Category Archives: My Sex Life
By Kendra Holliday | May 14, 2013 at 6:29 am
Have you ever had a close call during sex? We have had the following close calls (no coitus interruptus for us – the world is on pause until we CUM!)
- “They’re going to be here any minute!” I protest as he starts taking me in his bedroom. He ignores my silly plea and has his way with me, which includes fingering me until I’m flushed, quivering, and crying out with a climax. The front door opens, he kisses me, then leaves me to compose myself as he greets the guests. “Wash your hands!” I hiss.
- We order a pizza, and are waiting for it to arrive. He bulldozes me back to the bedroom, bends me over the bed and yanks up my skirt. I’ve learned not to wear panties around him. He unzips his jeans. He is ready. He pushes into me and fucks me hard. I hang on to the bed, thrilling at the intensity. The doorbell rings, he dumps his load in me, then tells me as I’m lying there panting, “You just relax.” He zips up his jeans and strolls to the door without missing a beat. I hear him lazily greet the pizza guy. He acts perfectly normal. I’m in a daze.
- We’re at a restaurant that’s attached to an office building. We order our food, then both head to the bathroom to wash up. I paw at him in the hallway, pretending I want him right then and there, but I’m just teasing. He’s not. He passes the bathrooms and pulls me over to the elevator. and punches the button. The door opens, he drags me in. He pushes me down on my knees as the doors slide shut, and unbuckles his jeans. He pulls out his already hard cock and puts me to work. I obediently blow him, it’s fast and furious, my head is spinning. After about three minutes, I wonder when he’s going to cut the party short and release me from my duty. All of a sudden, the elevator starts to move. Up. On the 2nd floor, he starts to cum in my mouth. On the 3rd floor, he finishes cumming in my mouth. At the 4th floor, I’m standing, swallowing, he puts his dick away, and the door opens. A woman is standing there. “Excuse me,” he says and brushes past her. I trail along behind him, disheveled and wiping my mouth.
As you can see, I have a hard time making the first move.
By Kendra Holliday | April 27, 2013 at 7:19 am
I’ve had my yoni eggs for almost a year now. I’ve had them since before my hysterectomy.
I’ve futzed around with them off and on over the months, not really committing to them, just experimenting.
(Before you read any further, make sure you read my post yesterday all about yoni eggs so you know what the hell I’m talking about.)
One night, I had an intense phone conversation with my partner Matthew. Hectic life was getting in the way of our relationship and we weren’t feeling connected. The talk left me feeling agitated and upset. Exhausted, I went to sleep feeling like a smelly, wrung out dishrag.
At 3:40, I woke to great thunder and lightning. The tumultuous storm rattled the windows. I fretted and tried relaxing.
I drank a glass of wine.
I stuck my tiger’s eye yoni egg inside me – I wanted something inside. It was soo cold going in.
I frantically masturbated. When I came, I screamed. Then I cried hard, and fell back asleep. I had weird dreams, but don’t really remember them.
I woke to the alarm feeling dreary and drab, not refreshed.
My body clenched the egg tight, it didn’t want to let it go. I had to push it out, and when I did, it was really hot, and some ejaculate came with it.
More tears – this time from my pussy. More release.
By Kendra Holliday | April 13, 2013 at 9:46 am
My date night this week was crazy intense.
Wednesday nights are Matthew and my sacred date nights. This means that as long as we’re both in town, we are together and enjoying life in some way. Sometimes we double date, or have a threesome, or foursome or moresome. Sometimes we’re hosting an event. We especially love when it’s just the two of us (it feels so rare!) so we can soak up some precious quality time. Our date themes range from dive bar crawls, movie nights, a fancy dinner, a BDSM scene, reviewing sex toys, to sitting on the couch in our comfy clothes eating ice cream and laughing our faces off.
And of course, sex. As much sex as possible. Sex helps us feel connected and close.
Last night, our top priority was booking our flight to Vienna. It’s been on our radar for months. Both of us have never been to Europe before, and we chose Vienna for our first city to visit. I heard it’s romantic, brilliant, amazing, the City of Music, the seat of power for many world empires.
We queued up Beethoven’s Fifth Symphony, then sat down in front of the laptop.
Initially, we had planned to enlist Beethoven’s Fifth for a BDSM scene (we’re celebrating each symphony in a special way, just do a search for “Beethoven” on this site and you can review). But fuck, booking a big trip is almost as intense as getting flogged blindfolded and shocked unexpectedly and having your face fucked.
By Kendra Holliday | April 9, 2013 at 6:38 am
Ed Note: Here is Matthew’s version of my post yesterday featuring a Professor/student threesome roleplay…
All the details are in place. The ladies are to be in skirts for easy access with no bras or panties when I arrive. I am the Professor. They are my students and roommates. I have seen them all semester in the back of my class giggling and smiling away. They ask me to stop by their house so they can ask me a few important things about their education. I oblige.
“So…what can I do for you ladies?” They dance around the subject for a bit. Playing with their hair and smiling at each other nervously.
They finally get around to telling me they are worried about their grades and are hoping for some extra credit to keep their scholarships.
I inform them that I don’t offer extra credit and that if they would have read the syllabus they would know that. They resort to pleading.
“You two seem like you absolutely NEED this.”
“Yes!!! We’ll do whatever you want!” they answer, almost simultaneously.
The ball is rolling in my head.
“Really?” I inquire coolly.
I start circling them. The blonde one won’t keep her back to me. The brunette lowers her head like a puppy whenever I close in on her.
“I think there is something I can do here, but on one condition. You absolutely MUST keep this a secret.”
“Oh yes. We can keep a secret!!!”
I continue circling them. Stop near each of them alternately to graze their hair, inspect their waistlines or smell their necks from behind.
They confirm my suspicion that they are “really close friends” as they start kissing after I tell them to prove their “closeness”.
By Kendra Holliday | April 7, 2013 at 7:13 pm
Ed Note: This is the post that was front and center when my former boss discovered my site in 2010 and fired me for having a sex blog. Um, yeah.
Matthew, Rockabilly Girl and I were up for some Professor/student roleplay.
He told us to wear skirts with no panties or bra. The air was charged with sexual tension, but he didn’t make his move, not yet. He informed us, “The game begins when a glass of whiskey is set in front of me.”
I eagerly fetched him a glass, and with the clunk of the drink on the table, a switch was flipped.
Rockabilly Girl and I stood nervously grinning as he took a swallow of Dr. Jeckyl/Mr. Hyde potion, set it down, then loomed over us.
He was the Professor, and we were his students.
“So, you two want an A, do you?”
We looked at each other and giggled, but he was dead serious.
“Yes, please Professor, we don’t want to lose our scholarships,” we said earnestly.
“You two are roommates?” he asked.
“You don’t LOOK like best friends. Prove it.”
We giggled and tentatively faced each other. Then we started making out, sighing and getting into it.
He circled us, leaned it to sniff us, stood very close.
By Matthew | April 3, 2013 at 6:43 am
Ed Note: What is it like when your partner tells you she wants a gang bang? What’s it like organizing one? How does it feel watching your loved one get worked over by a bunch of men? Here is my partner Matthew’s perspective of the gang bang celebration…
I’ll be honest, as always. Gang Bangs aren’t at the top of my turn on list…at least they weren’t.
I’ve seen some pretty hardcore, BDSM-related videos. I was witness to somewhat of a gang bang in high school. It was more “Running a Train,” actually. I remember sitting on a couch in one of my classmate’s houses. Upper class men took turns going to the backroom to have sex with a girl from a neighboring town.
At one point, one of them tapped me on the shoulder as he was walking by, adjusting his belt, having just emerged from the frequented room, saying, “You’re up!”.
I politely declined. It creeped me out. I felt like the girl had been coerced into doing it. NOT COOL! Even for me at that age, when I was known for how much head I received from varying teenage “sluts”, it was a hard limit.
Flash forward to me know. I am a much different person. A feminist. A father. A man. The term “Gang Bang” has some negative connotations for a lot of people, including me, thanks to the massive money making misogynist marketing of the porn industry.
So, when Kendra and I were talking about how to celebrate her 40th birthday and she mentioned the idea of having a gang bang, I was slightly, and briefly, wide eyed. We mulled it over a bit. I really do enjoy watching her get pleased, be pleased and give pleasure. Why not a gang bang? With the right group of guys, organized in the right way, it could be awesome.
AND IT WAS!
By Kendra Holliday | April 2, 2013 at 7:47 am
Yesterday I posted my epic gang bang recap. Today, you get to read some of the perspectives of the eight men who participated! They were all so handsome, sexy, giving, and talented!
I’m still processing the whole evening. I think the part that I find the most interesting is how comfortable the whole thing felt. I know that has so much to do with the people that were chosen to participate. Even though I didn’t really know anyone else other than having had some casual conversations with a few of them in the past, there was an almost instant comfort with everyone there. It was interesting how polite everyone was throughout the entire evening. Not only was it apparent that everyone there respected Kendra, we also respected each other.
It was not only a “bucket list” kind of activity, it was also a learning and growing experience for me. I found out that I’m comfortable being naked around people I barely know. I thought I would be, but to have it confirmed was good. It was a self-esteem and self image boost not only to be invited to participate, but to find that I was not intimidated and felt like I was able to “hold my own” with people who were more experienced than myself.
A Romantic Gang Bang
I would like to express my deep thanks and appreciation to you for allowing me to be part of Kendra’s Birthday Gang Bang. It was superbly organized and executed. Your efforts have proven that a gang bang, crude almost by definition, can also be an affair that is classy, civilized and elegant.
By Kendra Holliday | April 1, 2013 at 3:16 am
Would you be nervous if you knew eight men were on their way over to fuck you all at once?
Would you be nervous if you were a man driving to a gang bang event, having never met some of the other guys, and this being a new experience for you?
Think about it for a minute.
I mean, gang bangs seem like a hot idea in fantasy, but how do they translate in reality?
Well, when you plan it right, they translate really fucking well.
Truth be told, I wasn’t nervous. I was excited. I was radiant.
Now, if I was about to do public speaking, I’d be nervous. If I was about to parallel park a car, I’d be nervous. If I was about to walk into a rich country club, I’d be nervous.
But this was natural for me, even though it was my first time trying such a thing. As you all well know, sexual acts are where I shine.
Here is me right before the guests arrived:
See? I’m making the OK sign.
I dressed up because all the guests were coming in suit and tie. Classy!
By Kendra Holliday | March 25, 2013 at 2:25 pm
This weekend I celebrated my 40th birthday with a gang bang!
It was incredibly amazing, and I can’t wait to share the details with you! But first I need to clear any images or writings with the attendees in order to ensure their privacy, so bear with me as I take the proper steps.
In the meantime, let me share with you the fun pre-party planning.
I bought a tiny, elegant bottle of St. Germain for my house madam, Bianca. She took care of the front of house – serving drinks, fetching towels, conversing with men who were taking a break. She was incredibly elegant in a custom made gold and black corset and stockings, complete with a little French chapeau.
I bought a can of Vienna Sausages for Sissy Maid, who took care of the bedroom duties – condom clean up, towels, offering me water and the men lube. He has a small penis humiliation fetish.
I got a pack of Red Bull for David Wraith, my gang bang referee and photographer extraordinaire!
Here are some other party favors.
I got a superhero ball-n-paddle for those waiting in line. OR maybe they could use it on me!
By Kendra Holliday | March 24, 2013 at 8:39 pm
Thank you to David Wraith for playing referee / photographer at my 40th birthday gang bang! Here is one pic he took…
More amazing, incredible, fantastic, hilarious details coming soon!
OH and if your tie is hanging in my collection, you know who you are, and you are awesome.
By Kendra Holliday | March 21, 2013 at 11:59 am
My birthday gang bang happens this weekend!
Everyone who is involved is so excited. They’ve been having weird dreams about it. They’ve been freaking out with nervous excitement.
They ask if I’m nervous. Not really, but I get giddy every time I think about it!
I have to admit, organizing it has been like planning a wedding for my partner and me – it’s been stressful, but in a good way. Almost everything seems to be going as planned, which is amazing. It looks like every man we invited will be coming. Sissy Maid has been watching lots of close up cum shots on XHamster in order to gear up for his special role.
So many women have written me privately to express their jealousy. All the men involved have taken the event as an opportunity to get tested for STIs. My clean bill of health report is sitting on the counter and ready to show my guests.
ANOTHER one of my gang bang dudes sent me this pic as a teaser:
Here is the first one:
I can’t wait to drape those ties on my dirty, naked body. And toast my stable of studs!
One of my sweet girl friends from grade school asked me if I was doing anything special for my 40th birthday. When I told her, she primly choked out, “Well that is… neat-o.”
Not the way I would describe it – I was thinking more along the lines of EPIC. But we’ll see.
I think it will be my BEST BIRTHDAY EVER.
And hey, ladies – I’ll give this crew a test drive, and if all goes well, maybe they can help you out with YOUR gang bang fantasy. Have cocks, will travel!
By Kendra Holliday | February 27, 2013 at 9:34 pm
Thanks to a business trip this week, I get to indulge in my cuckqueaning fetish.
Normally when I think of out-of-town trips, I ponder the possibility of having sex with someone new – a hookup.
This time, I wasn’t into that. In fact, I was feeling the reverse. I was a little peeved about having to leave town, so I stumbled across an idea while packing.
I was acting like a whiny kid and having a hell of a time packing, and my partner Matthew was helping. He asked me, “What do you want to bring besides your vibe?”
I flippantly told him, “Actually, I was thinking about not taking anything with me and just forgoing orgasms for a few days.” Usually I get off at least twice a day, so that’s unusual for me.
He leveled a stern gaze at me and said, “Be careful what you say, because if you decide on that, I’m going to make you stick to it.”
OY was I sure? I thought hard on it. It had been a while since we played around with orgasm restriction. There was one time when I went to California and ended up fucking a hot artist, but since I wasn’t allowed to cum, I had to hold really still and just let him use me to get off. That was pretty hot.
“OK,” I agreed. Then I had another idea. “Can you fuck someone while I’m gone?”
He smiled. “I’m sure I could work something out.”
“So I’m not allowed to cum at all, but you’re allowed to fuck and cum all you want?”
My pussy twitched!
By Kendra Holliday | February 24, 2013 at 7:15 am
A while ago I announced I was going to try DP for the first time.
We scheduled it for a laid back Saturday afternoon.
Our friend Homer helped us fulfill our fantasy. Homer is a total sweetheart, we both like him a lot – he’s the perfect choice for this intimate experiment.
That morning, I woke up hornier than usual. I got off twice, once with the vibe, and once with oral. Matthew was so attentive and supportive. I’m so grateful to be in a relationship where we can make our wildest fantasies come true!
We worked him up a few times as well – sucking him, jerking him off in the shower, taking him right to the edge of orgasm, and then backing off.
Mid-morning, I felt pretty nervous and had an upset stomach. I don’t know about you, but it’s not always easy to plan anal – it’s something I have to be in the right mood for, physically and mentally. I didn’t want to miss this golden opportunity, so I fasted to keep my system clear.
I ran to the drugstore to get an enema. I bought a bunch of stuff so that the enema would blend in with my purchases, but when I got to my car with my saline solution, body lotion, mineral water, and eyebrow brush, I realized I FORGOT to get the enema, so I had to go back inside and buy it solo.
Me = anal dork
The woman checking me out said, “Have a good one!”
God I hope so.
Back home, I holed myself up in the bathroom and gave myself an enema. Usually it only takes one round to get the job done, but today I did it three times just to be sure. Eek, Homer was going to show up any minute now!
I went with a relaxed, playful look for our encounter, wearing a little crocheted peasant cover that offered easy access:
I was sooo giddy! I kept jumping up and down and giggling:
By Kendra Holliday | February 19, 2013 at 5:42 pm
One of my goals in life was to publish a book by the time I turned 40.
I never got around to doing that (at least there’s the Show Me anthology!), so I’m having a gang bang instead.
Someone asked me: “What’s the best way to call slut-shamers out on their bullshit and make them feel like total asses for being total asses?”
I replied: “By being sluts who are totally happy, healthy, and well-adjusted? By not inviting them to my gang bang?”
That’s right – there are NO slut-shamers attending my gang bang.
The eight or so men attending are friends of ours, and fabulously open-minded and sex-positive. And you know what? SO ARE THEIR PARTNERS. I want to thank their wonderful partners for giving their blessing for their men to be a part of something so extraordinary. THANK YOU FOR SHARING!
Everyone has different fantasies when it comes to gang bangs. One woman I know said she had one where she was blindfolded and her husband found five black men and five white men from Adult Friend Finder to come work her over. My friend Jade went with an abduction surprise scene.
I’ve been watching a lot of gang bang porn. This one featuring a British woman and ten men freaks me out. As in, I watched it and I was worried I’d have bad dreams afterward. I’m not ready for that hardcore scene.
This one featuring a woman in a darkened theater is more up my alley. It’s more natural, less humiliating. To me, dirty talk is not humiliating, it’s just sexy.
Celebrity Love Coach JuJuMama doesn’t care for the term “gang bang;” she prefers “feminine magnetism exercise.” I can dig it.
My partner Matthew is managing my gang bang. Here is the letter he wrote to our Chosen Few, our minyan, if you will:
By Kendra Holliday | February 8, 2013 at 6:31 am
Note: I first published this on Jan 7. My first DP is tomorrow. I am in no way any more prepared for this than I was a month ago. Wish me luck!!!
DP = Double Penetration.
Now that I’ve had a few great Male-Female-Male (MFM) threesomes, I’m ready to take it to the next level and try a real, live cock in my pussy AND a real, live cock in my ass AT THE SAME TIME!
You know – LIKE IN PORN.
I can’t ever tell if any of the participants are enjoying it or not, because they’re all concentrating so hard. It looks like a lot of work! But is it intensely hot? Anal can be. MFM’s can be. So why not combine them all together? (Wouldn’t you love to see DP outtakes?)
I guess I should practice with these toys first. I haven’t had anal sex in a few months.
The two men are 250 lbs and 300 lbs – I’ll be 130 lbs of women between them. A thin wall will be the only thing separating the two. I’ll bet their balls will touch. In my eyes, it’s almost like being right in the middle of GAY PORN! But there’s a woman in the center of it all, so it’s NOT!
I’ll be in the middle of a bull pen, a shark tank, a bear pit! Grrrr!
Naturally we needed to find the right guy, someone we both like a lot. I mean, I plan on facing him as we do it. The guy is Homer, aka the Gentleman from this date I had.
I’m trying to figure out the best position – I’m thinking Homer should lie on his back toward the end of the bed. I’ll be on top, and Matthew will bring up the rear.