tagAnalFor Claudia Ch. 03

For Claudia Ch. 03


Tonight's entertainment was John, or "Johnathan" as the pretentious medical student liked to call himself. We had met on eharmony. I was happy to be one of his Internet conquests. I began by holding him in my mouth for a bit to easily bring him to full hardness. He had a decent size and a good smell. I always sucked a man's penis briefly before allowing it to penetrate my vagina. I just didn't feel comfortable skipping that step. I'm not exactly sure why, but I think it was because I could evaluate him with all my senses and really get to know what was about to plunder my reproductive system. I guess it was a form of safety net. He passed the test, and soon was fucking me in missionary position, occasionally kissing me, and occasionally reinserting his penis when he carelessly let it flop out. He was bad at fucking, and he was mediocre at kissing. At least he smelled good, was reasonably handsome and intelligent, and was a nice guy. He had some game. He certainly had no trouble getting me into bed. But once here, he was a clueless, lost soul. I would enjoy tonight's sex somewhat, but he wouldn't be getting a third date. At least he was better than last night's lay.

I would say my slutty behavior was making me worry about getting men to fall for me as a realistic long-term prospect, but last night's date had left two voicemails already. I was 100% sure John would call me tomorrow too.

My mind wandered for a bit, as I imagined he was someone totally different. I alternated between better sex I had before and sex with certain celebrities that I wanted to experience. Then I gradually came back to the present. John had been fucking me for about two minutes, and I knew he was about to blow. I grabbed his ass-cheeks. They were firm. At least he believed in fitness, presumably since he was going to be a doctor. I was blessed with a pussy that self-lubricated very well since he didn't spend much time on foreplay, and I worked to keep it fresh and tight. I gripped him enthusiastically and said just the right things to bring him off. If he was a little more skilled, I would have offered to have him ejaculate on my face or something, but I thought that would be a little ambitious for this man to pull off without more practice. Sure enough, after a few more second he began talking to God, and then he quickly convulsed and poured himself into the condom that I had made him put on.

As he softened, he kissed me softly. It was pleasant. Then he pulled out and went to clean up. I correctly assumed we were done. Unless he liked the taste of rubber and enjoyed going down on a woman after he got himself off, I knew I'd be getting myself off later. John offered for me to spend the night, and I'm certain he was sincere. I declined respectfully and thanked him for a wonderful evening.

When I left, I knew I'd never talk again to this nice, nerdy future doctor that wanted to save the world and would even probably be rich one day. Why? This guy had tons of potential. But deep down, I knew the answer. The two men that made love to me first stole the show. To win me over, a guy needed to touch my heart like Lance did, or my cervix like Bob did. It was hard to find a man that could do either.

It had been about a year since that torrid night with Bob and Jen, followed by a nightcap with Lance that kick-started our relationship. I didn't have sex with Jen or Bob again after that night. They did not approach me for a repeat performance, perhaps because I had lost some of my mystique when my cherry was taken. Or perhaps since I was in a relationship now they figured I needed to just focus on Lance. But they were very friendly every time I saw them in church, which incidentally put my mind in the gutter for the entire sermon. Perhaps they were waiting for me to approach them, which I never did. Only once at a party did Jen and I even act like anything had happened. I met her in the stairwell outside the apartment we were at and and just gave her a quick kiss. We smiled and moved on.

Lance and I were a great couple for about three months. After that I don't for sure how or why it happened, but everything fell apart. I think the slutty way I acted the first night we spent together finally caught up with me. When we broke up it devastated me, even though I could tell it was the right thing to do. My old tricks emerged quickly again. I wasn't perfect after all. I took my new-found sexuality and put it to use, getting a lot of dick. In my defense I was sort of looking for a relationship, but I went out on a lot of dates from people in my different social circles and on internet dating sites. I gave it up pretty liberally, sometimes on first dates. I had a great time being an easy lay and slowly replaced my innocence with more and more sexual skill as I evolved as a lover. I was wiser this time and steered away form men at church and work. I thought if I wanted to bang a lot of guys, that was my business and people shouldn't judge me, but I was aware of the attitudes and double standards of the world I lived in. I took the necessary steps to protect a reputation I didn't deserve based on societal norms.

At least I was more aware of safety after the first night. Only Lance and Bob ever had the privilege of riding me bareback, let alone coming in my pussy. I became very good at getting men to ditch the condom just in time to explode on my face, since I loved when men did that. I felt whorish and guilty of course. I was still religious. But I had fallen into a life of sin, partly because I was in a dark place after Lance and I broke up, but mostly because I was simply way too horny.

Anyway, while I was getting all this dick, Lance and I stayed in touch, and occasionally we used each other for a booty call. We kept it casual and didn't discuss who each other was dating or anything like that. There were maybe five or six of these during second half of that year. Then Lance's unit got notified that he was going to Afghanistan again. I was upset. I knew we might never be a couple, but a man I cared about was going back into harm's way. I called him up a week before his deployment. He was leaving to spend a few days of vacation with his parents, and this turned out to be his last night in town. After small talk, the conversation went something like this:

Me: "It's your last night in town. I hope someone is taking care of you. Do you have a girlfriend? Or is someone going to step up and 'take one for their country?'" I was referring to the phenomenon where women pick up men in bars that are about to deploy and give them gratuitous sex. Here was one man that deserved it.

Lance: "Haha, nothing like that. Just relaxing here at home."

Me: "No way, Lance. Come over tonight about 8:00. I'l make sure you're sent off properly."

Lance: "Why are you so good to me? I don't deserve that from you."

We went back and forth, then he enthusiastically agreed.

I thought about what I could do to send him off properly, and an idea began to take shape in my head. I would call Jen. It was Friday night, so she probably had plans, but it was worth a shot. I had heard she stopped hanging out with Bob, since he had moved a few hours away, and they were never really steady anyway, at least officially. I decided to make it a little exciting for her. I sent her a text: "You are the sexiest woman in the world." It was dorky and perhaps unoriginal, but I got her attention.

She came back a couple minutes later with: "That's how you make me feel. What can I do to make your day better?"

Me: "If you don't have plans tonight, I have an idea."

Jen now was texting me back right away. "My plans were to hang out with you."

I was happy to see that response. Although I was sure she already did have something to do, and I had just talked her into something else. "Come over about six. We will stay in, but may I suggest a cute pair of jeans and some nice undies."

I had time to visit the sex shop about half an hour away, the one that was smart enough to have drive-around-back parking. I bought the props I needed. My thong underwear always felt good riding between my butt cheeks, but today that took on a whole new meaning, serving as a constant reminder of my cute butt and the tight hole in the middle and the potential the upcoming night had to offer. I got more excited as the day wore on. I'm embarrassed to say that I even reached into the back of my jeans while in the parking lot and just gently rubbed my anus for a few minutes just teasing the entrance. I had never played with my backdoor before or allowed anyone else to, and suddenly it seemed very erotic. I wised up and stopped, seeing as how I was in a public parking lot still.

I spent some time on the Internet researching anal, being the nerd that I am. I knew a lot already, but my "research" made me more prepared. I was very happy. I owed Jen a threesome, and I was about to deliver. I already knew with a little coaxing both Jen and Lance would go for this, or else I wouldn't even try, because it might be disrespectful to just assume.

I hit the gym hard for an hour. Feeling refreshed, I showered, shaved my pussy, and put on some nice jeans and a cute top. Jen arrived fashionably late. She was worth the wait. Her long, blonde hair was styled perfectly, and she had great jeans on and a nice top that was showing some cleavage. It wasn't a top I had seen before, since it wasn't appropriate for her church crowd, which was the only place I ever saw her. She was well put together for sure. It was great to see her again, and we hugged for about a minute at the doorway. I really missed those breasts mashed against me. More important than that though, I had my cool friend here with me again. I had wasted the last year not hanging out with her and getting t know her better.

"So, I do have an idea for us but I think we should relax and have a drink first and catch up before I run it by you. We have a couple hours. How does that sound?"

Great!" she said.

I had some premixed Long Island iced tea, so we both nursed one of those while we talked. They were strong, and I could feel my inhibitions lowering with each sip. Jen was on the chair with me on the couch in my townhouse living room. First Jen brought me up to speed on her life. She was dating casually, but Bob was pretty much out of her life, although they stayed in touch via Facebok and stuff. He wasn't fucking her any more, probably just because of geographics. There was one guy she dated until a few weeks ago. He was the only guy she'd put out for besides Bob in over six months. She said it just wasn't the same. He wasn't as cool, didn't treat her as well, and just didn't have the hardware Bob had.

"Your man crowned me a size queen the night he broke me in," I told her. "I like sex with all kinds of men, don't get me wrong, but the bigger, the better. Was it the same way for you?"

"God no. He fucked me for months before I got used to him. Once I did though, it's hard to go back to normal."

"Hmm, " I said in agreement.

I gradually eased into telling Jen about my life, making sure she was on her second drink before really shocking her. I told her about Lance first and how he had broken up. She was annoyed. "But he is so good looking, and so are you, and you are both athletic, go to church, and I could go on an on. What the hell is his problem?"

"He just isn't that into me, at least for a relationship. It's frustrating, because he always treated me very well after that night last year, and he's very honest. He's a great guy as you know, he helps everyone, volunteers, serves his country. I can't fault him. I guess if he can't love me that way, I don't want him wasting my time."

"I see, and plus he's leaving again, and that would be hard. Well are you seeing anyone else?"

"It's still hard to see him leave. It's a mess. Have you heard anything about me?" She shook her head no. "Good, my discretion is working this time. I have been fucking so much, you wouldn't believe it."

Jen smiled and looked shocked. "No way! We created a monster."

"Yes you did. I've had so much dick. Different dick, too. And Lance and I have a booty call about once a month still. Don't worry, I am keeping my emotions out of it as much as I can, and I'm still dating around."

"Liar. About the non-emotions. But I get it," Jen said. "He is a hunk, and he's familiar. I would do the same thing. I like him a lot too, I just like you more, so if I need to hate him for breaking your heart, I will." She giggled. My drinks were working. "So, you've been getting a lot of dick?" She wanted to know more.

"I usually make them buy me dinner first. But not always."

"So naughty," Jen said. "You can't have sex with five guys and act like you're an experienced slut though, Claudia."

"Twenty-ish," I said. "I've taken a liking to whoring myself out."

"Oh hell, I'm impressed, and very jealous. I want to be more like you."

"You came to the right place then! But I'm jealous that you still have morals. The good news is Internet dating helps run up the number fast without everyone else getting in your business. I don't tell my closest friends these thing even, but for some reason I enjoy full disclosure with you."

"And full frontal, don't forget you enjoy that with me, too." We both laughed. "By the way, you need to be referring to me as one of those 'closest friends' even if we only hug once a year."

"Agreed," I said. "You know I think of you that way."

There was a natural pause in the conversation. The TV was on mute, but we both looked. NBC was showing tape delayed coverage of the Olympics in London. "Let me get us the next round." When Jen came back with out third drink, I motioned for her to sit next to me on the couch. "It's about time," she said. Instead of leaving space between us, Jen sat right next to me with our legs touching.

"So I can I tell you why I asked you to join me?" I put my arm around her and ran my hand through her blonde hair.

"Yes, I'm dying to know, although we can drink and talk all night and that is fine."

"I agree, and that is the backup plan," I said. "But I do have a better idea. Firstly, of course I am going to make love to you. That's a given. Unless you object."

"I'll think about it, what else?" She was just teasing, and I could tell from her blushing and body language that she wanted me too.

"Well, I have a confession. I stacked dates. Have you heard the expression 'Take one for your country?'"

She had. And she quickly connected the dots. "I thought Lance left already."

"Tomorrow. I demanded that he come here at eight since nobody else was sending him off properly. And..." I said with a dramatic pause as we looked into each others eyes, "I want you to stay and help me send him off right, if you are interested."

"Wow," Jen said. "I am so interested. In both of your proposals. But I am worried about the same thing you were with Bob. I don't want to come between you and him emotionally.

"And I will tell you what you told me in this situation, and it's the truth. I would love to see you fuck him."

She smiled and nodded. "Well he is very hot, and interesting. And I want to send him off right also. Nice plan."

"There's more," I said, enjoying teasing her.


"Are you still half a virgin?"

"The purity of my backside is nobody's business," she objected playfully.

"So that's a 'yes' then. Don't worry, by the end of the night you won't be."

"Perhaps I could be persuaded to give it up. I've always wanted to try. He is gorgeous, and he won't split me open as bad as Bob would."

"Good. I'd like to lose mine too, and I know I'd enjoy it more if we lost it together."

"None of those guys got in your tushie? I find that hard to believe," Jen teased.

"I'm an untapped resource. Surprising isn't it? Honest to god, when I was just blowing men, they tried for regular sex less often then the men I put out for tried to get anal now. What is the obsession with fucking our asses lately?" We both laughed for a bit.

"Are you sure this is what Lance wants?" she asked.

"He's asked for anal a few times, so yes. And I know he'd love to have sex with you, because you're you."

"Thanks." We relaxed for a few minutes, my arm around her, and her hand on my knee causally. They showed the US swimming team half naked on the TV, and we talked briefly about which one we'd like to be underneath the most. Then NBC switched over to the back-story on the hurdler Lolo Jones, and reminded us for the tenth time that she was still a self-proclaimed virgin. "Okay, maybe her instead," Jen joked, implying she was more attracted to her than the entire male swimming team. I admit it was a close call.

"Well you are good with virgins," I said. "She has my butt, or I'd like to think so, so I can see why you're interested. Have you kissed a women since we were together?"

"No. Nobody's sparked an interest in me. You?"

"No. It's weird. I've seen a few over the last year I was marginally attracted to, but I had no desire to act. You're the only women that can do it for me."

"Do you think about me when you masturbate?"

"Oh God!" I was taken by surprise with her humor and direct inquiry. "Sometimes," I confessed. "Can I kiss you now?" We turned sideways to face each other on the couch. Her hands went under my arms and pulled me to her for an embrace as our lips met. Wow, I missed this. We only kissed for about five seconds, but it was enough to get my panties moist. Jen pulled back and looked into my eyes. I could tell right away her whole demeanor had changed. Our small kiss had flipped a similar switch for her too. She was focused but lost in the moment at the same time. The small talk was over.

After that tentative kiss to feel each other out that just ignited that spark in us again, there was no holding back. The history between us served to remove inhibitions further, and Jen and I began to kiss with a passion and urgency that we have never done with anyone before. Our mouths pressed together hard, our tongues darting in and out. I explored every part of her mouth. I sucked her tongue. I bit her lip. I grabbed two handfuls of blonde hair and pulled her head into me. She matched my aggression, and I felt a hand on my ass cheek and another going under my waistband right at the ass crack. It was as if I couldn't get close enough to her and was trying to merge with her. Her soft, feminine moans as she gasped for breath heightened my arousal.

This was amazing, and I was so glad I had decided to call her. After a few more minutes that left my panties no doubt drenched, Jen apparently decided to escalate things rapidly. "I'm just going to take all my clothes off now, is that cool?"

"Uh huh," I said. "You go, then I'll go. No need to wait. Five minutes kissing you is equal to an hour of foreplay with anyone else."

"I agree," she said. "I've been wet since I got in the car to come over. I kept thinking about what I wanted to do to you." God, I loved it when she talked to me like that.

She already had her top off, and soon she peeled off her jeans. Jen had on a very sexy bra and panty set. It was black and lacy, the expensive kind you wear when you know someone will see them. She took her bra off, and those tits that I loved a year ago bounced out to meet me. She slid out of her panties, and the goddess stood before me naked again. "Wow," was all I could muster for a few seconds. "You've filled out more; I like it."

"I knew you'd notice. I'm embarrassed. I've gained about five to ten pounds." Jen was pouting, but there was a hint of playfulness behind it. She had just the right balance between uncertainty in her body and confidence that she looked great with the changes. "It's frustrating, because I'm more fit than I ever have been in my whole life, but it just fuels my hunger too."

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