When and How Did Digger Lose His Virginity?

An email list gone awry is the inspiration for this post, as well as my bloggiversary present to all of you.  Someone seemed to misdirect it towards me, but it wasn't a bad question and ties in with one of my earliest posts here.  Apologies to those who read all this stuff on Sensual Dementia, which would have been 2 years old about now.



In "Dead Ringer" I regaled the tale of woe of my first love.  My virginity was still intact at the end of it, even if my heart was not.  While we did many, many intimate things, including getting naked, sexual intercourse was not part of it for Ellen and I.  I wished she would have been my first.  She was not, but she was there in spirit.


I went back to college after having graduated 1 1/2 years earlier.  In some ways, I felt closer to Ellen there, since it was where she went and where we met and where we spent so much of our time.  I was almost a year out when I kissed her under the Campanile, a tradition I never got to participate in as a student.  But this story is not about Ellen.  It's about the loss of my cherry.


While Ellen and I did not go all the way, my sexual side was ignited.  My need for affection, cuddling, holding, kissing and passion…these all fairly oozed out of me.  As a vampire craves blood, I craved the tender flesh-upon-flesh sensations of being physically melded together as one, even if I was not exactly experienced.


Living off-campus as a 25-soon-to-be-26 year-old student, I was more mature that most of my college peers.  I was taking some lower level science and language courses, which allowed me to observe younger-me clones making the mistakes I made my first 4+ years.  But I was a studious adult student.  I hit the books nonstop 8-6 M-F whether I had class or not.  I knew the world of working 18 hour days, so this was gravy.  My evenings and weekends were mine, mostly.  So what to do?


The community newspaper (not the college one) ran personal ads a couple times a week.  On a lark, I went ahead and filled one out, as meeting women in bars was a place I had outgrown, and I had not yet learned about picking them up at church.  In fact, this was a period where I lived a godless, heathen life as much as I wanted. 


Three women answered my little ad.  I met all 3 of them.  One of them, we went out exactly once.  It was nice and lovely, but there was definitely no chemistry.  She was a grad student in the genetics department and had a sister who was a bit of a celebrity in the state of Iowa.


The second was a total flake.  But we did see each other several times as friends.  Again, there were no sparks coming from her.  Her dad was professor at the university and she was just sort of sponging off of her parents.


The third was the one.  Missy did not have a degree, but worked in the university library.  She also had a 2 year-old little boy.  She was upfront about that, and I was more than fine with that.  I was going through a stage where I was really wanting to have babies and kids.  Or at least I thought so at the time.  Our first date nearly didn't happen, as we arranged to meet at a Godfather's Pizza joint.  What neither Missy or I knew was that it was closed.


So, I tried calling her, and reached her sister who was babysitting for her.  The year was 1989, well before cell phones, so we were using these archaic things called pay phones that used to actually be pretty common.    So Missy's sister ended up coordinating us to a Pizza Hut located in the same area as the ill-fated Godfather's.  


Missy had warned me that she had gained some weight and was quite heavy.  However, I did not see this as a big deal.  I wasn't heavy at the time, but I did have this ugly thing going on.  However, Missy sort of sized me up and decided I wasn't too bad.  I suppose that was how I saw her, too.  She was not morbidly obese, just a woman who had a young child and hadn't lost the pregnancy weight.  She also had long red hair.  We had our pizza and shared a pitcher of coke or something and then we went to a bar that had a bunch of pool tables.  I'm not very good at playing pool, but Missy was even worse.  At least we got our money's worth!  We had a couple of beers, and while playing pool, I had a chance to really check her out.  I liked her, and it was obvious that she was nervous and trying to make a good impression for me.  It was an okay date.  We might have ended with a hug, and that was that.  No one would ever guess that there was chemistry brewing.


I did call her a day or so later and we talked quite awhile on the phone.  We actually did arrange a second date, meeting at a hockey game.  More beer was consumed there, and there was a lot more flirty hugging-holding type stuff going on.  No kissing at this point, though.  I agreed to meet her back at her place after the game and after I picked up my VCR and a couple of movies. 


Her son was in bed asleep when we got there, and I met her sister who promptly left.  So we lay upon the couch and snuggled and sort of watched the movie.  Actually we didn't watch it at all.  We were making out and kissing pretty much the entire time.  Things got hot and out of hand.  Really hot.  No, I mean hot as is in sweaty hot.  My body really did get into a sort of overheated state and there was no way I was going to get and stay hard.  So there was some frustrated tension, there.  I went home from the second date, still a virgin.


But there were other dates.  Quite a number of these were booty calls, because I somehow learned the fine art of giving Missy handgasms.  That was SO awesome, and I enjoyed making her come over and over until she couldn't stand it anymore.  But I was still pretty much a virgin.  We were naked and intimate, but it wasn't until I spent an entire night with her that the early morning wood kicked in, and I was able to easily slip inside of Missy.  I was good to go, but didn't come inside of her the first time.  I don't know why, I just didn't.


This story does have a tragic ending.  Or tragic to me, at least.  Every time I came over to Missy's house, I had condoms in my pocket.  Every time.  But I never once used them, and she never made an issue out of it.  In 1989, AIDS was well known, but still it was considered a gay thing.  But there were still all sorts of other things out there.  Not the least of which was pregnancy.


One night I got a real booty call.  Missy and her sister had gone to see some male strippers, and she asked if I'd come over.  The girl was positively smokin' passion when I got there as she fairly threw her sister out the door.  She had a mini skirt on and no panties and she positively ATTACKED me!  Clothes went flying, except for the mini which just got pushed up.  It was so hott.  I mounted up and she was so wet, I easily pushed right in.  Missy was just so totally into me that night.  I came inside of her and she held me right there, hands on my butt, feeling every spasm and pulse and throb.  How I loved having my butt held.  How I miss that.


   I felt a bit guilty about the condoms in my pocket, but this being the first time coming inside of her…I made a mental note to be more careful next time.


However there really wasn't a next time.  I went several hours away for Christmas break and then when I came back, she didn't really want to see me.  She was terse and brief with me on the phone.  I wasn't too good about keeping in touch over break, although I did come down once and talked to her on the phone.  She said she was really sick and didn't want to talk to anyone.


The next time I saw her at a hockey game, she was more reserved.  She did finally invite me to her house to talk afterwards.  There would be no more sexual foolishness, though.  Missy dropped the bomb that she had gotten pregnant from the one time and had gotten an abortion.  I was devastated.


Keep in mind, I was at a place where I thought I wanted babies and kids.  Wanted them really badly!  And I was absolutely opposed to abortion being my fundamental/evangelical (and terribly sinful) hypocritical self.  But I couldn't be too upset with Missy.  Already a single parent, the prospect of having another one was not something she looked forward to.  She simply did not want to bother with the whole pregnancy bit, despite the fact that I had voiced a willingness to take care babies and kids.  I would have gone it alone or at least tried.  But the fact is, I had no idea what I was thinking.  I wasn't thinking, which was the problem. 


In the end, Missy said that she really enjoyed the sex that we had.  The handgasms I gave her were her first ever orgasms, and she really liked them.  But Missy and I had very little in common outside of her bedroom.  In fact, I can't really think of anything.  We had nothing in common politically, spiritually or educationally.  Missy was a nice, handy piece of ass.  Subconsciously, I was avenging my non-loss of virginity with Ellen.  I picked someone as totally unlike her as I could find, and had a fling lasting less than 3 months.


I never told Missy that she was my first.  I was probably only her second after her baby-daddy, and nearly became one myself.  I doubt she really suspected, or maybe didn't care once I started getting her off multiple times.


So much for the loss of my virginity just a few weeks after my 26th birthday.  I was glad to be shed of my cherry, but really had so much more to learn about sex.  Missy and I never had a whole lot of practice, so I never had a chance to get any good at it.  In fact, it would be another year before I would find a partner who would truly educate me in the erotic arts.


The whole abortion thing still bothers me, sometimes, but it was not enough to traumatize me against sex by any stretch.  In fact, I was determined to make up for lost time.  In 1990, there would be 4 new partners making it my most promiscuous year ever.


Happy Bloggiversary




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