she owned she delegated. She had no client appointments so she turned her two paralegals and legal secretaries onto research, typing legal mumbo jumbo and all that. We fucked and talked all the while. I liked this. She was vocal as Hell and so was I so we fed into each other’s little passions.

It was 4 o’clock before we knew it and she drove me back to school and dropped me off on the other side of campus so we would not be seen. We also agreed beforehand that if seen together we would claim innocence and just say she called to take Luke or Jaime to lunch but I was the only one around and as a family friend and hungry college student, she fed me. Innocent, right? We parted and she was adamant that our coupling was getting real good to her.

Part II will follow . . . .

---