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My Girlfriend’s Best Friend – Part 2

4739 words | 2 |4.22

The night continues…

Ruth was still holding my cock and it hadn’t softened at all. I was breathing hard as I looked down. Her expression was either one of shock or one of horror. Perhaps I shouldn’t have cum on her face.

“Is…is that… normal?” she asked with surprise in her voice.

“Oh shit, Ruth, I’m so sorry!” I tried to apologize and explain. “No, that’s not normal for me. I didn’t mean to cum all over you. But I was so turned on by your stories and I couldn’t help myself. I usually last a lot longer…”

Ruth stopped me with a shake of her head and a quick giggle. “Oh, jeez, don’t worry about that. I’ve seen my mom covered in a man’s semen enough times that I kind of expected it to happen. No, what I’m asking about is, there’s just so fucking much of it! I’ve seen a few cocks shoot their load, but nothing like this! Seriously, do you ejaculate this much all the time?”

Ejaculate? Who the fuck talks like that? Especially a teenager! I nearly laughed.

Plus, that’s one of those ‘unreal’ questions, right? I mean, how do you answer? I never really paid attention to the volume of cum my body produced, much less compared it to anyone elses. And I rarely masturbated since I had so many willing participants that engaged in sexual activities with me, so I wasn’t really versed in what was a normal amount of ‘ejaculate’ for me. I never had any previous complaints, though, so I just shrugged.

“I dunno”, I answered honestly. “Seems about the same as always.” Ginny let me do whatever I wanted and sometimes I blew all over her like I had just done with Ruth. Looked about the same to me.

Ruth kept shaking her head as she reached for a box of tissues on her night stand. She finally let go of my rigid cock and it sprang up, the head bouncing a couple of times against my belly because of it’s curve.

“By the way, you have what my mom would say is a very pretty penis. She says that the ones that curve up and back to a man’s belly like yours does are the best to hit a woman’s g-spot. Not quite sure what that means yet, but I hope to find out in a little while.” She finished wiping my cum off her face then focused her attention on me again. “Wow. If that’s, like, normal for you… I dunno, Rocky. Maybe we should show my mom how much you ejaculate and ask her about it. She’s seen a ton of penises do their thing. If anyone would know, it would be her.”

I pulled back in surprise. “You really want me to cum in front of your mom?” Fucking unbelievable!

Ruth bit her bottom lip and eyed me up and down for a few seconds. Then she smiled and shook her head.

“Nah. She’d probably grab your pretty penis and steal you from me. She had me when she was fifteen, so she’s only 31, and everyone says she’s really hot. She is beautiful and you’d go for her without thinking twice about it. Maybe we’ll just keep this to ourselves”, she finished as she leaned in and grabbed my dick again.

As she began stroking it once more, all I could do was agree with her. Of course, in the back of my mind I was filing away the information about Ruth’s hot mom for later consideration. I had zero qualms about fucking an older married woman, even if it was the mother of my ‘girlfriends’ best friend!

I laid down on the bed with Ruth and began giving her my undivided attention. Now that my first cum was out of the way, I would be able to concentrate a bit more on the task at hand. And that task was to invade Ruth’s virgin valley with as much pleasure as I could provide for both of us. Luckily, I had a great arsenal to back me up and I got down to business.

From everything Ruth had told me, it sure seemed as if she wasn’t quite as innocent as the other first timers I had been with. So I opened up my mental playbook and skipped past the first few chapters for beginners and delved into the intermediate area.

She had no problem putting her lips around my dick, so she wasn’t afraid of it. She had stroked me masterfully, so she knew how to handle it. She wasn’t afraid of getting messy, that was for sure. And the way she readily spread her thighs apart for my hand definitely proved she was willing to go all the way.

So I had to ask myself two questions. Was this chick REALLY a virgin? And if not, did I care? Answer to question #1: didn’t matter one little bit. Answer to question #2: abso-fucking-lutely not! Ruth was new pussy for me, and I loved, loved new pussy!

We did the making out/foreplay thing for a while, and Ruth allowed my hands full access to every part of her body. She didn’t even blink after I got her really wet by fingering her cunt, then traced some of her juice down to her asshole and played there for a bit. Well, she might have blinked but I was paying attention to other stuff so I wouldn’t have seen it anyway.

I had to get a taste of Ruth. I got between her thighs and took in her pleasant aroma then let my tongue slip into her wettest place, committing her scent and taste to memory.

She tasted ‘right’ to me. Not as sweet as Jocelyn, but then it would take me years to find another snatch that was equal to my true blonde’s puss. But Ruth tasted very good; untainted is the word that comes to mind. And I devoured her with gusto.

It wasn’t long before I was rewarded with a number of low moans. They built into a long, soul satisfying groan that ended with a series of quick breaths, several grunts, her hand reaching behind my head and grabbing my pony tail to pull my face harder against her mound, and one final high pitched wail that sounded more like a Halloween witch’s scream than a pleasurable orgasm.

I gave her a few moments to recover while I placed soft kisses around her well tended garden. When she regained some of her composure, she lifted my head up by my pony tail and spoke in a husky whisper.

“That felt amazing! Can you do it again?”

My lips were attached to her pretty little clitty, so I mumbled an ‘mmm-hmmm’ and the vibration from my mouth must have set her off again. The effluvium seeped from her vagina as she moaned, and I lapped it up like the dog I was. Like I said, she tasted right.

When I heard that witch’s wail once again, I knew it was time to give her what she really needed. I slowly climbed her body, kissing my way up, pausing at her breasts to nip at her beautiful nipples. She trembled each time my teeth grazed along them, and before Ruth realized what was happening, my cock was pushing against the entrance to her virgin valley.

By the time she recognized the implications of where my throbbing thickness lay, my face was hovering over hers. Ruth’s eyes popped open as I held my pounding penis at the threshold of her promised land. I kissed her, letting her taste herself from my lips.

“Ohhhh”, she moaned into my mouth as my tongue found hers for a quick dance. I pushed past her labia and met resistance at the beginning of her tunnel of lust. I wanted to thrust deep inside but knew it was the wrong thing to do, so I eased my stiff cock back then gently pushed past the resistance until the broad head and first couple of inches lay within her.

Ruth gave a little gasp and clinched a fist against my chest. I knew she just needed a few moments without movement so the pain could subside before continuing. When I felt her body relax underneath mine, I drew back then pushed my thick prick in half way. This was usually the spot where most women began having their cunts stretched beyond their comfort level, and I knew Ruth would be no different. And I was right.

Her face contorted, her body convulsed, and she cried out, “OH, FUCK!!!” She blinked rapidly a few times then stared into my eyes. I recognized the fright within them because I had seen it before.

“Ruth, I won’t move again until you’re ready”, I whispered. Her face still told me that she was scared. I can’t say I understood at that point in my life, but a time would come about four years later when I would understand all too well. A large foreign object invading a place in your body that has never before accommodated such a thing isn’t easy to overcome.

I spoke in whispers, calming her, letting her know how beautiful and desirable she was. It took several minutes but I saw and felt the signs of relaxation and asked if she was ready for more. She nodded her assent and kissed me deeply. I pulled my cock out a couple of inches then slowly pushed in, only millimeters at a time, out and in, repeating the motion an untold number of times until I sank all the way, her fresh pussy stretched to capacity as I rested my pubic bone against hers.

“Oh…migod”, she whispered hoarsely. “I can’t believe that whole thing is inside me! I didn’t think it would really fit. God, I feel so full.”

I had to smile at her. “I promised you it would fit. How are you doing? Does it still hurt?”

She paused to evaluate herself for a minute. “Mmm… I wouldn’t say it was pain, really. More like discomfort, very stretched out. You’re not gonna fuck me really hard, are you? I’m not sure if I’m ready for that kind of sex yet.”

“No, Ruth. We’ll take it slow and easy. I won’t get ahead of you. We’ll both know when it’s time to get after it. For now, we’re just going to ‘make love’, not fuck, okay?”

I could see the relief on her face. “Okay. Thanks. You know, you’re not as much of a jerk as I was expecting. You hear so many stories, ya know, from other girls and you don’t know what to believe. I’m very glad that you’re taking it slow, though. I don’t know how I could’ve handled your cock if you’d just shoved it in me.”

I could only shake my head. I know I was a dog. I was never faithful to any one girl until I met the woman I would marry several years later, but I never purposely hurt anyone during sex either. I was always careful with the high school girls, making sure that I didn’t just shove it in before knowing if they could handle it. I think at least some of my bad reputation came from girls who got jealous or mad because I didn’t choose them as my one and only. Oh, well. Just added to the mystery that was me.

Ruth handled herself extremely well during our first fuck. We did go slow…at least for the first ten minutes or so. But once she began feeling the pleasures that sex could bring, she became more aggressive, which made me more aggressive.

By the time I was reaching the point of no return, I had her crying out with her very first penile produced orgasm, no small feat with a sixteen year old virgin. I believe a lot of that is mental, being prepared and understanding your own body. And I believe that Ruth’s mom helped her daughter to be very prepared for this moment.

After she finished the downslide from her cum, she opened her eyes as I held my throbbing thunderstick deep within her and asked me, “You’re not going to ejaculate inside of me, are you? You don’t want me to get pregnant, do you?”

I lost it. I’m not sure what happened in my brain when she said that, but at that moment, I DID want to get her pregnant. I wanted to fuck her pussy so god damned hard and I wanted to flood her vagina with my cum. And yes, I wanted to get that girl pregnant!

I remember reaching underneath her and grabbing her ass with both hands, pulling her pussy off the bed and just pounding Ruth with everything I had until my dick exploded. I was so excited that I forgot about it being her first time and that I wasn’t supposed to get ahead of her. But that biological imperative to procreate had taken over and I couldn’t think straight until after my rigid rocket had dumped all of its fuel into Ruth’s awaiting vessel.

Only as I was laying on top of her, my lust finally sated, did it dawn on me what I had just done. I quickly pulled my softening joy stick from Ruth’s tender patch and began apologizing profusely.

“Oh, holy shit! Ruth, I’m so fuckin’ sorry! I… I didn’t mean… I wasn’t trying to… I…”

Ruth was laughing! She was laying on the bed laughing at me! WTF???

“Oh…migod! That’s just too funny!” Ruth had to hold her belly as she laughed even harder. “Your face! Oh…migod! The look on your face… priceless! Did you really think that MY mom would send me out into the world without being prepared? She got me on birth control pills after she heard about a girl in my junior high class getting pregnant, and I was only thirteen!” She laughed even harder.

She was on birth control? I sat back on my heels with my hands on my hips. Didn’t she realize that she had just ruined the afterglow cuddling moment? The post-coitus elation of a good fuck just gone with a giggle. She was on fucking birth control? Shit and god damn. I was speechless for one of the few times in my young life.

Ruth finally stopped giggling and pulled me down to her. I was a little bummed but had to laugh at myself. I mean, what else was I gonna do?

“Oh, c’mere and give me a kiss”, Ruth slyly said. “And thank you. For a first time, I think we did pretty damn good. I know you rocked my world like it’s never been rocked before! I have to say, the girls weren’t lying about you. You do seem to have a magic dick. How was my performance?”

??? Once more, I was surprised by this girl. No other had ever asked me about their ‘performance’. What could I say?

“Well, Ruth, for a first time you did… really fuckin’ fantastic! You have a pretty sweet pussy, too. And once I was all the way inside of you, it felt amazing. But the thing that makes you stand out from the rest is when you asked if I wanted to get you pregnant. That turned my brain into mush and all I wanted to do after hearing that was to try my damnedest to get you pregnant. The primitive part took over and I lost control. That was fuckin’ hot!”

“Wow. I’m glad I could help out. And I felt it. The, the losing control part? Oh… migod! When you grabbed me and took me, took what you wanted, that made me… I felt… that was so hot! I couldn’t believe the orgasms I had! Thanks for…well, you know.”

We laid beside each other spooning with my semi-hard cock pressed against her ass crack. I lifted the top cheek and let the bow of my prick settle against her tight little anus, then reached around her belly and pulled her closer. I kissed the back of her neck and shoulders, running my hands the length of her body, caressing her soft sexy skin. She shuddered and giggled repeatedly as my fingers explored every part of her that I could reach.

“I’m not sure if I’ll be able to actually fall asleep”, she confessed, “since I’ve never slept with a guy before. It feels weird… good, but weird.”

“I doubt that we’re gonna do much sleeping tonight, Ruth”, I told her. I wanted her to know the truth. “We’re probably gonna have a lot more sex by the time morning rolls around.”

My cock had already begun to revive. And since it was lodged between her sweet little ass cheeks, she felt it too.

“Holy shit!” she exclaimed with surprise. “Are you kidding me? You’re ready to go again?”

I just pulled her against my chest and held her there. “Mmm… let’s lay here a few minutes till it gets nice and ready for you. Feels pretty good right where it’s at.”

It didn’t take long before she was turning towards me and we were tongue to tongue again. By the time my cock was pulsing against her belly, Ruth was ready to be mounted. She laid back and greedily pulled me on top of her. There was no fear in her eyes this time, however. All I could see was pure unadulterated lust. She was ready to be fucked.

We were in the midst of the throes of passion so we missed the sounds of her parents coming in the house. Both of us jumped when we heard a high pitched squeal emanating from the archway that led into her bedroom. It wasn’t really a scream; it sounded more like a tea kettle. I looked over my shoulder and saw the outline of a person standing in the doorway.

“Oh…migod!” was the next thing I heard. “Gregory! Come see! Our baby girl is having her first sleep over with a boy!”

I figured this had to be Ruth’s mom. I understood then where Ruth got her ‘Oh…migod’ thing from, making ‘my god’ sound like one word. A light flipped on overhead and I had to squint for a minute.

“Hi, mom”, Ruth said in a resigned voice.

Ruth’s mom shuffled a few steps into the room and squealed again. I almost laughed because it seemed absurd to me that a mother would get so excited about her sixteen year old daughter having a boy in her bed. There was no fucking way my mom would have been cool if she had ever caught me with a girl in my bed under her roof.

“Oh… migod! I’m so excited for you, honey!” Then she took a good look at me as I rolled off of her daughter. “And look, Gregory! An older man! Ruthie, you’re so much like me. Oh… migod! Look at this young man, darling. He is absolutely gorgeous! Look at his muscles. Oh, Ruth, you really picked a good one, didn’t you?”

“Rocky, this is my mom, Maria. Mom, this is Rocky”, Ruth said in introduction. “And he’s not really an older man, mom. He’s only seventeen, a year ahead of me in school.”

Maria looked surprised. “I would have thought you were much older. You have a beard… and those muscles! My goodness, you have some big ones, don’t you? Darrell, look at this young man. He’s built better than you are.”

That’s when I noticed two more figures standing in the archway. One was a gentleman who appeared to be a lot older than Maria. He wasn’t very tall, was bald on the top of his head but had short hair around the sides, was wearing nerd type black rimmed glasses, and looked to be about as thin as a pencil. He wore a soft smile on his face and seemed unaffected by it all.

The other guy looked like he was about mid-twenties. He was clean shaven and I guess what girls would call good looking. He looked embarrassed by what Maria had just said. His frown pretty much said he wasn’t very amused.

Maria was running her hands over my chest and arms. Ruth introduced me to her dad, Greg, and Darrell, who she called her mom’s boyfriend. Greg politely nodded at me while Darrell shoved his hands in his front trouser pockets and looked on sullenly. I thought the guy was a real prick. Seemed like the kind of guy whose ass I would kick if he ever got in my way. Fuckin’ asshole was my initial assessment.

“Oh my, Ruthie! I can’t wait until we can talk, my sweet daughter!” Maria was blowing my mind with how cool she was with the situation. My mom would’ve killed me by this point. “We’ll have to compare notes in the morning.”

“Dear?” Greg said to gain her attention. “Why don’t we let Ruth and her young man get back to what they were in the middle of. We certainly have our own needs to satisfy, don’t we, darling?”

Maria looked disappointed, like she wanted to be present during what would be Ruth’s second fuck. “Oh, I suppose you’re right, Gregory. I do have Darrell’s little cock to take care of tonight.”

Both Greg and Darrell blushed bright red after she said that. I almost busted out laughing because I couldn’t think of a single good reason why she would say that unless it was true. Ruth had said her dad wasn’t well endowed, but I thought she had mentioned seeing a long cock from one of the stories about her parents activities

When the adults had cleared the room, I asked about it. “What was that about Darrell’s little cock? I know you said your dad had a pretty small one, but I thought you said he had a pretty long one.”

Ruth shook her head. “I’ve never seen Darrell’s. That was a different guy I saw with them. Darrell’s only been around for a couple of months. Before him, her regular guy was Davis. He had a long one. I doubt it was as big around as yours, but it was definitely longer. Not that anyone would call you shorty. God, believe me when I say you’re plenty long… and almost too big around! But I’m ready to get back to it if you are.”

She didn’t have to offer twice. My cock was still rigid, especially after seeing Ruth’s hot mom, Maria. She had been wearing a skin tight white dress with no bra. How did I know that? Because the dark areolas of her breasts showed through the material, as well as her erect nipples. Maria’s ass looked to be perfectly formed as well, from what I could see. If Ruth grew into a hottie like her mom? Fuck!!!

Our second round lasted much longer and I didn’t shoot my load until I knew Ruth was spent. By the time I was ready to cum, my cock was screaming for relief, and it came when Ruth accepted my deposit into her treasure vault. It wasn’t nearly as powerful as my last cum when she talked about getting pregnant, but whenever I got to cum in a sixteen year old pussy it was always good.

As we were laying together I could hear noises from elsewhere in the house. I asked Ruth if we could climb the stairs and check out what was happening in her parents room. She didn’t seem real interested but after a couple of more ‘c’mons’, she acquiesced and put her robe on. I chose to remain in my birthday suit because I was really hoping that Maria would catch us and kick Darrell to the curb in favor of me.

We did a pretty good job of staying quiet as we snuck up to where we could see into her parents bedroom. I held Ruth in front of me as we watched the proceedings. Ruth’s dad was laying on the bed on his back with his head at the bottom of the bed licking his wife’s pussy. Maria was kind of in a 69 position above him but wasn’t sucking his little dick although his three incher was sticking straight up. Darrell stood at the foot of the bed behind Maria’s ass and was trying to fuck her doggie style. But he kept slipping out and his less than fully erect prick kept slapping Greg in the face.

After about five minutes of that, Maria slid off her husband’s face and sat on the bed. She stared at Darrell with a look of concern. Darrell just stood there with his eyes downcast and his hands on his hips. I could also see that his penis was pretty much hanging limp.

“Darrell, baby, what’s wrong?” Maria asked in a motherly tone. “This hasn’t happened before. Is it me? Am I not turning you on anymore?”

What the FUCK??? God damn! If Darrell wasn’t hot for Ruth’s mom… I couldn’t even imagine having the opportunity to put my cock in that woman and not be able to do it! Shit, if that had been me up there I would have been ramming that cunt full speed ahead!

Darrell shook his head and took a couple of breaths. He said something that neither Ruth or I could hear. Maria must not have heard it either because she asked him what he had said.

Darrell muttered louder, “Do you really think your daughter’s little boyfriend has a better body than mine?”

He sounded like a fucking crybaby! Like I said, my first assessment of the dude was ‘fuckin’ asshole’. Boo fuckin’ hoo! I had a better body than 99% of the population of Salinas! Quitcher bitchin’, dick face! You’re getting to fuck one of the hottest wives in town! What the hell did he have to complain about?

Apparently, Maria agreed with me as she pouted her pretty lips and said, “Oh, did my little boy’s feelings get hurt?”

And just like the little bitch he was, Darrell got pissed, picked his clothes up from the floor and started getting dressed. Me and Ruth took that as our cue to head back to her room.

But before we were halfway down the stairs, I heard Maria laugh and say, ” Oh… migod! You really ARE mad at me for saying that! Darrell, I wouldn’t have guessed you were such a pussy. Jesus!”

The rest of what was said isn’t important. Just know that Maria cut that prick down to size every time he tried to come back with something. After the dick had stormed out and slammed the front door behind him, I heard Ruth’s dad, Greg, say something like, “He picked the wrong woman to argue with!”

I couldn’t hear what Maria said, but I did hear some kissing and moaning until the sounds faded as Ruth’s parents returned to their bedroom.

Ruth and I were back in her bed by that time and I couldn’t help but have a serious erection. It wasn’t because Ruth’s mom was seriously hot, though. Well, some of it was. But mostly I was hard because of the way she cut that mother fucker down! That’s what was so hot.

Plus, Ruth was holding my dick again. I guess it had got her pretty hot, too. She took me in her mouth and, although she didn’t give me a full blowie, she got me to the point of nearly popping my cork before sitting on me and riding me until she had an orgasm. I’m sure that she made me cum somewhere along the way, but whether it was before, during or after her own cum, I can’t be sure. I just know that my penis was extremely happy by the time the two of us finally fell asleep in the wee hours of that morning.

I never did get to fuck Maria. And I totally regret not taking the initiative to do so. She was a super hottie. But I got to keep fucking Ruth pretty much whenever I wanted. There’s more to the story, so keep watching for ‘My Girlfriends Best Friend part 3.

Thanks again,
Rocky J.

P.S – girls, do you ever leave your guy alone with your best friend?

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  • Reply XXX m ID:14s628gyxid

    Rachmael is hands down an OG on this site and in mind wont be forgotten. See ya round Rocky.

  • Reply Mark ID:fx7itagqj

    Great stories…. I had a 5 year affair with my ex’s best friend. My stories chronicle that.