(Women will like this TRUE story more than guys) I met my older brother and several of his friends at a bar to say goodbye one evening shortly before I was shipping off to boot camp. I was leaving in four days and wouldn't be seeing him again. I was only 18 but had a fake ID as most of us did in those days when the drinking ages were all on the rise. My friend David was with me; he and I planned to just bum around together for the next few days.
I ended up sitting between my brother and his friend Brenda. She was a pleasant, good-looking, voluptuous brunette whom I had met numerous times before. We had a few beers and just chatted and laughed about things. David and I both thoroughly enjoyed being accepted by an older crowd and being included by my brother.
After a few hours of this, it was time to go while we could still function. I had earlier mentioned that I was staying in a hotel for my last few days in town. As I stood up and was telling Brenda that I had enjoyed her company, she looked me coolly in the eye and said, "Would you like to take me to your hotel room?"
I must have looked like an idiot for a moment, staring blankly back at her as I digested what she was asking me. I was trying to figure out if I had heard her correctly, if she was asking what I thought she was asking. I had always enjoyed looking at Brenda's body, her generous breasts and her curvy ass, but had never thought about her in a sexual way because it had never occurred to me that a mature woman like her would be interested in me. She was a professional career woman who had just turned thirty and owned her own home. She had been married and divorced and lived a real life and here I was, a mere pup of eighteen years. I had never had much luck with girls my own age and here I was being invited to have sex with a real woman. It seemed to take forever for me to go through the mental gymnastics, but I doubt more than two seconds elapsed. I had no doubt that I wanted to be with her, but I did doubt that she was really asking me to.
"Sure, " I finally responded. She grinned at me and I knew then that I understood correctly. The look in her eyes told me that I was really in for something. She took my arm in hers--giving me an erection that would cut wood--and brought me to stand by my brother. "I'm taking your little brother off to have my way with him" she said with a laugh.
That was the first time I ever remember seeing my brother speechless. After he finally picked his jaw off the floor he simply said, "Have fun. Make sure he gets to the Navy on time."
I had almost forgotten my friend David in my excitement. Brenda and I went over to him and I said, "Uh....hey...something's come up." He looked back and forth between us, at two people grinning in anticipation and oozing sex. He was obviously going through some of the same thoughts that I had just moments earlier.
"Uh, Dave....I'm really sorry, but I'm going to go with Brenda here. I hope you don't mind. Why don't you just stay here with these guys?" I felt a little bad about it, but this was certainly well within the "guy code". Besides, I couldn't count the number of times that David had blown me off to go be with his steady girlfriend. At any rate, there was no way in hell I was going to miss out on this opportunity. He took it good-naturedly and we were out of there.
As we walked outside, Brenda put her hand brazenly on my ass, squeezing my cheek and telling me she couldn't wait to get me naked. You can imagine the effect all this was having on a young, fairly innocent, fairly inexperienced guy. I was having a hard time maintaining my composure and thinking clearly in my excitement.
Fortunately, my hotel room was close and we made it inside quickly and without being accosted by the police for indecency. We threw our arms around each other and kissed hotly for some time, standing just beside the bed. I was lost. I had never been kissed so passionately or so thoroughly by the few young girls I'd been with. I got into it and returned as best I could, reveling in the sensations going through my body.
She was frantic to get my clothes off, pulling my shirt over my head and tearing at my jeans. Between the two of us, we managed to get each other naked very quickly. I had been looking forward to this and greedily put my hands on her luscious breasts. They were very generous and nicely shaped, with small pink circles and long, firm nipples. I had never touched such mature, wonderful breasts in my short life. I leaned toward her and took her nipples alternately in my mouth. She responded by moving her groin against mine and grinding into my rigid cock. I moved my hands to her curvy ass and pulled her hard against me, stroking my cock against her.
This was enough foreplay for both of us. She moved backwards to the bed, pulling me onto her as she lay on it and both of us moved towards its center. We kissed and groped each other for a moment until she said, "I want you inside me now."
"Brenda, I'm afraid I'm going to cum too fast. I'm so turned on I could easily cum right now, and I'm not even inside you."
She responded with a smile, "Don't worry sweetie, I want you to cum in me no matter how quickly. I know you'll be ready again soon and I plan on using your body all night."
I was sold. She was wet. I was inside her seconds later. She felt fabulous. Her body embraced and welcomed me, in sharp counterpoint to the feelings I'd had with the few previous girls I had penetrated--almost as if they had been fighting my cock on its way in. Brenda was so wet and ready for me, eagerly pulling me toward her. I held her in my arms close to me and still for a moment, enjoying the feeling and wanting to record it for later, hoping that I wouldn't spill my seed in the next few seconds.
I calmed myself and kissed her for a few minutes, staying deep inside her and touching her. I was mesmerized by the sensations of being inside this lovely woman.
To my surprise, I didn't immediately shoot off and embarrass myself. This sensation was so different from my previous frantic experiences that I was able to enjoy it for an amount of time that surprised me. Brenda kept up a stream of talk, constantly encouraging and directing me. She pulled her legs up close to her chest, aiming the head of my cock at her g-spot (I was oblivious of its existence and purpose at the time, but she was clearly not). She had apparently been just as aroused as I was--within moments she was moaning sharply and moving toward a quick, sharp orgasm. As I stroked in and out of her and she cried out, I joined her, releasing myself into her. This pushed her further and we rocked back and forth against each other eagerly.
She released her legs and wrapped her arms back around me and we began kissing again. After a moment, she began grinding against me, and then suddenly opened her eyes wide in surprise. "My God! You are still hard!"
"I am? Are you sure I'm not just hard again already?" I asked, being ignorant of my own bodily response.
"You didn't lose it at all. Get busy and start moving again, I want you to cum again."
I was so aroused and enthralled by this mature and sexy woman that I'd have done anything she suggested, anything at all. I found it hard to believe that I had maintained an erection through that orgasm, but I wasn't going to question it. I worked hard against her body again, and again she pulled her legs back so I'd hit her g-spot. She came again soon after, her face grimacing and her hair shaking as she cried out unintelligible words, mostly "Uhhhhhhh!"
"Let me be on top of you, " she said, rolling us both over. I laid back and watched her ride me, loving the feeling and the view I had never experienced before. It was easy for me to hold off this time, enthralled by the experience more than the physical sensation. Sweat broke out on her entire body as well as mine. I watched her cum yet again, her hair flying and her round breasts shaking. I kept my hands on her ass throughout, squeezing her cheeks and enjoying her movements.
She fell on top of me to rest for a moment and to give me more passionate, appreciative kisses. I loved touching her soft skin and caressing her back and ass.
I had built up some confidence by this time since she hadn't thrown me out of bed or stormed off in disgust, so I rolled her off of me and told her to get to her knees. I moved behind her and entered her as I took her breasts in my hands. I began to ride her vigorously, my hips slamming into her sexy ass as my cock slid in and out of her. I loved watching her back and her ass moving; this turned me on to no end--ever since, this has been my favorite view of any woman's body. I came again, violently. She screamed as I did, which I took as a good sign, and then we lay down on the bed holding each other.
I can't recall exactly how many times we coupled again that night; it was twenty-two long years ago, the entire span of my very full Navy career. I do know that we got out of bed and stood up to have sex at least once and that she rode me several times and I rode her from behind several times. I am sure that I came more that night than almost every other night of my life. I'd like to think that she did as well.
I woke up in bed with a naked woman for the first time ever and kissed her awake. She rolled me on my back and said good morning to my cock with her lips, then climbed on top and rode me for another orgasm for both of us. This time I could see her in the morning light and thoroughly enjoy the sight of her breasts moving above me and the expression on her face when she came.
While she made coffee we discovered that we were both starving, so she suggested that we shower and get something to eat. At this point, I was surprised that she was still around and hadn't gone off to do whatever it was that adult women do during the day. Little did I know that I was in for another shocker. "Why don't you check out of your room and come spend the next few days at my house?" she asked with an impish grin.
"I can't imagine anything I'd rather do than spend these last few days with you."
We showered together and I soaped her sexy body all over, concentrating on her fabulous breasts and then her generous, shapely ass. I took her from behind while I soaped her front, making her cry out loud again as she came. These days were full of brand new experiences for me, including this one--showering with a sexy woman and entering her without stopping to ask if it would be okay.
Once we got to her house, we headed straight for the waterbed that I had sold her a few weeks earlier when I gave up my apartment. She asked me to taste her and taught me how to do it well and how to make her cum reliably. When she showed me how hard she could cum from that and how much she enjoyed it, I became a convert to the cult of cunnilingus. I was amazed at the power this gave me over her body and how affectionate she felt towards me afterwards. To this day, I love going down on a woman who enjoys it more than almost anything.
We spent the next three days together, most of it in bed. She did let me sleep in the next day while she went in to work briefly and arranged things for days off, but for the most part the real world did not intrude. We watched some movies and had some food delivered, but mostly just lay around naked together either in the afterglow of sex or working each other up towards more.
I became addicted to going down on her and making her cum hard, and then entering her to do it again. I got spoiled being with such an orgasmic woman so early in my sex life. She sent me a very nice letter in boot camp, but by the time I ever visited my hometown again she had settled down seriously with another man and I stayed away. I remember thinking what a lucky guy he was to be with such a sexy woman.
Brenda was my first in so many ways: --My first older woman --the first woman I 'shacked up' with --the first woman I slept all night with --the first woman to ever wake me up with her mouth on my cock --the first woman to ever 'pick me up' --the first woman I ever gave an orgasm to through oral sex --the first woman I ever made scream during sex --the first woman I ever saw get sweaty from sex --the first time I had sex in a hotel --the first time I had a woman on top during sex --the first time I had sex in the shower --the first time I had sex standing up
I will never forget her. I will always be grateful. Boot camp was so much more tolerable after those days with her, but I was never happy with young girls again--even now I prefer a more mature woman to a younger one. Fortunately, I did experience a few other older women after that who also taught me a few tricks.
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<a href="https://www.lushstories.com/stories/mature/my-first-older-woman-on-the-way-to.aspx">My first older woman - on the way to boot camp</a>