Category Archives: 8. Pre-DD stories

73. Pube Shaving Party

shave

Okay, so this image doesn’t really go with the title, but I thought it was cute.

I previously shared my Strip Quarters story as Mike suggested I share some of my sexcapades of my youth.  Here’s another fun experience I had in my college days/daze.

In the Strip Quarters story I shared my experienced with my childhood best friend, Amy.  Amy and I also roomed together in college.  It was my junior year, so about 1990 or so.  We shared a two bedroom apartment with two other girls, so Amy and I shared a bedroom while our other roommates, Cheryl and Barbara shared the other.

We all had boyfriends and while Amy and I still messed around at times, our roommates had no idea that we were bisexual – although at the time I didn’t think of myself as bisexual though.  I liked having sex with Amy, not women in general.   Anyway, suffice to say acceptance of this in 1990 was not what it is today, and Amy and I didn’t want it to be well known that we had sex with each other.   Barbara and Cheryl were great roommates but we didn’t hang around the same crowds and they were definitely more conservative and religious – especially Barbara.

There was a weekend where Barbara had gone back home to visit so it was just us three gals.  Cheryl had gone out with her boyfriend, and Amy and I just stayed decided to have a night in with just the two of us.  Amy and I were on the couch and started messing around, and Cheryl happens to come in as we forgot to lock the door and were not expecting her so early.   I don’t exactly recall but I think Amy had her hands down my pants which were unbuttoned, and I had a hand up her shirt.  Whatever the position we were in, there was no casually moving away and hoping Cheryl didn’t suspect what we were doing.  It was very obvious.

We looked up and Cheryl stood there for a bit and said something nervously like, “Uh, hey, hi guys.  Um, I’ll just leave now.” And she walked out.

Amy and I looked at each other with this look that was a combination of horror and humor.  We started talking about how to concoct some story to minimize the chance Cheryl would be freaked out.  We didn’t want her blabbing to everyone, and knowing Barbara, we felt she would completely freak if Cheryl told her.  We couldn’t come up with any great plan and just figured, “oh well, we’ll just tell her we were drinking and it was just a one-time thing.”

About an hour or so later Cheryl comes back and she is holding a bag.  She looked sheepishly at the two of us and said, “Okay, I want in.”   At the same time Amy and I said, “In on what?”

Cheryl was pretty nervous and said, “You know, I want to be with you all, in that way.”  Neither Amy or I could come up with any words to say as we were perplexed.  Amy opened the bag and pulled out a bottle of tequila and a porno.  Amy apparently went to the liquor store and an adult video store.  Amy said, “Look, I know I have been attracted to girls for a long time and tried to resist, but after seeing you two and after the night I had with my boyfriend, I just can’t hide it any longer.  I don’t know if you all think of me in that way, but I thought if we relaxed and had a bit to drink, and watched this movie, we could, you know, get in the mood?”

Both Amy and I took on the role of more consoling Cheryl than anything else.  It was clear she was nervous and uneasy.  I remember that despite her nerves, she still came across very sure of herself and her feelings.  She just poured her heart out to Amy and I, relived to get it all out to someone for the first time in her life.    The three of us talked for quite a while.  It became clear to us that Cheryl was a lesbian but had been suppressing it her whole life.  Amy and I ended up sharing with Cheryl everything about our relationship together.  Cheryl even shared that she had kissed Barbara once, very deeply and basically a pretty major make out session, but it didn’t go further.  It was alcohol induced and the next day Barbara told her she never wanted to talk about it and that it would never happen again and that was the extent of it.

Cheryl shared the many crushes she had on various girls and women throughout her life and that she knew she was different from a very young age, but worked hard to suppress it – and she was tired of it.  She said she broke up with her boyfriend that evening, and when she left the apartment after seeing Amy and I messing around the couch, she decided that was it, she was “declaring her major” as she laughingly put it.  She was attracted to women and she was done with men.

We proceeded to crack open the tequila and pop in the VHS.  We told her we didn’t need the video, but what the heck, let’s see what she got.  We talked over most of the flick, and as the booze took effect started to get playful with each other.  At some point all three of us were naked and having sex while the movie played in the background.   Occasionally one of us would glance at the tv and say, “Ha, look at that!”  We’d watch for a minute and then get back to the real life action we had going on in the room.

Towards the end of the movie there was a scene where this woman shaved this other woman and it too got our attention and we all commented on it.  Remember, this was 1990, ahead of the trend to go bare down there.  Anyway, I don’t recall if all three of us had orgasms but Cheryl definitely did.  We were relaxing in silence in a naked three-way embrace as the VHS had long ended.  Cheryl then said, “hey, why don’t you guys shave me?”

We were half a bottle in to the tequila and probably shouldn’t be trusted with a razor, but, we were game.  We found some scissors and the three of us went into the bathroom.    Amy had the honors while I directed, “Clip some more off here, clip some more off there.”   Once she was clipped down pretty short, Amy whipped out some shaving cream.  We got a towel and a bowl of water and Cheryl sat way down on her bed so her trimmed snatch was easily accessible.   Amy proceeded to lather Cheryl up and started shaving.  Amy and I took turns at shaving Cheryl and eventually she was bare.  It was quite a mess, as there was water, shaving cream, and hair everywhere.

Amy then said, “Who’s next?”   There was a “no thank you” from me, but Amy was eager and willing.  When we finished shaving Amy the two of them were both begging me to join the “bare down there” club.  Eventually I was talked into a close trim with the scissors, but no shave.

When we were all done we started back up messing around, and basically had sex the rest of night until we fell asleep.   When we woke the next morning we saw the mess we had left.  In our tequila-altered state we obviously had not been focused on keeping things tidy.   Somehow we had a trail of shaving cream and pubic hair all over the floor from the bathroom to Cheryl’s bed, even all over her bed.  We frantically cleaned up, washed the towels and vacuumed as we didn’t know when Barbara would be home.  We kept finding more hair and would have to pull the vacuum back out.  It was quite comical.

We never informed Barbara of what went on.  Cheryl was indeed lesbian.  She started dating other women.  Barbara was a year ahead of us and while she was not happy with Cheryl’s coming out, she continued to room with us the rest of the year when she then graduated and moved out. We heard the phrase “hate the sin, love the sinner” quite a bit that semester.

Anyway, Cheryl now has a longtime girlfriend and I hear they are planning to get married soon.   I feel good that I had some part to play in her coming out and start her on her journey towards accepting that part of her.    All thanks to a her walking in on us, the tequila confidence booster, and the resulting impromptu Pube Shaving Party.

Next: 74. Interview with Sir

64. Strip Quarters

Quarters

I am writing this post under a bit of duress.  Mike suggested I write about some of my sexploits from my youth.  It isn’t that I mind sharing – I am pretty much an open book.  But, I no more want to blog about what I had for dinner, (pork chops, sauerkraut, and mashed potatoes), give reviews of the last movie I watched (Citizen X, meh!), talk politics and religion (uh, no and no), than I want to share the amazing sexual adventures of a young and energetic Jenny.

I wanted to keep my blog focused on our DD journey.  However, there are only so many DD-happenings in a week that perhaps it can get mundane.   Spanking for this, spanking for that, blah, blah blah.  So, under the threat of tremendous punishment and public humiliation, I shall write about one of the stories Mike mentioned.

Okay – I hope you all got the light-heartedness of my tone.  If not, re-read the last few sentences with a sarcastic tone.  In all seriousness, while not my preference, I have no problem sharing such things.  It didn’t take any threats, it simply took Mike asking me to share this.  Yes, Sir!  Such is the life of a submissive!

Strip Quarters
This is a variation of the Quarters drinking game.  The difference is that along with taking a drink, you also had to remove one article of clothing.

To keep this adult oriented, let’s just say I was 18.  It is possible I was a year younger than that, but that’s for me to know and you to only assume if it makes the story hotter for you.  Plus, if you aren’t concerned with  minor factual details, again, let’s just say I was 18 already.

Amy and I both had boyfriends (mine was not Mike at the time, oh, and neither was Amy’s, as Mike conveniently didn’t mention, he also dated Amy at one time, but not at this time).  One of the guy’s parents was out of town so of course, it was party time for the four of us.  The guys had already been drinking before we started playing Quarters.

We start the game and eventually Amy and I were even with just our shoes, socks, and shirts off.  So we were in our pants, panties, and bra.  The guys were naked.  Their nakedness was not new to us as on a few occasions we have had sex in the same room….my boyfriend with me, and Amy’s with her, and on a few occasions we’ve watched each other give head to our respective boyfriends.   With the guys effectively out of the game, they wanted Amy and me to continue.  We did, and I lost my bra and pants, but still had my panties on, and Amy was now topless and down to her pants and panties.  We look over and the guys are passed out.

We discuss whether or not we should finish, and since neither of us were big drinkers we figured we’d had enough and would stop.  We tried to arouse our boyfriends but they were out cold, and frankly, the thoughts of sex with them didn’t appeal to either of us as they would probably not get it up, pass out on top of us, or worse, piss and puke on us.  Okay, let’s reset the mood after that buzz kill of a visual.  Remember, both of us are topless.  Two topless young women.  Let’s proceed.

Amy and I are slightly buzzed, a bit aroused, and our guys are laying naked and out like a light.  It was a funny moment as we looked around the room, looked back at each other, looked over at the guys, and then looked back at each other.  It was like we both instantly thought of the same thing and simultaneously got up from our seats and lunged towards each other into a deep kiss and embrace.

We ended up on the floor and completely forgot that the guys were in the room until we had brought each other to orgasm through manual and oral means.  When we were done we looked over and the guys hadn’t budged.   They would have so freaked out if they woke up as Amy and I had never shared our secret with anyone.  I think we would have freaked out as well.   We joked afterwards that if they did wake up we would have just denied it and said it was obviously a drunken dream.

So, that’s the strip quarters story.   Amy and I having sex in front of our passed out boyfriends who, to this day, don’t know they missed out on a show.

Note from Mike:   Okay, yes, I dated Amy in high school.  I wasn’t hiding that, it just wasn’t pertinent to my last note.  I only dated Amy so I could hang around Jenny more while she dated these hideous jerks (better known as my friends).  Okay, not all were jerks and not all were my friends.  Oh, and it also helped that Amy had nicer tits.  Ha! That’s a joke.  As in, that is a fact, but it was intended to be funny.  Hey, to be fair, apparently one of these guys had quite a large cock, so Jen tells me.  No shame in that.  Amy had nicer tits than Jen and Jen’s boyfriend at the time had a bigger cock than mine.  It is just the facts.  

If you wonder how I feel about these stories, the answer is they are a part of her history and I enjoy knowing all her history.  That history has no bearing on our love for each other in the present, no more than my history does – although admittedly mine is a bit duller.   Jen’s quarters story is one of my favorites because it really captures her openness and the casualness at which she approaches every adventure.  No worries, no stress, no regrets, no judgement.  Just in-the-moment fun.  That’s something she slowly got away from until DD entered our lives.   She now once again is living in the now, is fully present now, and not giving up a piece of the now for some elusive promise of the future.   Just like she says in her post, I Found my Thrill.

Next: 65.  Full Body Flog

 

62. Sexual Adventures of Pre-DD Jenny

Feel
Mike gave me the suggestion (or is that an order?) to write about my sexual experiences in my younger daze, um, I mean days.   I might as well start from the beginning, way back to my virgin days.   Yes, hard to imagine, but I was once a virgin.

I joke that by the time I had sex with a guy (at age 17) I was a very experienced virgin.  By the time the “magic moment” arrived I was well versed in mutual manual and oral stimulation – both with guys and yes, with girls (actually, girl, as in singular).   My first sexual experience was in 1984, before it was an in-thing to be bisexual / lesbian.  Not to say it is always accepted today, but it was not talked about back then and definitely not something you wanted people to know about.

I’ve know my best friend for life, Amy, since kindergarten.  She lived just a few blocks away and we were extremely close.  So fast forward to when we were 15.  We had seen each other naked countless times so it wasn’t even a thing.  Amy had a swimming pool in her backyard and it was pretty secluded, so one of us, not sure which, got the idea to skinny dip.  We would get freaked out every time we heard a noise that sounded like a car pulling up or a car door closing.  We would run and grab our suits and then laugh when no one was there, then get naked again.

One day we were finished with a swim and we were in her bathroom drying our hair.  We both had shorts on but no tops.  I commented about her breasts, which I’ve done before, regarding her abundance and my lack thereof (she developed quite early and rapidly).   She made some comment about me being obsessed with her tits because I always stared at them and talked about them.  Guilty as charged!  I said something about them looking so squeezable or something like that and she said something like, “Well, give them a squeeze and see.”   It wasn’t a sexual thing, it was just playful and innocent, or at least seemed that way.   Well, apparently I groped her for several minutes in a trance like state.  We were real quiet while I squeezed and gave her a major feel up.  Her nipples got big and when she noticed it she broke the trance by covering her tits with her arms and moving my hand away and saying “enough!”  We then both just laughed and I said something like, “Yep, they are squeezable.”  That was that.  Nothing more to it.

It wasn’t much longer after that day that Amy and I were talking about masturbation.  That was a common topic for us as we would tell each other about our favorite things to hump and pretend.  She told me that ever since I “felt her up” (as she referred to it), she realized how good it felt to play her nipples.  I was quasi-offended at her statement that I “felt her up” and part-joking/part-serious said that “I did not feel you up! I was just curious!”  Amy then said something like, “Well, I am curious too.  Can I feel yours?”   So, I let her.  It wasn’t long before we both had our hands in each other’s shirt.  This curiosity turned sexual.

Without going into all the details, the curiosity that we satisfied that day with a mutual grope session turned into greater curiosity and greater satisfaction on subsequent days and weeks.  While we took it slow, it eventually led to us exploring many facets of lesbian sex.  Neither of us felt bad about it.  We both liked boys (a lot) and both felt like we weren’t “having sex with another girl.”  We were just having sex with each other.  It was nice that we never attached anything negative to what we did.  I think that healthy beginning, added to my zero sense of shame, set the stage for a positive outlook on all things sex and my sexuality.

I’ve got a lot of Amy sex stories, not all involving just her and I messing around.  We also roomed together in college.  I could fill several posts with our many adventures. Perhaps another time, and I’ll stick to the stories that occurred at age 18+.   It’s kinda’ creepy thinking about who might be getting aroused by stories of my early pubescent romps (yes, I am talking to you, you sick f*ck!).   Just kidding.

A word from Mike:   Hello all, not sure what to add, but Jen asked that I occasionally share my reaction to a post.  Not much for me to react to as these stories are old news to me.  Jen had confided in me about her and Amy back when we were in high school, and the story of their initial fun together is tame compared to other stories.  We have nicknames for some of those stories such as “Strip Quarters,” “Night Swimming,” “Pube Shaving Party,” and “Reunion.”  I’ll let Jen reveal those in time.   I’ve never known Jen to be shy in the bedroom, but even after all these years and 25 years of marriage, the last year and half have definitely taken things to an entirely new level of exploring.   I am a lucky guy.

Next:  63. Ice, Ice, Baby Redux – A Solution!