The Other Shoe Ch. 02

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Jason goes in deep, and Sherry falls hard.
4.1k words
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Part 2 of the 3 part series

Updated 06/09/2023
Created 07/03/2019
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As we snuggled together, my hands roamed all over her body. I thought I might be able to fall in love if she was all of the sexy parts of her twin, yet sweet and innocent and girlfriend material. Trainable girlfriend material.

Sherry's body was magnificent and I wanted to really compare her to her twin by getting inside. Kerry was magnificent in bed and had strong muscles and didn't feel loose, but if her virgin sister was every bit as fit and even if she had half the skills and her tunnel was thus far unexplored...that might be fantastic!

The handjob she gave me earlier hadn't satisfied me, and since I hadn't made a deposit inside her pussy yet, I eventually had her talked into sitting in the chair with her legs draped over the side, opening her up. The view was exquisite! I played around with one finger but she was too tight for two right away.

"Why do you like doing that?" Sherry asked.

"Because you are beautiful and your body is...just fantastic! Sit back and enjoy this. Try and relax and I think you will like this," I reassured her.

I was going to use a trick Kerry taught me. I had my right middle finger inside her and rubbed upwards, like I was motioning her to come here. Kerry called that move the "Cum Here", for obvious reasons. I started rubbing her clit with my right thumb at the same time, but as she started to get into it more and once I started to hear her pussy slosh and slap, her breathing pick up, and her fabulous breasts flush and nipples get as hard as diamonds, I started to use my left thumb and push down gently on her mound and hair, right on top of where my right finger was rubbing. The angle was uncomfortable for me, bit for Sherry blended sensations were... EXPLOSIVE!

Just like her sister she squirted. Squirted all over the chair. Sprayed my chest and then I put my tongue down there and sucked on her dark pink, almost purple swollen lips. By this time her hole was gaping as much as it probably ever had before, and it just screamed out to me, "Drive your cock into me, PLEASE!"

I was so horned up and had a Purple Helmeted Warrior raging for battle so I put my hands on the arms of the chair and lined up. I rubbed the head of my dick up and down her lips, getting them slicked up with her juices. The sticky connection we made got me ready, and just as I was going to plow into her, she stopped me and said, "W-what are you doing?"

I couldn't tell her this is what her slutty twin wanted so I said, "I am so turned on, I just neeeeed to be inside you right now." Never one to beg or sex before, I almost said "puh-leeeeese" but didn't.

"But I need to save myself for that someone special," she retorted.

My raging boner all of a sudden was deflated by about 50%. Fuck! She was unintentionally toying with me, and it was killing me.

"Would you like me to, um, lick it, like you licked me?"

Well, the mechanics and techniques would be different, but something was better than nothing. Actually, I had something. Blue Balls.

"Only if you want to," I assured her.

She took my cock and played with it a bit. She was better with it this time than she had been her first time, and I could see that she was psyching herself up, and all of a sudden she lunged forward with her mouth and her gag reflex kicked in, and she quickly withdrew.

"I'm sorry...I can't. I mean, I don't know what I am doing," she said, tears in her eyes. They may have been from emotion or from gagging.

I wanted her to succeed. Personally, selfishly, I NEEDED her to succeed. But for her own confidence, I wanted to help her. Did I want to turn her into a slut like her twin? No, but I had hoped to turn her into possibly my girlfriend with many of her twin sister's sex skills which were legendary.

"Here, let me lay down, and you explore me. You can lick it, suck, touch, and ride up and down- not penetrating, but just explore," I said.

I laid down on the floor and she sat beside me. We were both completely naked, and she did feel comfortable with that. She started by touching my chest, tracing the muscles down my abdomen to my crotch. She played with my pubic hair, and gently touched my balls. I was fully responding by this point, and she stopped, came up to me and kissed me, and said, "Thank you. You want to have sex, but I am not ready yet, but I know enough about anatomy and biology to know this is tough for you. And you have done things to me that...a book could never describe. Thank you, Jason, for being so generous."

Now I felt like a shithead, so about all I could say was, "Do what you feel comfortable with."

She switched her body position around so she was facing my feet and her butt was near my head, but far enough away I could grab her globes. Her body was amazing, a treasure to be admired. God I wanted to fuck her, fuck her hard, make her scream my name while I fantasized about...her. I wanted to be with Sherry the Virgin and not her slutty twin Kerry. Even though my night had been full of ups and downs, I wanted to go at her pace, so while she was exploring me, I explored her yet again. I grabbed her left ass cheek with my left had and cupped her globe, and put my left thumb inside her. She was still pretty tight and tensed up a bit, but then relaxed. Eventually she tried sucking me and did okay, but stopped before I came, like she could sense something was about to happen.

We were both breathing hard and she decided to try something new and bold. She straddled me and ran her lips up and down my shaft. I was still technically outside of her, but she got some of the sensation of having me inside of her. She was wet and sticky and we blazed a trail of sex juices along our parts, and then I announced, "Sherry, I'm gonna cum!"

She slid back and looked down to see the tip of my cock peaking out from behind or under her outer lips. She touched my head, gently squeezed and I erupted all over. She touched my cum and rocked a bit, feeling it inside her outer pussy.

I was finally satisfied. Had I picked up Kerry, I ould have had meaningless but fantastic sex. However, I was kind of forced into accepting the virgin twin sister, didn't penetrate that gorgeous body but hoped it could lead to more.

************************

We lay on the couch several hours later, still naked and cum covered, both enjoying the touch of the other. "Lovers" may or may not have applied. I wasn't in love with her-yet anyway- and we really hadn't "made love" yet. That was way down the road. But sex pretty soon was on my mind.

"Jason, what's going on here?"

"Well, Neal is a con artist and Peter is the FBI agent who arrested him. Neal is out of jail but has to help Peter catch other white collar criminals, thus the name of the show," I said. I knew what she meant, but felt like it was too early to have such a serious talk. The fact of the matter was, I didn't know what was going on. I had very little emotional investment so far.

"I mean, with us, Silly."

"I don't know. I mean, I want to...be close, but we go to different colleges, and just met."

"Yet you want to sleep with me? Fuck me? People should get to know each other first. Maybe even be married first," she said.

She had a point, but people had one night stands or sex before marriage all the time. I tried to think of a response, but before I could, she continued.

"Have you slept with Kerry? I know she's slutty, and you know her and she talked nicely of you. Have you two ever...?"

"Yes, we have." I figured there was no point in lying.

She looked me in the eyes and kissed me, and said, "Thank you. She told me you two had and that you were a generous lover. She kind of pushed me your direction last night. But I am nervous. I am a virgin athlete on an athletic scholarship who's sister is wildly popular with the men because she's...good at what she does."

Once again, I had nothing to say so I waited for her to go on.

"If we...did 'it', would you fantasize about ME or Kerry?"

I looked her in the eyes, and told her the truth, "You, Sherry."

"Bullshit. I have no skills and Kerry is a pornstar. I cannot nor will not try and compete with that, so why ME?"

"Because of your innocence. Kerry is great at what she does and enjoys it. But she does it for...selfish reasons. If you and I...do it...it will be for other reasons."

"Who says I want to 'do it', Jason?"

"When you do want to 'do it', Sherry, maybe you will remember me. Maybe it will be with another guy, but maybe you will remember how nervous you were and also remember the pleasure you allowed yourself to feel. Sure, I'd love to go into my bed right now and have sex, fuck or make love with you, but only if you want to. And if you wait until your wedding night and you look into your husband's eyes, the true love of your life, I don't want you to think of me, I want you to think of him and all the pleasure you know you have the capacity to feel. That's all. Sure, I like you, I think you are cuter than your twin, and I think you are pretty. And your body is fantastic! If we had meaningless sex, that would be great...for me. But you deserve better."

It was borderline great performance and borderline heartfelt emotional spilling. Sure, I wanted inside Sherry, but I also wanted a girlfriend, a lover, a partner. I was trying to get laid, but I had my eyes on something off in the distance; a beautiful sunset viewed by two.

She looked at me, and started to say something, then bit her lip, started, and finally said, "Jason, be my first. Take me onto your bed and arms, and make me feel special. I have never...I'm not...my sister, and I want it to be special."

We were still naked, so that part of foreplay was taken care of. I held my hand out to her, snd she took and and followed me down to my bedroom.

"Jason, I'm not on any...protection. I used to be, but since I..."

I held my finger up to her lips, "It's okay. I will use a condom. We will be fine."

Now she seemed to be nervous and talking a lot, "My last physical said my hymen was no longer present. But my virute and womanhood..."

Once again, I tried to calm her down, " Shh shhh shh, it's okay. All of this clinical talk, 'hymen', virtue', 'womanhood' is, uh, kind of killing my 'manhood'. I realize some of the other words may sound vulgar, but basically I want inside you, and you want me inside of you. Just go with what feels normal."

I hated to have this talk right now. Sherry was my first virgin, and I guess all of it was kind of new.

"Then fuck me hard and make me scream," she said. That-a-girl!

I still went slow. We kissed, I stroked her fantastic body. I rubbed her pussy. She played with my hard cock. Finally she said, "I'm ready, Jason."

I laid her back on the bed and she instinctively parted her legs, allowing me access to her thighs and my prize. I took a condom off of the bedside table and rolled it down my shaft. I looked into her eyes and she nodded almost imperceptibly. I touched her outer lips and she flinched, and I pushed inside with just the tip. She gasped slightly, so I went a little further. We did this 3 more times and finally I was balls deep inside of her. She had a mixture of pain, pleasure, excitement and fear in her eyes. I asked, "Are you okay?"

"Yes...it's...I just feel so full. I never thought it would fit," she said.

"If you're okay," I said as I withdrew and slowly thrust my entire length back inside her.

"Uh Ooohhhh, that feels..."

She never finished because I repeated the process and repeated it again.

My rhythm picked up she responded accordingly. Maybe fucking was genetic because in no time she was responding just like her twin sister. "Oooh yeah, fuck me Jay. Fuck me. Fuck me hard!"

This talk was a far cry from her clinical speak only moments ago. I was getting close and sensed she was, too. I just needed to hold off a few more strokes...

"Oh fuck yeah! I feel that same feeling again...OOOOOHHHH SHIT! I'M CUMMING! FILL ME UP JASON AND MAKE ME CUUUUMMM!"

Her pussy clamped down and spasmed around me, and then I let go. The hormones and chemicals in my body were released along with my orgasm. As I hovered there over her in a push up position, twitching dick inside her, feeling her pussy spasm around me as I filled her up, and I felt empty. I cannot explain it, but I felt empty, then something else started to creep in.

Sex with Kerry had been great. Sex with other partners had been great also. Sometimes we had wanted or thought about it going further. A girlfriend of almost a year I had had always meant special sex, even after we broke up finally. But sex with Sherry had been...empty. I didn't feel like I took advantage of an innocent virgin, I just felt like I had slept with a mistake. And I felt horrible about it, but knew it was going to get worse.

We cuddled, but my mind told me I needed to look for an escape route. The consciousness Angel on my right shoulder said, "You reap what you sow, Jason. You want to plant good fruit," while the Devil on my left shoulder said, "That's fine. You got some. Might as well do it again. Leave your seed, then leave her."

Eventually I excused myself to go to the bathroom. I took the condom off and tossed it into the trash, then I did my business, looked in the mirror and was not happy with the man looking back at me. He looked older and worried. Then when I opened the bathroom door, Sherry was standing right in front of me. I jumped.

"My turn," she said.

As she did her thing, I quickly threw on some clothes, getting dressed. No more sex. I needed to get her to her sister's place and hope to escape. At least the condom held.

Why did I have such a bad feeling about this? Guilt? Shame?

Fear. It was fear. But why?

I promised her lunch and then to drop her off at Kerry's place. She said she couldn't get a hold of her sister and asked me to take her home, over an hour away. We grabbed a quick bite to eat and the entire time in the car she asked about my dream wedding and told me about ours, I mean, her dream wedding.

I felt sick. I was in over my head and felt obligated to her for a couple of weeks anyway. At least we went to different colleges.

I walked her to her room, and her roommate was there. Her roommate had been in the shower and still had a robe on her body, a towel on her head, and big glasses on her face. I found out her name was Lori and she was a civil engineering major who blew her knee out playing tennis. "I would rather be a Con E major, but we don't offer that here, and they paid me to play tennis until...Anyway, tell me about your classes, Jason."

I told her about being a construction enginering major while Sherry looked on. Eventually Sherry had had enough and interrupted us. She possessively held my arm and eventually I was able to leave and head back home. I had plenty on my mind. Lots of good thoughts, thoughts of Lori, and thoughts of Sherry. Those were a little more cloudy.

****************************

On Tuesday I took the bathroom garbage out, remembering there was a soiled condom in there, but didn't see it. Maybe Sherry had seen it and flushed it down the toilet. Some day some plumber would be pissed when he had to dig that out.

****************************

In Wednesday after I met with my tutoring student and headed back across campus, I saw Kerry. I never saw her on campus.

"Hi, Lover!" She yelled.

I replied more tactfully, "Hello, Kerry," then realized my mistake.

It was Sherry. She was here. On MY campus.

"Lori is transferring down here next semester and I came down. I forgot I drove down here last weekend and Lori brought me down to get my car, but it has been towed. Hey, should I transfer down here next semester? Maybe we could share your apartment?"

This is why I had a bad feeling. It was starting to make sense now.

Sherry, I-" I started, but she cut me off.

"If we save money, and if you ask me to marry you..."

Fuck. This needed to end. But how?

"Sherry, I am nowhere CLOSE to being ready to get married."

"You will be. What we have is special," she said. It was no big deal. It seemed to be a forgone conclusion in her mind.

"I have an appointment in an hour, what do you want to do until then, huh, Lover..."

"Sherry, I have class in 10 minutes."

Just then, Lori came up and said she was transferring next fall, and I offered to take her to a class that she would need next year. The instructor was my advisor and also the man Lori had just met with and he was the one who offered she could come to his class. I offered to lead her there.

"Can I come along?" Sherry asked.

"There is no extra room, sorry," I said. Talk with Kerry, and maybe we can meet later," I offered. That gave me an hour to figure out an excuse to get out of it.

******************************

"So, Jason, Sherry said you and her are engaged? Or engaged to be engaged anyway," Lori said as soon as Sherry was out of sight.

"Uh, god, no. I feel like she is a stalker. Her sister stuck me with her, and she stayed over because her sister..."

I filled in Lori, leaving out most of the scandalous parts. Sherry had told Lori everything, however. Including the missing condom from my bathroom. Lori said she saw it in Sherry's laundry.

"Jason, watch out. Sherry is crazy."

"Her sister is fine, but not 'girlfriend' material. I had hoped Sherry might be, but..."

"She's batshit crazy. I know, I am stuck being her roommate. Another good reason to transfer away. She's a good tennis player, but even that fact doesn't change the fact her aura puts strain on everyone around her."

I felt relief. My gut instinct was right. I needed to get away from Sherry. Now.

I had planned on doing it Saturday because I had a big test on Friday. But I needed out. Now. I would help her get her car from the impound lot, and tell her not to call me anymore.

I just needed to let Lori know so she wouldn't get caught in the crossfire.

After class, Lori and I exchanged numbers so she had a contact next semester. I really had a good feel for Lori but feared I had screwed it up because of Sherry. Damn, thinking with my dick ruined any potential chance with Lori. At least sex with Kerry had been No Strings Attached, and fabulous. Next time I wanted to have sex, I needed to say "no".

Lori left campus for her dorm and planned on being gone when Sherry would arrive. I took Sherry to the impound lot, and when she had her keys, we had a talk. I told her she was smothering me, I knew about the condom, and felt scared, threatened, and creeped out. She cried, said she would be less smothering, and wanted a second chance. I said, "no".

However, I did relent a little and said I would come up to watch her play tennis. That gave us a few days to rethink this "relationship", but I told her, under no circumstances would we have sex. Everything would be done in public, and I would not go to her dorm until we had time time to talk.

Sherry agreed to my ground rules. I bombed the test on Friday, and Saturday I dreaded the drive up to watch tennis. I had talked to Lori a couple of times after "the talk" Sherry and I had. She was aware of the details and said she would see me at the tennis matches.

Damn, I wish I hadn't screwed that one up! Lori was fantastic, and Sherry was crazy. Hopefully Saturday I could get the clean break I desired from Sherry and next semester Incould start something with Lori. But in my experience women didn't like to personally know women with whom their boyfriends had slet with before.

********************************

College tennis generally is not a spectator sport, at least not at Sherry's college. No place to sit, hard to see, and no public bathrooms. I was a nervous wreck until I saw Lori. She was in a tennis warm up top and a tennis skirt. She said she didn't compete anymore, but looked the part. I told her I needed tonuse the restroom and where was it. She took me to their dayroom and would let me use that one if I promised to help her carry Gatorade bottles back. I said I would.

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