The setup to this story is all true. However, the sexual events only occurred in my mind as what I wish would have happened, and are merely for my enjoyment as a writer and others’ enjoyment as readers. I’ve changed the names of course.
My name is Keith, I was 18 and in my freshman year of college at a small Midwestern University. I was a music major, trumpet my instrument of focus. In addition to many other musical endeavors I was in the jazz band. That winter the jazz band was taking its’ biannual trip to Hawaii to escape the snow for a week and play some gigs in Honolulu. Family was allowed to come along on the trip. At the hotel in Hawaii it was 4 to a room. My roommate Jon, a fellow trumpeter, and I shared a bed. Also in the room was Jon’s long time girlfriend Sara (who played sax in the band) sharing a bed with her mom Jackie. I was a little surprised they let us all room together but I guess I was an adult now, not in high school anymore.
Jon’s girlfriend Sara is very athletic, nice body, not the prettiest face. Though as the only way I’d ever known her was as Jon’s girl I’d never really thought about being attracted to her. Jackie, on the other hand, I found I was very attracted to. Yea she was an older woman, but damn did she still have it. She was single at the time. As an aside, Jackie is now remarried to a very rich older man. I don’t know what the guy does but his son writes all the music for a very famous American pop singer, no bullshit. This guy’s loaded; a testament to Jackie’s hotness. Not saying the guy doesn’t love her and she him….but you know how it goes.
So after our first full day in Hawaii, as we got in at around 6am, I was pretty tired. I was also pretty worked up seeing all the barely covered flesh on the Waikiki beach. I decided that before I went to bed I’d go into the bathroom and rub one out. Jon, Sara, and Jackie were down in the bar so I thought I had the place to myself. I turned on that overhead fan thing hotel bathrooms always have to drown out any little noises I might make just in case someone came back while I was busy. I guess I must have forgotten to lock the door ’cause just as I was getting ready finish Jackie walked in and saw me sitting on the edge of the tub, my rock hard cock in my hand just about to burst. She was wearing a bikini with a towel over her shoulder and even though my hand stopped moving as soon as the door opened that sexy sight was all my dick needed and as she looked at me in surprise I came all over the tile floor.
I looked at Jackie in horror and tried to cover myself. I could tell she was a little intoxicated, and she just smiled and said “make sure you clean that up big guy.” With that she closed the door and left me to myself. I cleaned up the cum and took a hot shower, not wanting to think about how awkward it was going to be around her for the rest of the week. As I got dressed and walked out into the room she was sitting on her bed reading a book. Jon and Sara were still out. She was now wearing a thin fabric floral print robe that was revealing quite a bit of leg and cleavage. She looked at me over her glasses in an extremely sexy manner. She could tell I was tremendously embarrassed. “Don’t worry about it Keith. I have a son too, I know how you young guys are. I won’t tell anyone.” I didn’t know what to say so I just said “thanks” and went down to the bar to join Jon and Sara.
The next morning I was up quite a bit earlier than Jon and Sara, they had drunk fairly heavily (they were 21) the night before. I went out to have some fun in Honolulu but by the time 3pm rolled around I starting to feel really jet lagged. I called Jon and Sara to see what they had gotten up to. “We’re at the zoo” said Jon. “We’re probably gonna head to the aquarium after this and then to the beach for a while before dinner. We’re going to eat at Dukes at 7 if you want to join us” “Sure, I’ll see you guys there.” “Sounds good buddy, seeya.” I hung up the phone and decided to head back to the hotel to catch a little bit of a nap before dinner since I would have the room to myself.
As I entered the room I saw Jackie sitting in her bed under the covers, again reading a book. “What’re you up to?” she asked. “I was just going to take a bit of a nap, feeling a little jet lagged. I don’t want to bother you though.” I was still embarrassed about the previous night. “No, don’t worry. You go ahead, I’ll be quiet” she replied. “Thanks” I said. I went into the bathroom and changed into my boxers and a tank top and quickly got into my bed. “Haha, you don’t have to be embarrassed. I saw a lot more last night” Jackie chuckled. I’m sure my face went completely red. “Yea, sorry about that” I apologized again. “You don’t have to apologize, it’s ok. Hey I kinda liked it. It’s been a while since I’ve seen a handsome young man having an orgasm.” I turned to look at her with a cocked eyebrow. ‘Did she just come on to me?’ I wondered to myself. “Tell ya what” she said with a smile. “Why don’t you come over here and join me in this bed.” She pulled back the covers to reveal a beautiful, and totally naked body. I just stared for a moment. I couldn’t believe how pert her breasts were. Her stomach was flat, her skin taught, and her pussy clean shaven. She would have been hot for a 20 year old, let alone a 40 year old. “C’mon” she said, snapping me out of my trance. “We’ll have some fun.”
“Are you sure? I mean, Sara is my friend, and…..well, really?” I stammered out. “I’m sure, it’s fine. Come on over here, and just go ahead and leave those clothes in that bed.” I slowly pulled off my tank top, still considering this proposition. “That’s it, now the rest” she said, watching me keenly. My dick was already raging hard and pressing against my boxers. I stripped them off and stood up. As I walked over to her bed my hard cock bounced up and down. I could feel it’s weight and the pressure of it straining against its own size. Though I am fairly well endowed at 7 inches long and pretty wide my dick just kept wanting to grow.
I lay down next to her as she threw the covers over me. The bed was warm from her body. She set her book down and took off her glasses. “How old are you?” she asked. “18” I said, I think my voice rose about an octave as I said it. “Have you been with a woman before?” she asked. “No, I’m….I’m a virgin.” She smiled at this. “Well, I’m sorry then.” I looked at her quizzically, my lust growing like a mushroom cloud inside of me. “Why are you sorry?” “Because when you lose your virginity to me you’ll never be satisfied by a woman again.” I looked at her with a look of astonishment on my face. I pulled myself together a bit and said “Well, I guess that’s burden I’m just going to have to live with.” With that she pulled me in for a passionate kiss.
Our warm bodies pressed together as our tongues began exploring each other’s mouths. We wrapped our arms and legs around each other and my granite erection gently rubbed against her leg as we kissed. She grabbed one of my hands and placed it on her breast. It was amazing, I couldn’t believe how well rounded yet supple it was. I began squeezing her breasts one by one, tweaking her nipples occasionally. She began slowly running her fingernails along my side and stomach. With each sweep she moved lower and lower until finally she started circling the base of my penis with her fingers. She pulled away from me for just a moment. She could see in my eyes that I was dying to have her grab my dick. The absence of touch upon it when I was so aroused was like torture. “No touching yourself, you need to touch me first.”
She took my wrist and led my hand down to her bald pussy. She leaned in close again and began whispering into my ear what she wanted me to do. As she directed my fingers she also told me “Suck my nipple. Nibble my ear. Lick my neck, pinch my nipple.” These were the instructions I received in a quiet, airy voice filled with pleasure. Soon she began to take in sharp breaths. “Keep going” she gasped out as she began to reach climax. I kept my fingers moving, sucked on her neck, and pinched her nipple. This was enough, and she began bucking her hips uncontrollably. The breathy noises she had been making turned into moans and screams of pleasure. I kept working on her body until she began to calm down. “Mmmm, pretty damn good for your first time.” “Well, I’m a virgin. But I have fingered a couple girls before.”
She smiled at me and said “In good time baby.” She pushed my shoulder until I was lying on my back, my dick still making a tent out of the bed covers. She got up on her knees and positioned her pussy over my face. “Give ‘er a bit of a lick for me.” I buried my face into her sweet pussy and began lapping up all of the sweet moisture she was producing, which was a lot. It only took about a minute and she quickly shuttered into another orgasm. “Ok” she said as she recovered. She looked down at me from her kneeling position, her crotch still in my face. “Your turn” she said.
She gently grabbed my penis which alone was enough to cause me to gasp in a huge breath. She laughed a bit at my ecstasy. She started by slowly pumping my dick up and down. She got off her knees and began kissing my chest. She circled my nipples with her tongue before taking them into her mouth one by one. She sucked them hard and even bit them, slowly increasing the pressure until she got a reaction out of me over and over. She kissed and licked her way down to my dick. She kissed the head gently and then straddled me.
She positioned herself right over my erection which she grabbed and placed the head of at her entrance. “Ready?” she questioned. “Very” I said with unsuppressed anticipation. She slowly began to lower herself onto me until she was all the way down. “Damn your big, it’s been a while, but you feel huge nonetheless. My god that feels amazing.” “Glad you like it” I said. Not a great line, but my mind was too preoccupied to be trying to come up with good lines. She slowly started to bounce up and down on my dick. It was amazing, she felt so good. “Now start to go back and forth in rhythm with me. You’re a music major, you should have rhythm.” She smiled at me.
I began bucking my hips to match her speed. It didn’t take long before I could start to feel the orgasm building in my balls. “I’m not gonna last long” I said. “It’s ok, I had myself fixed after two kids. Just cum in me, but I’m gonna ride you hard until you do.” With that she went to town on my dick. She placed her hands on my stomach and bounced up and down at a ferocious speed. My body was sent into pleasure overdrive as my orgasm burst itself through my dick and into Jackie. I could feel my cum dripping down the bottom of my dick and over my balls. Just as I was finishing Jacking screamed with one final orgasm.
She dropped off of me and curled up next to me. We both fell asleep then. Well, at least I did, I’m not sure if she did ’cause the next thing I knew she was down at my penis with it in her hand. “Time to get up” she said. She put my flaccid dick into her mouth and began sucking. It felt amazing. As my erection quickly rose she started pumping me with one hand, sucking on my head, and massaging my balls with her other. It didn’t take long for me to get hard and then it didn’t take long for me to blow my load right into Jackie’s mouth. She swallowed it down with a smile; an act so sexy I swear I almost came again just watching her. “Come take a shower with me, we need to get cleaned up before we go meet Sara and Jon for dinner.” I obliged her and we had a nice shower where I fingered her to another orgasm.
Jon, Sara, and I are still friends to this day. That was the only time Jackie and I messed around with each other, and like I said, she’s now remarried. That’s too bad, ’cause just like she said, I’ve never had it that good again.