Author: OGLifeguardOne

The Study Break: Not [M]y [F]irst Time

In college, I had a good friend with whom I had an on-and-off relationship. She was smart, beautiful, and way out of my league. She had an off-campus apartment, which helped in facilitating our purely sexual relationship. Our encounters took the form of “study breaks,” and they never lasted more than an hour or so. Let’s call her Meg.

One night, while writing a paper in my dorm room, the guy across the hall knocked.

“Call for you. Don’t be long, I need to phone my parents.”

I grumbled something, nodded, and picked up the phone.

“Hi.”

“Would you mind grabbing a cheese pizza and some soda? Come over to my apartment in about an hour? I have an exam tomorrow and I need a study break.”

“Yes ma’am.”

I ordered, picked up, and arrived on schedule. She took the pie and carried it to the kitchen, where I noticed the table was covered in books, binders, and notes.

“I’m so hungry,” she said, retrieving a slice from the box. Even when she was studying she was hot. She was wearing running shorts, a sports bra, and socks. Her dark hair was pulled back in a ponytail. Read more »

[M]y [F]irst Time: In a Bar

It was the end of what I thought would be a fairly typical business trip. Except, it wasn’t typical at all.

On the last day of meetings, I learned that the promising start-up was not starting up at all. In fact, the company was broke. The only bright spot was that I had been given a stack of cash to cover my travel expenses and my last three days of work.

I did the only thing that made any sense. I checked out of my hotel and grabbed a cab. En route to the airport, I noticed a dive bar with a sandwich board out front that proclaimed a $2.00 SHOT AND A BEER.

“Cabbie, can you drop me there?” pointing to the bar.

It was a little before noon, and my flight was scheduled for 6:00pm. I had time to kill, and some cash to help things along.

I was not going to mope at the airport, I was going to mope properly, in a dive bar, whacking back $2.00 shots of cheap whiskey chased by cheap ass beer. Read more »

[M]y [F]irst Time: Detroit Hockey

I met her in early January at a nightclub in Miami. We were drinking, dancing, and making merry. She was wholesomely cute, in a midwestern sort of way. She played softball at a college in Michigan, and had come to Florida to visit her grandparents before returning to school. I was home for the holidays, and was mainly looking to blow off some steam.

About 1:00am, she told me that she was leaving because her brother wanted to get back to their grandparents’ home. “I mean, unless you want to give me a ride.”

“Sure,” I said.

Another hour passes, and she tells me that she is ready to go home. We decamp, go to my car, and start driving. I ask her for the address, and she gives me the street number. 

“What’s the address again?”

She repeats it.

Fuck! That’s right down the street from my house.

“Do you know how to get there?”

“I think so,” I said.

30 minutes later, we arrived and I walked her to the door.

“Do you want to come in? I’m pretty sure everyone is asleep, and I have my own room.” Read more »

[M]y [F]irst Time: The Much Older Woman

I was 21 when I met Barbara at a bar in Miami. I didn’t so much notice her as she noticed me.

She was a Canadian, in her late 50s, married, a little overweight, a lot tipsy, and seemingly one of those snow birds that Floridians despise. I learned that her husband played golf every afternoon before meeting her at the bar where they would have cocktails, and dinner. Once a week, they’d have sex.

Okay, maybe a little too much information for someone you’ve just met, but whatever floats your boat. I sometimes over-share when I’m drunk, so no biggie. 

Another drink later, her husband shows up, she throws a twenty on the bar and says goodbye. As she stands up, I check out her lips, smile, and breasts. As she walks away, I survey her nicely tanned legs, matronly ass, and graying hair. Not bad, Barbara. Not bad. 

Fast forward two weeks, and I am once more at that same bar.

“I was hoping I’d see you again.” She kissed me on the cheek. She smelled amazing. And, for the first time in my young life, I was sexually attracted to a much older woman. Read more »

[M]y [F]irst Time (Part Deux)

The bed side light was on, and I found myself between my naked wife’s legs (after a one year separation).

“Show me how you would have cleaned your little slut’s cunt,” she purred.

I looked at her pussy, newly shorn, lips puffy and engorged, cum dripping onto the sheets of the guest bed where, until just a few hours ago, I had been sleeping alone. 

It felt wrong talking about the woman with whom I had cheated; but, my wife goaded me into it. When she learned that my “little slut” didn’t like receiving oral sex, she knew she had me.

She grabbed my hair in her hands and said, angrily, “Show me.”

As she pushed my head between her legs, she raised her smooth pussy to my mouth, and I was left with little choice but to lick, nibble, and suck her pussy. I could taste my cum, along with her sweet pussy. I dragged my tongue across her lips, and her clit. I parted them, and dipped inside of her. At that moment in time, I lived for her pussy, and her pussy repaid the favor, spasming with pleasure as the fourth (or fifth?) orgasm tore through her body. Read more »

[M]y [F]irst Time

After being separated for nearly a year, we got back together.

My wife told me that it was going to take some time before she’d let me back in our bed, and I understood why. She was still struggling with the fact that I had cheated on her, but my moving home was a start.

I slept in our guest room, and I was on my best behavior. I had resigned myself to the fact that it was going to be a long, cold, lonely winter.

Then, one night, I heard the door open and close.

“You’re not coming to stab me, are you?”

She didn’t say anything. She just slid into bed beside me.

She dragged her nails across my chest, and down toward my stomach.

She whispered in my ear, “What was she like?”

I told her I didn’t want to talk about it.

She grabbed my cock and said, “Tell me.”

I was getting hard, and I was tired. I gave in.

“She didn’t like to be on top. She liked me behind her, or on top of her. She liked to suck my cock and swallow my load. She hated being eaten out. She….” Read more »

[M]y [F]irst Time

I was 41, and separated from my wife. I was behaving (mostly), and working on trying to save our marriage. I had my own place, and we had a pretty good arrangement. Things were looking up, to be honest; and, we had talked about getting back together.

One evening, while I was sitting in my living room, the bell rang. I went to the door, and was greeted by a former colleague who lived nearby.

“Are you divorced yet?”

“No.”

“Well, I brought you a bottle of wine. Invite me in for a glass?”

“Sure?”

Amanda was 50, blonde, petite, and in excellent shape. She had small breasts, a flat stomach, and awesome legs. What could go wrong?

She sat down in the living room while I opened the wine, and poured two glasses.

“You know,” she said, “we’ve never been available to each other. We still aren’t.”

Okay, that makes this all a lot easier.

We start talking, and we have another glass of wine.

And another.

The bottle she brought is empty, and she says she should get going. Read more »

[M]y [F]irst Time

I had been interviewing for a receptionist/assistant at my business. I collected about a dozen resumes, interviewed three or four women, and had settled on a woman who had been a temp the previous year. Then, a past intern called me and said that she’d heard I was looking for someone, and that her mom’s best friend had been laid off from her job the week before.

I told her that I would talk to the friend if she could stop by that afternoon.

Around 4:00pm, this somewhat disheveled woman shows up, apologizing because she had to get her kids from school and take them to work. She was married, 45, curvy, and wearing a skirt that was way to short for an interview. She looked like a normal, everyday mom. I offered her coffee, and when she took the cup, I noticed three things.

She had a great smile, very nice breasts, and really toned legs.

She sat across from me, and immediately tugged on the hem of her skirt, which had ridden up a little. She apologized for being late, and as we talked (and she relaxed), she demonstrated that she was right for the job. She was quick, could type, and was organized. Read more »

[M]y [F]irst Time: The Series

During my senior year of college, I started to hit my stride.

After the forgettable experience during which I lost my virginity, I kept trying. (Gotta get back on the bike if you fall off, right?) I gained confidence, and eventually, I got better.

Since I couldn’t get a do-over, I decided to think of subsequent experiences as “My First Time….”

I had taken a trip to see my former HS girlfriend, who went to another college. We weren’t really sure where we were in our relationship; but we were most definitely friends, leaning towards trying to make a long-distance relationship work.

I had been to her school for a few days, and was flying back to my school, which was several states away. At this point, it bears mentioning that occasionally, flights would leave with one or two passengers, along with the flight crew. It was an early morning flight, and this was one of those times.

I got on the plane, and was told that I could sit anywhere. I selected a seat, and settled in for the flight. To be honest, I wanted to sleep, and I had just started to doze off when… Read more »

[M]y [F]irst Time

The Summer between my junior and senior years of college was going about like I expected. I was taking a class at the local university, working as a lifeguard, and racing sailboats in my free time.

At some point, my parents had a dinner party, and I started talking to the daughter of one of my mother’s friends. I was 20, she was 28. I was a dumbass, and she had a “serious boyfriend” (according to everyone). We hit it off, and I asked if she’d like to go out for drinks.

And, while she didn’t seem interested, she didn’t say no.

A few days later, she called and told me that she would pick me up at my house after she got off work. I was dressed in lifeguard chic, ready to go to the local bar, when she rang the bell.

She was wearing a navy skirt, a white blouse, and pantyhose. (I know, odd for the Summer, but she worked in an office.) I told her I wanted to change into something a little more dressy since she looked so nice. When she walked into my closet, she saw my ties and said something about how useful they could be. As we were flirting pretty heavily at this point, I made some comment about her tying me to the bed and having her way with me. Read more »