My First Time

Guide For Deflowering A Man

Listen Later
Guide For Deflowering A Man
Former fundamentalist begins her ministry to virgin men.

By April601.

Listen to the ►
Podcast at Steamy
Stories.



" type="audio/mpeg">

In my early 20’s I dated a guy named Terry. He was a

nice enough guy, very respectful and polite. He was my age and not the typical
bad guy type that for some reason I seemed to attract or was it I was attracted
to?

I began dating him and soon realized he was on the more

serious side. Honestly, I didn’t expect that he could hold my attention
for more than a couple of dates.

After somewhat of a wild start to my sexual journey I

reached a point of self-respect and I had established a few ground rules for
myself that I tried to follow. The first rule being that I tried not having sex
on the first date! Well, I tried anyway; bless my heart. If I managed to get by
that crucial rule, I had made up a few more hypothetical rules.

  1. First dates were limited to heavy kissing only.
  2. Second dates limited to touching, exploring. I would allow
    3. my date to touch my breasts and I would go no further than rubbing his
    groin thru his pants.
  3. Third dates maybe a hand job.
  4. Fourth dates possibly a blowjob, and
  5. If we made it the fifth date there were no limits.

    6. I thought these were reasonable limits for semi-nice girls,

    which I considered myself as being. If you haven’t heard how I was still
    a naive, shelter, fundamentalist virgin when
    an older married man deflowered me, we’ll need to have that
    conversation; because it explains a lot of my personal journey and progression
    toward sexual awareness of myself. It also added to my empathy for others with
    retarded sexual awareness in adulthood.

    I remember telling several of my dates these rules but

    honestly, I don’t ever recall a time when I was able to really stick to
    them; except with Terry.

    My first date with Terry ended with us just kissing and

    making out in his car. It was all pretty tame and controlled overall. He was
    polite and seemed to respect the limits and restrictions I was trying to
    follow.

    Some guys are just terrified of sexual intimacy; and need encouragement

    and affirmation. Some guys are raised to think that all women view sex as dirty
    male desires, that women inwardly abhor, and only tolerate in marriage
    arrangements.

    After our second date we again began to make out in his car.

    As things started to heat up with Terry, I reached into his pants to do an
    assessment of his manhood. I liked what I felt as it appeared to be a good size
    and worthy of a third date. Never being the patient type, I unzipped his pants
    and pulled out his cock. Yes, I know; I broke my second date rule.

    As I began to play with my new toy, Terry stopped me and

    said he had something important to tell me. Really? I’m stroking your
    cock, and you want to stop and talk? This was a first for me.

    He sheepishly told me he was a virgin! What! Really! He now

    had my attention. I wasn’t sure if I believed him. I thought maybe he was
    playing games to entice me into having sex with him. He was a good-looking guy
    but a bit on the shy side, so maybe I could see it. I guess I must have overreacted
    as he immediately went limp. I apologized and that was pretty much the end of
    the date.

    I wasn’t sure what to make of it. Is this good or bad?

    Should I go on a third date or run?

    The next day I called my friend Jenny. She always had

    answers. I told her everything and wanted her take on the situation. Not to be
    mean but we did have a good laugh over it. Jenny had never been with a virgin
    before either. We both pondered over it and the more we discussed it the more
    intrigued we both became. We jokingly came up with the term “Virgin
    Boy.” But his sudden limpness was a result of my failure. He needed me to
    help him overcome his insecurity, and I’d just magnified it, instead. I
    owed him a do-over, if he’d even let me have another chance.

    Jenny pointed out that guys think about sex hundreds of

    times a day. So if I were his first, he would probably then think of me every
    day for the rest of his life. Wow what an emotionally powerful thought that
    was.

    “Imagine being his very first, the first girl he has

    sex with. You will always be remembered as ‘The One’,“ she
    said. “The one he lost his virginity to. You will always be special to
    him. You will forever be engraved in his memory. Even when he gets married;
    when he is 40 and is mindlessly daydreaming on his drive to work; when he gets
    old and reminisces; it will always be you that he thinks of when he thinks of
    his very first time.”

    The more we talked about it the more we realized what a

    great opportunity this was. I think the thought of taking his virginity was
    turning us both on. By the end of the evening with Jenny, it was decided I
    would be his first.

    But we also agreed that it had to be special, not just a

    quick hump in the car. This was becoming a huge responsibility for me. I had to
    do it right. It had to be extra special. I felt an obligation to make it
    special.

    Jenny was dying to meet Terry so when he called for a third

    date, I told him my friend Jenny would be joining us. We all met at a bar and
    Jenny loved him. She gave me her approval but also had a suggestion. “How
    about for his first time he has a threesome with both of us? How special and
    memorable would that be!” I had threesomes with Jenny before during
    vacations, so it wasn’t out of the question. I told her I would have to
    think about it. I did have concerns, though.

    A threesome sounded like a great idea but I knew that Terry

    would end up remembering Jenny and not me. Jenny was a bombshell. She was
    gorgeous and outgoing. Bigger curves, cute as fuck, guys were drawn to her like
    a magnet, that’s one of the reasons I loved hanging around with Jenny.
    She could be overbearing also. Sure, Terry would love to have sex with Jenny
    but what about me? What about me being “the one”?

    As the weeks went on, I was doing my best to refrain from

    sex with Terry. He was cute and nice but really, he wasn’t anything
    special, he was just too serious for me. But Terry was a virgin, and this made
    him special to me. Taking his virginity was all I could think of. If he
    wasn’t a virgin, I’m sure there wouldn’t have been a third
    date. He was in my head or was it his virginity that was in my head. I was
    determined to take his virginity.

    Up until this point I had dated older guys, and I was having

    sex on a fairly regular basis. With Terry I was not doing well without sex.
    Terry thought I was the good girl type by not having sex. Yes, I was sweet and
    innocent looking. But the lack of sex and the erotic thoughts about taking a
    young man’s virginity were driving me crazy. Self-gratification
    definitely increased during this waiting period.

    I finally told Jenny that I wanted Terry for myself. I

    wanted him to remember me, not ‘Jenny and that other girl’. Besides
    it was me going without sex all these weeks. I needed his full attention. Jenny
    seemed a bit disappointed, but she understood.

    Jenny and I came up with a plan. As both Terry and I still

    lived at home I suggested a weekend away in Niagara Falls. The honeymoon
    capital of North America, how appropriate was that?

    Terry agreed and I was so excited. How could I make this

    special event even better?

    Leading up to the weekend, I daydreamed how it all would

    play out. Would he ejaculate before we even start? Should I tease him or maybe
    just jump him? What should I wear? It was all I could think of. I was horny as
    hell in anticipation.

    I bought a new nightie for the occasion. There really

    wasn’t much to it. It was short, sheer, and low cut, not much left to the
    imagination.

    The day finally came. The long drive to Niagara Falls was

    filled with sexual tension. We chatted and joked during the drive, but my mind
    was racing. I couldn’t believe how aroused I was. I don’t think I
    ever thought about an impending sexual act as much as I did with Terry. I tried
    to rationalize it, after all we all lose our virginity at one point, but
    psychologically this had become a big deal for me. Maybe because my virginity
    was taken from me by a man ten years older than me that was only concerned
    about his own sexual gratification.

    Now the shoe was on the other foot. It was my responsibility

    to make sure Terry’s loss of his virginity was a memorable and wonderful
    experience. Dam I was so thoughtful.

    We arrived at our destination and checked into a cheap

    motel. I will always remember the name “The Rainbow Motel.” Terry
    was eager to begin and began groping me as soon as we entered the room but I
    quickly put a stop to it. I had a plan; this was going to be a slow seduction.
    We unpacked, freshened up, and went to get a bite to eat. No alcohol for either
    of us, I wanted him to remember this special night.

    Once we got back to the room, we sat on the edge of the bed

    and started kissing. As things began to heat up I told him to get naked and in
    bed. I went into the bathroom to slip into my nightie. I slowly walked out of
    the bathroom and around the bed to make sure he got a good look.

    I dimmed the lights but kept it the room bright enough so

    that he could see everything that was about to happen to him.

    I could see his arousal as the bed sheet was poking up like

    a tent. I slowly and sensually touched him as I stood over him. I told him he
    wasn’t allowed to touch me. The lingerie I was wearing was totally sheer,
    so I wasn’t hiding anything.

    I slowly pulled back the sheets and crawled into bed with

    him. His cock was standing to full attention as he lay there. I could see he
    trimmed his hairs for the occasion. How sweet.

    I reached down and grasped his cock in my hand. I squeezed

    it tight as I stared at it. I could feel the pulsating blood as it gushed
    through his veins. I felt a sense of power as his virgin cock throbbed in my
    tight grasp. After many weeks of planning and anticipation the time had finally
    come. His virginity was in my hand. No pun intended.

    I slowly began stroking him. I was very conscious of the

    possibility of him pre-ejaculating to my touch. I proceeded with caution. I
    didn’t want to over stimulate him. As I stoked him, I could hear his
    breathing picking up. I slowed down and began to coach him. I wanted this to
    last. I was in total control, and I loved the feeling it gave me.

    I had thought it best to proceed and give him his first

    blowjob before he exploded in my hand. I slowly and seductively began kissing
    and licking his beautiful cock. Exploring his balls with my tiny fingers. I
    slowly lowered my mouth onto the tip of his cock and began slowly bobbing up
    and down, taking more of him inside of my mouth with every stroke. He was doing
    great and by now I was getting right into it. I began stroking and sucking his
    cock vigorously. I then moved down and began sucking and licking his balls.
    Placing first one them both in my mouth as I stroked him hard and fast.

    I was hot and horny as hell by now and he was getting the

    full treatment. I wanted him to cum in my mouth and I wanted to swallow his
    first blowjob load. This was all part of my plan.

    Despite my best efforts he wasn’t ejaculating! This

    was not what I was expecting but I carried on.

    It was finally time for me to take his virginity. I was so

    wet with anticipation. I pulled my nightie off, so I was completely naked for
    him, my plump tits swayed and jiggled to his visual delight, as I straddled
    him. I was going to make this special for him. I already had decided I
    wasn’t going to use any protection to diminish the feeling, bareback
    only. I wanted him to feel just how good sex can be. I proceeded to mount his
    stiff rod. Ever so slowly, I wanted him to feel every inch of me as I slowly
    lowered myself onto his hard throbbing cock. I was soaking wet as I easily
    engulfed his entire cock deep inside of me. He grabbed and squeezed my swaying
    breasts. My nipples were swollen and erect. I was primed and ready.

    Slowly I began riding him. I was taking it slow and easy, as

    I didn’t want him to cum too fast. It felt so good to have his cock
    inside of me. The thought of finally taking his virginity was too much. He had
    barely entered me and immediately began having an orgasm. I shook and quivered
    as I began riding him faster. Oh my god! it was me that was pre-ejaculating and
    not him. Terry thrust deeply and pulled on my nipples as I let out a deep moan.

    I was still deeply implanted on top of Terry as I regained

    my composer. He was still rock hard, so I continued to ride him. Soon I was
    riding him like crazy. I was bouncing on him like wild as he had a tight hold
    of my hips thrusting me down on his cock. He was giving it to me right back to
    me. I was riding him so hard and violently I was pretty sure something was
    going to break. Was it going to be the bed or his cock?

    He wasn’t ejaculating. I was so aroused about taking

    his virginity I came once again. This time was even more powerful than the
    first. My whole body shook as I had violent spasms. I let out a loud deep moan
    as I had an orgasmic eruption. In my twenties it was very rare that I climaxed
    so having two orgasms on the first go was incredibly rare for me. My juices
    were flowing. I needed a good fuck after going without for so long and he was
    giving it to me.

    Then it hit me…what’s going on here? If he

    really is a virgin why hasn’t he ejaculated yet? I was convinced he had
    done this before. This couldn’t possibly be his first time. Was I being
    doped? He just kept fucking me hard and fast. Eventually I had to stop. I was
    confused and yes maybe even a bit angry for being lied to. “You said you
    were a virgin. why aren’t you cumming?”

    He apologized and explained he was used to very frequent

    masturbating, and this felt; well, different. It felt great, but just
    different. I suppose that is possible? He seemed to have no idea that frequent
    jacking off could diminish his responsiveness with a woman. I could tell by the
    look on his face he was telling the truth. I also realized that a
    frequently-masterbating man performs better when he can stroke a pussie fast,
    furious, & freely; so I should not be riding cowgirl, tonight.

    After a bit of hugging and kissing, I went back to work and

    started with a nice long blowjob. I was determined not to stop until I
    swallowed his load. I encouraged him to stroke his cock while I sucked his
    bulbous tip and manipulated his balls. With his assistance we finally had him
    cumming in my mouth and he gave me a huge load to swallow. Hurrah, success at
    last. I was proud of myself. His confidence was restored and still rising.

    I sucked and swallowed every last drop and even licked him

    clean. This was his first time, and I was being extra nice to him. I was making
    it special. I wanted to set the standard high for all future blowjobs. A
    standard that every other woman he slept with had to be compared to. Yeah, I
    gave him a great first blowjob!

    Once he recovered, he mounted me missionary style and we

    both watched as he slowly entered me. We both began moving in rhythm as he
    fucked me.

    I began encouraging him to fuck me harder, I could tell he

    was getting worked up and it wouldn’t be much longer now. He loved the
    nasty language I used as I assured him of his prowess. He loved hearing how
    much my pussie loved his cock inside me. His self-confidence was naturally very
    fragile, being a virgin in his twenties. I needed to unleash the beast in him,
    and I knew he needed my affirmations to get there.

    As he was getting close, I told him to cum inside of me,

    that I wanted to feel his warm cum deep inside of me. He came hard and fast. I
    screamed out “yes! Oh, my, god; yes” as he filled me up with his
    warm virgin cum.

    He made me work for it, but his virginity was finally mine.

    I will always be remembered as, “The One,” that will be remembered.
    I think I was thrilled more than him.

    That weekend we had sex 20 more times. Yes, I kept count, 20

    more times. We were like newlyweds. Terry just couldn’t get enough, and I
    never refused him. We tried several positions, failed at a few, and even
    laughed together at our lack of gymnastic acumen. There was no way he would
    ever forget me after that weekend.

    When I got home on Sunday night, I swear I was walking

    bowlegged. I was exhausted and sore. I couldn’t wait to tell Jenny. I
    felt such a sense of accomplishment.

    I was hooked on the sense of power, control, and the

    adrenalin rush I had felt.

    • The planning, anticipation, and buildup of finally taking
      • his virginity.
    • The epic orgasm I had felt when I finally had his cock
      • inside of me.
    • The psychological pleasure I felt, knowing I was forever
      • special to someone.
    • That this memory would never be forgotten by either one of
      • us.

      I wanted to do it again; I couldn’t stop thinking about

      it. I wanted to experience another virgin boy.

      Since then, I have experienced several virgin boys. I will

      share my adventures about deflowering them, in time.

      PS, I continued to date Terry for a couple of months

      afterwards. During that time he became quite proficient at sex. I was thrilled
      to be the experienced woman that taught him all about sex. It was quite a rush.

      By April601 for

      Literotica

      ...more
      View all episodesView all episodes
      Download on the App Store
      My First TimeBy (various)