Fiancé, Lovers, and Creampie Pt. 02

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Randy shares sexual history with new girlfriend.
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Part 2 of the 2 part series

Updated 06/10/2023
Created 04/17/2021
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NerdySex
NerdySex
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"Want to have a beer before we go?" Jenny asked as I came to pick her up for our date.

"Sounds good. You having one too?"

"Sure. I'm too young to go to a bar. Where are you taking me?"

"I thought we could go to Murphy's for dinner and then catch a movie. That sound ok?"

"You bet. I'm mostly a homebody, studying when I wasn't in school or working. So it will be nice to get out. Nancy says you also went to UC. What was your major?"

We continued to make small conversation and almost an hour went by before we noticed. It was too late for a movie but just fine for dinner. Jenny was a classy girl and turned every head when we got to the restaurant. I felt proud to have her on my arm.

I asked about her acting career. Her father had connections in the business and helped get her started when she was twelve. She has been working part-time but consistently ever since.

"It's a tough business, Randy. I'm nineteen and figure I have three, maybe four years left if I'm lucky. So school is really important to me. My mom is a doctor and dad is, as I said, in the business. He's on the financial side of things. That's what I would like to do after I graduate, get into business. In the meantime, the acting is fun and pays well."

Dinner was awesome. I don't know what I ate but it was the best dinner ever. Jenny and I just clicked. I'm four years older but she seemed so mature. We kissed as I dropped her off, having made a date for two days away. We made it to the movie that night.

It was our third date and I wondered if I should make some sort of move. I sensed an undercurrent of pent-up sexuality but she seemed so proper that I hesitated.

"You are going to think me just awful. Let's skip the movie and go back to your place. You don't mind, do you?" she said with a gleam in her eye.

"Guys are supposed to make a move on the third date, isn't that right?" She said as we opened the door. "But why does it always have to be the guy? Girls get horny too."

She stood before me and slowly undressed to her bra and panties. 5 foot 9 inches of loveliness. Slender model figure, super long legs. B cups as she unclasped her bra.

Come here, pull down my panties." I knelt in front of this goddess and stared at her beautiful bare pussy.

"You like, huh? Now your turn. Nancy says you've got a big, beautiful cock. Show it to me."

This young girl was in total control and I was like a puppy. I quickly shed my clothes and watched her face as my cock popped out. I was pleased with the subtle bite of her lip. Good, she was impressed. I took her close and hugged, my hands on her ass and my cock smashed between our bodies. We kissed, and kissed some more.

She sank to her knees and took my cock into her mouth. This beautiful girl was sucking my cock! Unbelievable. I was determined when it was my turn to make sure she was fully satisfied.

She took almost all of my 8 inches and sucked me dry. It was obviously not her first time. Interesting. We moved to my bed. I kissed behind her ears, then down her neck, her nipples were like hard erasers as I gently nibbled. I continued downward, fucking her belly button with my tongue. As I approached her crotch she spread her legs wide, giving me access. Her delicate pussy lips were already seeping pussy juice. I nudged them apart with my tongue and licked up and down.

She played with my hair as I mouthed her vagina, using my tongue as a cock.

"I like that, Randy. Feels so good. I won't last too long."

I was rapidly finger fucking and licking her clit when she climaxed.

"You ready for my cock?"

"Do me doggy, that's my favorite. But go slowly, I've never had one as big as yours."

Words any guy would like to hear. I rubbed the head up and down between her lips. Then positioning at her vagina I gently pushed, my cock head entering her hole. Very snug. I pulled back out and again rubbed up and down between her lips, and then back to her hole. Two more times and then stayed in position.

I sensed that she wanted more and pushed in another inch. Back out, then in. I had already come once so was patient, this was for her. Each time I went just a bit deeper, her opening snapping shut as I withdrew. Now I was half way inside, her pussy gripped my cock.

"Doing ok?"

"God, yes, feels so good. I'm ready, fuck me hard."

I held her hips and thrust deep. One more thrust and my balls bumped her crotch. I fucked her hard and deep.

"What are you doing, Jenny? That feels incredible."

She was using her pussy muscles to milk my cock, gripping the shaft in waves. I had never felt anything like it.

"Better stop or I'm going to come."

She continued and moments later I pumped deep into her pussy.

"You didn't come?" I was very disappointed.

"Not yet. I was trying to hold back. I want you to eat me. Nancy said you do creampie."

Her pussy was red and engorged, some of my cum between her lips. I quickly pushed my tongue into her vagina before it fully closed, probing her opening. She pulled apart her lips and give me room to go deeper. I was now tasting my cum, mixed with her copious juices.

"Oh, don't stop," she cried as I backed away for a moment.

I pushed a finger into her still stretched hole and licked her clitoris. Adding a second, and then third finger, I fucked her as spread my fingers, expanding her hole. Then I pushed the tip of my tongue back in, getting deeper this time

Again withdrawing, I pushed two fingers back in, then added a third. She humped against my hand.

"Oh, this is so cool. Keep going."

I added a fourth finger and spread them apart, stretching her vagina while I diddled her clitoris with my tongue. She climaxed moments later and we cuddled together, two new lovers.

"Randy, I love everything we did. How many fingers did you get into me?"

"Four."

"I was surprised it didn't hurt. I guess it didn't stretch me much more than your big cock. Next time you do it I want you to stick your cock in and see if it feels any different. Are you going to keep seeing Nancy? I don't mind."

"You don't?" I was very surprised.

"No, not at all. She thinks the world of you, says you are the best she's had. She likes lots of sex and I think you should stay involved. Provided, of course, that I become your number one girl."

"You are definitely number one, Jenny."

"I have another reason for being so altruistic. Nancy and I have a relationship. It started almost a year ago and was one of the reasons I moved in with her. Does that bother you?"

"So the two of you do what, eat pussy?"

"Yeah, mostly eat pussy, play with some toys. My favorite is when she's fucking me with a dildo while licking my clit. Really gets me going."

"And how do I fit in?"

"We want to share you in bed. You can watch us play and fuck us both. Of course I want plenty of time for just you and me, and Nancy expects her share. Doesn't that sound exciting?"

"God, yes. And here I thought you were this sweet, virginal girl."

"Just because I like sex doesn't mean I'm not sweet...."

Our new three-way arrangement was a success from the start. I was fucking Jenny three or four times a week and Nancy once or twice. That seemed only fair since she had two other guys to keep her busy. The girls also continued their loving and made time for all three of us.

****

"Randy, is our relationship for real? I mean, I've gone from infatuation to lust and now love. I know I'm still young but I want to be with you, forever."

"I feel exactly the same way. I love you very much and am hoping we will get married when you graduate. How would that be?"

She hugged me tightly and cried on my shoulder. "Oh, yes, Randy, I love you too. I want to be your wife. Two years seems such a long time, though."

"What about Nancy?"

"As far as I'm concerned she can stay a part of us as long as she wants. We get along really well and the sex is very exciting, don't you think? You are getting two pussies and we get to play."

"It does seem to be working out rather nicely."

"Honey, have you had lots of girls? We've never talked about our prior relationships. Nancy went on and on about what you guys did in bed. It turned me on. That's why I surprised you on our third date, I wanted to find out myself. What a great cock you have and I love how you eat me, especially after we fuck. So tell me, how or where did you get your experience?"

"I was eighteen and very wet behind the ears. My sister, a couple of years older, decided I needed some education and hooked me up with one of her friends. Mary was her name and she was my first. My sister invited her over one evening. I suppose it wasn't 30 minutes later and we were nude. She gushed over my cock, which made me feel really good."

"She said I had a one in a million cock and girls would beg me to fuck them. I figured it was just BS to help reduce my nervousness. Anyway she sucked my cock and I lasted maybe a whole minute. I was so embarrassed but she said that was normal for a first time. Then she laid down and pulled me to her, positioning my already stiffening cock to her pussy.

"I wanted to shove it inside but she held it by the shaft so only the head could penetrate. After I settled down she had me move in and out, still keeping her hand on my cock. A couple of minutes and I was squirting against and inside her pussy. I was mortified but she said that I needed to get that out of my system and now we could fuck as soon as I was ready again.

"She took my cock into her mouth and gave me my first blow job but stopped as soon as I was hard again. Then she got on top and dropped down on me. She did all the work and I exploded into her pussy. It was exquisite, much better than the first two times. Thinking back, I don't think she climaxed even then, but I wouldn't have known the difference. The second time we got together I was still way too horny and squirted before she was ready."

"She told me not to worry, that I will learn how to pace myself, but now she needed some relief. She wanted me to eat her pussy. I knew what that was about, of course, but knowing and doing are two different things. She pushed my head down to her crotch and spread her legs."

"She told me to lick her and stick my tongue between her pussy lips. She coached me on what to do. Some minutes later she clamped my head between her legs as she came with a violent shudder. I felt really proud that I did so well. It was only later that I realized that her pussy had been full of cum and I was tasting both of us.

"We had sex five or six more times over the next couple of months. I remember everything we did. I guess that's to be expected for first times. And then she said good bye. Later I dated a neighbor girl that I had known since grade school. She always seemed to like me and I figured maybe there was possibility. She was a virgin and we fucked on the second date. We dated for about six months until she and her parents moved away. I went out with a few other girls but nothing serious.

"In college I met a girl, Joyce, and fell in love. We dated for a year and got engaged. It didn't work out."

"What happened?"

"I came back to our apartment early one afternoon and found her with two guys in bed."

"So you dumped her?"

"I was obviously very upset and felt betrayed. She said it was one-time thing and maybe we could have gotten past it. But when the word went out that I caught her in bed, a couple of girls clued me that it wasn't the first time and not first guy. So we split. I graduated from college and hired in at Acme, and met Nancy."

"She said she was the one that put the moves on you."

"Yeah, we met at the local after-work bar and were in bed an hour later. After Joyce I wasn't ready for a relationship. So our friends-with-benefits situation was perfect. She's a great gal and we hit it off in and out of bed. After you and I had sex that first time I intended to break it off."

"She told me. Did it bother you that she was fucking other guys?"

"No, she made it clear from the start that she liked sex and variety, and anyway I wasn't ready for any commitments. It was the right situation for where I was at that time."

"Now I want to tell you about me."

"Jenny, I love you for who you are. You don't owe me any explanations." Actually I was concerned I might learn some things I didn't want to know.

"Well, you know I wasn't a virgin when we met and on our third date I was the one who practically attacked you. God, I was so horny for you. But there's more and I want it all out in the open."

And so Jenny told me her story.

*****

"What are you guys doing? Oh ..."

My brothers were watching a porn video. I stopped and stared at the graphic scene. Two guys were playing with a girl. One guy was fucking her from behind while the girl was sucking the other guy's cock.

"Do you want to watch? It's good," my brother Jim asked. "Come on, sit down. Learn something."

There was something mesmerizing about the video. The actors were attractive and the girl seemed to be having fun. I had never paid much attention to porn but focused on the huge cocks.

"Want a beer, Jenny? And we got some weed."

I tried it a couple of times in high school. Several of my girlfriends did it regularly but I didn't know if I liked it or not. It was kind of cool to break the rules but it made me horny. It didn't help that my friends would graphically describe the things they did with their boyfriends while they were stoned. I was still a virgin.

Some smoke and a couple of beers later I wasn't feeling much pain. The second video was similar, two guys and a girl.

"Jenny, that girl looks just like you, don't you think?"

It did, more than just a little.

"Can't you just imagine that's you with those two guys and their big cocks? I'll bet they would like your tight little pussy. You still a virgin or has your boyfriend fucked you already?"

"Come on, you guys. No, he hasn't. I'm still a virgin and intend to stay that way for quite a while."

It was brave talk but she and Joe, her boyfriend, had been getting more intimate. Her last date he had actually pushed a finger inside. It felt good and made her all tingly. Watching the porn video was making her horny, no doubt partly the effect of the weed.

"What are you doing?" I exclaimed as Gene unzipped his jeans and pulled out his hard cock.

"I'm going to jack off. Jim, how about you?"

"Yeah, I can't watch much more without getting some relief."

"I'm going to bed," I declared but continued to stare at my brothers' hard cocks.

"Want to touch it?" Gene asked.

"God, no! You guys are awful." I got up and wobbled off to my bedroom, head spinning from the weed and too many beers. I stripped off my clothes and crashed on the bed. Sometime later I felt someone get into bed with me.

"Relax, Jenny, it's just me," Jim murmured into my ear. "Turn over."

I turned onto my tummy, still groggy. Jim took advantage of my condition and pulled down my panties, my tight little ass now exposed. Damn, she was sexy, he thought, as he gently massaged my back, gradually working his way down to my ass. He nudged my legs apart to give him access to my pussy.

I don't remember much more, but my brothers filled me in what happened.

"You going to fuck her? I'll get the camera." Gene asked from the doorway.

"Yeah, I've been wanted to do this for a long time. Now that she's eighteen, why not? She may be a virgin but you saw how she stared at our cocks. Go get some lubrication, she's probably really tight."

Jim placed a glob of lotion on my pussy and rubbed it around. He finger-fucked me and then used two fingers. My pussy was lubricating. He placing the head of his cock between my lips and moved it up and down several times. Stopping at my vagina he pushed the head in about half an inch. He said I moaned and wiggled my hips slightly. Encouraged, he pushed in further, his cock head now inside. Then back out.

Jim was now fucking me with two inches of his cock. I moaned and pushed my ass back towards him with each small thrust. He looked at his brother and smiled. "I think she's ready." He shoved past my hymen.

I remember screaming and trying to pull away from whatever was penetrating between my legs. The pain was momentarily intense. I wasn't Jim's first virgin so he expected the reaction and held my hips, keeping his cock embedded and steady.

After a minute he slowly and carefully moved deeper. He said I groaned as he began to fuck but stopped trying to pull away. He lasted only a few minutes before filling my pussy with cum. He got up and Gene took his place.

"Better use some lotion. She's really tight."

Jim took more pictures as Gene fucked me. This was blackmail insurance in case I raised a fuss. He got some good close-ups of my gaping pussy with cum leaking out.

"I want to do her again," Jim said as Gene pulled out. I grunted as he shoved his cock into my gushing pussy. Having come once he lasted a long time.

Several hours later I woke up, my crotch hurting like blazes. Stumbling to the bathroom I peed and wobbled back to bed. In the morning I knew something awful had happened. I was nude, no panties, my pussy hurt and there was blood on the sheets. I guess I became hysterical as I finally realized I had been raped. And by my own brothers. How could they?

I slowly walked bowlegged to the bathroom and sat on the stool, examining between my legs. My pussy lips were red and stuck together with cum! I took a shower and returned to my bedroom. God, look at that sheet. I stripped the bed and laid down on the bare mattress and cried.

A couple of hours later I dressed and went into the kitchen. Both my brothers were drinking coffee, just like normal.

"How do you feel, Jenny?" Gene asked.

"Fuck you. You guys raped me. How could you, my own brothers?"

"We didn't rape you, you watched the porn videos with us, watched us jerk off, and then invited us to your bedroom. You know you wanted it and we gave it to you. Sure, you hurt for a moment but after Jim finished you wanted me. You're a really sexy girl, Jenny. You didn't expect us to turn down an invitation."

I was now very confused. I remembered the videos and seeing their cocks. God, I should never have done the pot and the beers. I remember someone rubbing my back and touching between my legs. So maybe it was true, I wanted to be fucked.

"I don't believe you. At the least you took advantage of my condition. That pot shit and those beers. I'm going back to bed." I spent most of the day in bed, crying and feeling sorry for myself. Two days passed and their parents were out again. Her brothers showed me the photos.

"Really sexy, Jenny, don't you think. Great ass and really tight pussy. Look at this one. I just finished and you can see blood on my cock from your hymen. No doubt what just happened. And here's one where Gene pulled out and your pussy's gaping wide and cum is leaking. I fucked you a second time after he finished. Here's another one afterwards. Lots of cum. I suppose you were pretty sore afterwards, your first time and three fucks. Next time we can take some video so you can see what it looks like from behind."

"You are crazy if you think I'm going to let you fuck me again. No way! When mom gets home I'm going to tell her that you guys are perverts. I hope you get locked up."

"Come on, Jenny, it wasn't so bad. Look at this picture, see, you have a little smile on your face. Does that look like you are being raped? And your pussy got all gushy. It's just like we said, you came on to us and wanted it. Sure, you being our sister we should have said no. But come on, we got horny watching the video and showing our cocks to you. What did you expect?

"Anyway these pictures would be really embarrassing if they got posted. It's easy to see its you in the picture but just our cocks are visible. Just think what our parents would think, not to mention your friends. Look, we know your first time hurt but that's all over with. We know how to make girls feel really good. Just give us a chance."

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