Wendy

Wendy prepares to do a striptease.

When: September 2007

Status: Married 5 years, one kid

Occupation: Stay at home mom

Meetings: Five

Age: 33

I met Wendy a few weeks before I met Lori.

Not a really long story with Wendy. I ran into her in a Georgia chat room on Yahoo and we struck up a conversation. She was 33, married, and had a 10 year old daughter. We chatted for a couple of weeks and struck up a pretty good friendship. No sparks or anything. She was cute though.

We did get on the phone and chat and have some phone sex. She really wasn't unhappily married, but sexually, she was bored. I had known her for four of five days when I started asking about meeting.

"I...don't think so."

"Why not?"

"It's a big step."

"It's just sex."

"True..."

"If you change your mind, I can drive over one day."

"Okay. I'll think about it."

We continued our chats and every time we cybered, I kind of felt like I was chipping away at her reluctance. I know when to pursue and when to retreat. I was in retreat mode. For awhile. Finally, one Monday morning, I saw her on-line and PM'd her.

"Hey, what's up?"

"Not much, sweetie. What are you up to?"

"Doing some work."

"That's cool. So....any other plans for the day?"

"Why? Want me to drive down to Sandy Springs?"

"I don't know....I just dropped Shelly off at school......"

"Well, want to meet for lunch?"

"Uh......"

"Still can't pull the trigger?"

"Sorry, Ryan. Not trying to lead you on."

"So what are your plans for today?"

"Housework.....not much. BRB."

"Okay."

"Back. Interested in some phone fun?"

"Sure."

Wendy called me up and I brought her to a nice orgasm. After she came, there was a pause on her end. "You win. Come on down." "You sure?" "Yeah."

I shut down my computer and hauled my ass down to Sandy Springs.

Wendy opened up the door as I came up the walk. "Hey! Come on in."

She was cute, that's for sure. Great curves.

We sat down on the couch. "You sure you want to go through with this?" "Yeah. I've had some offers, but always turned them down. But hubby hasn't been all that interested in sex the last year or so. So....why not?" She leaned over and we kissed for a couple of minutes.

We got up and headed to the bedroom and stripped out of our clothes. Wendy got on her knees and took my hard cock in her mouth and sucked me for a few minutes. Then she got up and we laid on the bed side by side and started 69'ing. She definitely needed to get laid. The minute I started sucking on her clit, she was groaning. About a minute later, she came, and hard.

I pulled my cock out of her mouth and rolled her onto her back. Time for the Pilot.

That's it. Keep going.

My cock was throbbing, but there'd be time for that. I knew if I made her cum a couple of times, she'd really be responsive when we did fuck.

She was soaked, and I went to work. I started sucking her tits and moving my hand around her pussy. My palm applied some strong pressure to her sensitive. A couple of minutes later, she started groaning. "You gonna cum for me, baby?" "YES!"

Wendy arched her back and as she started to cum, I slid my middle finger right into her asshole. A lot of pent-up sexual tension was released while she was cumming.

"Nice. Very nice." We relaxed for a couple of minutes and then I grabbed the old raincoat and slipped it on. I leaned over and started kissing her. I slid my right leg on top of her leg and her legs spread wide open. I eased up on her and slid my cock into her pussy. She groaned loudly, and I knew I was in for a wild ride.

Wendy locked her arms around my back and I started fucking her hard and fast. No build-up needed. This was just a hard and fast fuck. Her tits were shaking up and down each time I shoved my cock into and out of her. She came a couple more times and after the second time, I leaned down and kissed her as I shot my load.

I rolled off. Wendy was breathing heavily and said, "Yeah, I'm sure." "Give me a few minutes, and we'll go again." "You bet."

This pic makes me wish I had tried harder to keep our affair going.

Wendy grabbed a couple of cokes and we refueled. After we finished, I leaned over and we started making out. Wendy leaned down and started sucking me until I was hard again. As soon as the captain was ready to command the ship, I had Wendy got on all fours.

I stuck my face right in her ass and rimmed her out. Man, I love eating ass. And just about every woman I've been with loves getting it done.

After I was done, I slipped my condom on and slid in again. I grabbed

Wendy's hip and started fucking her fast and hard. She came several more times in the fifteen minutes I fucked her (like I said, I can last forever in the doggy position) and urged me to cum. I took my cock out and shot my load all over her ass.

I took the two used condoms and flushed them. Wendy laughed and said, "Good idea." "I learned the hard way once not to just toss 'em in the trash." "Yeah, I bet."

Wendy had to get ready to run some errands and pick up her daughter from school, so we grabbed a shower and got dressed.

We met four more times. Great sex, a decent amount of chemistry. She was nice, but we just didn't completely click. Basically, we were just a piece of ass to the other. Not that there's anything wrong with that. But let's face it: Sex is better when you're into the other person some. We weren't.

We never went out for lunch or coffee or anything. We just met, fucked, and went our own ways. It was more an arrangement than an affair.

This didn't end as much as it just sort of fizzled out. The last few days Wendy was barely on-line and we didn't even talk except to set up our last meeting. It was cool. I was glad to be out of the relationship and I think she was too.

For Wendy's Pics, click here (members only).

Rina

Rina relaxing at the beach.

When: October, 2004
Status: Boyfriend

Occupation: Student/Retail Sales Associate
Meetings: 2
Age: 22

I had been seeing Jackie quite a bit. But Alex was traveling like crazy and Jackie was in Michigan visiting her parents.

Screw that. I was horny.

So one Thursday night I signed onto Yahoo and went into a Florida chat room looking for some fun. It took a couple of hours, but I finally found it.

Actually, it found me.

I got a PM from a 22 year old girl. She asked for my info, and I said, "Way too old for you." "How old?" "41." "Works for me."

Her name was Rina. She was a senior at the University of South Florida and her mother was Japanese and her father was Taiwanese . We started exchanging pics and she requested some hardcore pics, so I sent her some of Lexi and I in action as well as pics of me and some of my other girlfriends. She loved them and rewarded me with a ton of pics of her own.

Soon we were on the phone making each other cum. After we were done, I really wanted to see if I could get this girl into bed for real.

Luckily, I didn't have to work too hard.

We chatted for awhile after we finished and she said, "Want to get together tomorrow? My boyfriend's down in Miami for a few days." We made plans to meet at a Starbucks close to my place at nine in the morning.

Rina was all about the sex, and that's all I wanted. A couple of days of fucking would fit in nicely with my schedule.

I got to Starbucks at nine and Rina arrived a few minutes later. We had some coffee and chatted for a bit. Then we headed off to her place.

Rina taking a stand.

We went in and went up to her room. Okay, screwing a 22 year old in her room at her parents house did make me feel like a dirty old man. But hey, you get over feelings like that.

We got in and Rina and I didn't waste any time stripping out of clothes. We started kissing and I laid her down on the bed and started eating her shaved pussy. She started moaning and grabbed my head, grinding her pussy into my face.

My hands were on her little ass, holding on tight. I started sucking on her clit, and that really drove her crazy. A couple of minutes later, she arched her back and came. My cock was at full attention, but I wasn't done with her.

I rolled her onto her stomach and started rimming her ass. Her asshole was so tight I could barely get my tongue in, but I managed. I started darting my tongue in and out, and I could hear Rina swearing and moaning. She slid her hand underneath her and began playing with her pussy. It didn't take long for Rina to cum again with my face buried in her ass.

She got up and said, "Fuck, you're good," and proceeded to get on her knees and suck my cock. I was leaking a ton of precum into her mouth and knew I better not let her blow my rod too long.

I took my cock out and slid on a rubber. I pushed Rina onto her back and spread her legs and pushed my cock into her pussy. She groaned and we started fucking in a fast, steady pace.

Rina's legs were wrapped around my waist and her arms were wrapped around my torso and we started kissing, our tongues pushing against each other. Her twin bed was squeaking like crazy, and after making her cum a couple of more times, I took one final thrust and came.

I took off my rubber and tossed into the trash. I laid back down and said, "You got another fuck left?" "Oh yeah."

I started sucking on her tits while she played with her clit. I ran my tongue over her hard nipples and moved my hand to her pussy and started rubbing it. Her hand grabbed my cock and started stroking it until it was hard.

When I was hard, Rina put a condom on my cock and straddled me and we started fucking hard again. Rina rode me like a wild woman, rocking and sliding back and forth. She felt great. She started groaning and said, "I'm gonna cum, baby!" and then threw her head back and came. She then said, "Your turn," and started sliding up and down my cock like crazy. I couldn't stand it anymore and finally shot my wad.

Rina rolled off me and said, "Fuck, that was great." She looked at the clock and said, "I gotta get going....I have to be at work soon."

"You want to get together tomorrow?"

"I would...but I have to work."

"After? I'll rent a room for us at the beach and we'll spend Saturday night together."

"Yeah, cool. Okay....I'd like that. I'm off at five."

"Shoot me and email after work tonight."

"Okay."

I got dressed and headed home. I wasn't sure if I'd get to fuck her again, but I called to see if there were any rooms available in Clearwater. Luckily, there was. It was the Holiday Inn in Indian Rocks Beach and it would run me a couple of hundred, but fuck it.

Later that night, Rina PM'd me and said that she'd be able to get off early the next day. She told her parents that she'd be spending the night with a friend. I told her to come up to my place at 3 the next day. Check in was at 4, so that was perfect.

Grabbing a quick bite to eat.

Rina knocked on my door at three the next day, dressed in a tight skirt and white top.

We drove down to Indian Rocks and checked in. The guy who checked us in couldn't stop staring at her. What I loved is that he knew I was going to fuck this girl all night. I followed Rina out the front door, and as I left, I gave him a "thumbs up". He just smiled and nodded.

We got back to the room and I ordered a pizza. While we waited, I ate Rina's pussy and ass. When the pizza arrived, Rina didn't even bother to cover up when I paid.

After we ate, Rina got on all fours and I banged her doggy-style. I don't know what her secret was, but I never got fully soft around her. She knew how to get me hard every time she wanted to get some cock inside her.

We got into our bathing suits and hit the beach. We managed to find a secluded area and we spread out a couple of towels. Rina pulled out a joint and we got pretty high. I hadn't had a joint in fifteen years or so and it hit me like a ton of bricks. If Rina wasn't enough to make me hard, the joint certainly was.

Well, you know what it's like to be high. You have absolutely no attention span. We were so buzzed that we started making out hard and heavy. I slid my hands underneath her suit and started the Palm Pilot.

Rina took off her top and pushed my hand away to take off her bottoms. I went back to jacking off this beauty and made her cum.

Rina and I started a side-by-side 69. I could feel her warm mouth on my hard cock as my head was buried between her thighs. I licked and sucked her clit and lips until I felt her shudder and cum again. I put on a condom and crawled on top and we fucked with me on top of her until we both came again.

We got our suits back on and went back to our room and finished up the pizza and passed out for several hours.

We woke up a couple of times during the night and fucked and sucked and passed out. Around 10, the alarm woke us up, so we fucked one last time and took a quick shower.

I took her to breakfast and then dropped her off at her house. As she was getting out, she grabbed her overnight bag, gave me a kiss, and said, "Thanks for a great weekend, Ryan. Maybe we'll do this again."

We never did, but that weekend was more than enough.

Rina

Rina 2

Rina 3

Rina 4

Joan

When: April to September 2002

Status: Married 7 years, no kids

Occupation: Legal secretary
Meetings: Lost count
Age: 29

I hooked up with Joan in 2002. We were both working for the same legal employment service and had been assigned to a law firm in downtown Cleveland for a month. I hate going into any large city, but the money was great, so I decided to grin and bear it. Especially because Joan was going to be there.

The week before the assignment started, my agency called me. My rep, Laura said, "You up for a four month assignment?"

"No. You know I have a short attention span."

"Suck it up. They can't be all two-week deals."

"Fine. Who's it with?"

"-------"

"No way. I've been there. Downtown Cleveland. Uh uh! I HATE commuting!"

"You'll be working for Jen again (an attorney I had worked with several months earlier)."

"Okay, I like her. The pay the same?"

"No, higher. Jenn likes you."

She told me how much more.

"Okay. I'll do it."

"Good boy."

"Woof woof."

"AND your buddy Joan will be there! She started this Monday."

"Working for Jen?"

"Uh huh! Her regular secretary's taking time off to have a baby."

"Okay."

Joan was a legal secretary, and we had worked together several times during the past year. I hadn't really pursued her previously, even though I had really wanted to. But we kept in touch between assignments, with weekly e-mails. So when I took the assignment, I e-mailed her. "Cool!"

Joan was originally from the Miami area and had been in northeast Ohio for five years. She and her husband had moved up so he could take a job with Alltell. Joan was a Florida girl, through and through, and wanted nothing more to get back to the Florida sun.

Anyway, on my first day, I got to work and went in. The hot receptionist sent me up to the fourth floor. I knew the attorney I'd be working for and where her office was. As soon as I got to her office, I saw Joan. Maybe this time I could introduce her to Mr. Happy.

She looked up at me.

"Hey! How are you doing?"

"Not bad."

"How long you here for?"

"Four months."

"Excellent."

"How's your husband?"

"Still breathing."

"What time you taking lunch?"

"1:00. Wanna come with me? McDonald's or something?"

"It's a date."

At that point Jen, the attorney, came out. She was cool. Columbia law school grad in her late 40's. Very, very hot. Untouchable, of course. But hot. Jen told me that I'd be working in the same office I worked last time and had set up an email account on Outlook for me. She had some depositions waiting for me, as well as some research assignments. She then went back to her office.

I loved Jen.

Great boss. She had a stressful job--no matter what you think of lawyers, they do work hard. And the next time you make a lawyer joke, ask yourself who you call for help when you or someone close to you is in legal trouble. Despite her hectic schedule, Jen never took it out on her employees, temp or otherwise.

Joan watched me watch Jenn leave. "Man, get your tongue back in your mouth." "Says the girl who just begged me to go to lunch with her."

One o'clock came fast and I went and got Joan and we headed to the elevator together. "I didn't beg you to go to lunch with me. But it's nice that you have your delusions to help you get through life."

"Please. You were so jealous when Jenn left I couldn't believe it."

"I. Wasn't. Jealous! You need to get a grip."

"Is that an invitation?" The elevator stopped and some people got on, so we shut up the rest of the way down.

We walked over to McDonald's and got our lunches.

"So, have you ever....you know?"

"You know, what?"

"Dipped your pen in the company ink?"

"A few times. Have you?"

"Yeah. Once before I got married.....and one time a couple of years ago."

"And you're bringing this up....because....?"

"Because I think you'd nail any girl you think is hot. Or try to."

"That a bad thing?"

"Mmmmm.....no.....but you like Jen. I can tell."

"Even if I DID hit on her, I wouldn't have a shot."

"Why not?"

"Jen's gay."

"No she isn't."

"Yes she is."

"Really?"

"Uh huh. When she leaves, go into her office and look at the picture of the brunette on the right side of her desk. That's her girlfriend."

"And I don't try to nail any girl I think is hot."

"Bullshit."

"Nice language. You kiss your mommy with that mouth?"

"Don't change the subject."

"Okay. I haven't hit on you. And I think you're beautiful."

"Shut up."

"Honest."

I think I embarrassed her.

"Uh, thanks."

"Wow. You sound like I called you a dog."

"No....just didn't think you looked at me that way. That was nice to hear."

"Are things going to be weird between us now?"

"No...not at all....just kind of took me by surprise."

"Good thing?"

"Yeah, yeah....it is."

"Well.....how about I throw something else at you?"

"What?"

"Why take two cars here? Want to car pool?"

"That'd be cool."

Joan lived just about 5 miles south of me, in Middleburg Heights.

We went back to the office and worked until our afternoon break, which we spent outside grabbing a smoke.

I told Joan I'd pick her up around 7 the next morning and we headed back into the elevator. We were alone, so I slipped my arm around her waist. She smiled and said, "Don't tempt me."

"I just have my arm around your waist. No big deal."

"Didn't say it was."

"So you can resist this, huh?"

"Uh huh."

"My ego's in tatters."

We got back to work and soon it was time to go. I went up to Joan, "You ready to go?" "Uh huh." Jen was long gone, so we headed out. The elevators were jammed. Joan looked at me and said, "Stairs?"

We got down a couple of flights when we got to a landing. Joan grabbed my arm, and said, "Come here," and wrapped her arms around me and kissed me. We really went at it for several minutes until we heard the door open at the second floor entrance. So we got going and walked over to the parking garage.

"What level you on?"

"First. You?"

"Second."

"You got any rubbers?"

"Yeah, in my van."

"Too busy here. Where can we go? A motel? Let's split the room."

"How about the Motel 6 in Strongsville?"

"Yeah....see you there, baby."

It was about 6:30 by the time I got to the bank in Strongsville. I took out sixty bucks at the ATM and drove to the motel. Joan was waiting for me in the parking lot. We went in and paid for the room and got the key.

Joan and I stripped fast and started kissing. I put her on the bed and started eating her wet pussy out. Her legs were spread nice and wide, and she was playing with her tits as I sucked and kissed her hard clit. Soon she let out a loud shriek and came. "Let me suck your cock."

"So.....we going to fool around or what?"

Joan got on her knees and wrapped her warm lips around my cock. After she sucked and licked my cock for a couple of minutes, I bent her over and she braced her hands on the mattress. I ripped open a condom and put it on my cock.

I shoved it in hard and fast and clamped my hands on her hips. She bucked back every time I thrust into her and soon she was groaning and begging me to fuck her fast and hard. I don't know how I held on as long as I did, but it was several minutes--and several Joan orgasms--later when I took one final plunge in, groaned as loudly as she did, and came.

We fell onto the bed, breathing hard.

"I told you that I thought you were hot."

"I wanted to fuck you the first time we met.....didn't have the guts.....wish I had...."

"I know we don't have much time, but I gotta fuck you again."

"Yeah..."

Joan pushed me down and sucked my cock until I was hard again. She rolled another condom on and straddled me and lowered her soaked pussy onto my cock. She let out another loud groan.

Joan rode me fast and hard as I played with her hard nipples. I'm surprised the bed didn't break. This was high-octaine fucking at its best. Finally, she came again and I filled up another condom. Joan stayed on me, and we just stared at each other, breathing hard and trying to catch our breath.

"I'll keep the key," she said.

"We can meet here before work, then check out."

"What time do you want me to pick you up?"

"Five thirty."

"I wanna fuck you twice."

"At least."

I picked Joan up the next morning and we drove straight back to the motel room. We spent an hour sucking and fucking and then grabbed a shower together and dried off and headed down to work.

We continued to see each other throughout our assignment and beyond. While we were still going into Cleveland, we'd play wherever we could. Quite a few times we'd drive into work early and play in the van. Whenever Alex was traveling, we'd go straight to my place and play, and then I'd drive her home.

It got quite a bit easier when we ended our assignment. I went back to freelancing for awhile and Joan started taking short-term assignments. We almost always met at my place, although we were able to get it on at her house a few times as well.

Up to the bedroom.

Joan ended up moving back to south Florida in September. Legal secretaries can get jobs anywhere, and she had had enough of her husband. I don't think he was a bad guy or anything. It was just that they weren't compatible. So they decided to split.

Joan moved back in with her parents and called me a week or so after she moved. She had already gotten another job and was planning on returning to college a few months later to finish up her bachelor's degree.

I got lucky and got a visit from Joan in 2004, when I was still in Tampa. She came up and spent a few days when Alex was on a business trip. Unfortunately, that might be the last time I get her into bed, as she got remarried 8 months ago.

She went back to Johnson and Wales University and earned her degree in management and now is the office manager for an engineering firm in Miami.

We still keep in touch.