I present to you a story based on actual events, only the names of the people have been changed to protect those people from possible embarrassment…
Chapter 1: The Plan for Vacation
Without a woman in my life I embarked on a vacation with three of my best friends. We had often vacationed together, but this was the first time in a long time. This year the group consisted of my friend Lisa joined us having just had just left her husband of 8 years and my two other two friends were Abby and Jack. Abby I knew since college and her husband Jack I had met senior year at a mixer Abby brought him to.
I always had feelings for Abby, never getting the nerve to do act on those feelings because senior year Jack proposed and she accepted. It was a fact that over the years Abby had given me signals repeatedly both in college and after but I was never able to get the strength to pull the trigger. I figured the best thing I could do was to be happy for Abby and her relationship with Jack, but I could not let go of the feeling that I let something slip through my fingers.
The four of us arrived at the vacation house, I picked up my bags, headed inside, and right in front of me was Abby. I admired her perfectly round ass bouncing in front of me, perfectly formed in blue jeans, and thought about the missed opportunity. I needed to see how it felt to touch her just once before she said, "I do" at the wedding. I reached out to touch her ass and inches from my goal Jack came up from behind me, forcing me to quickly drop my hand and pretend as if I was doing nothing.
I let the thoughts of Abby fade and turned my thoughts instead to Lisa. You see Lisa was older than the rest of us by about 10 years. She was in her mid thirties when we were in our twenties so in comparison to the rest of us she was the old one. I met Lisa when I was in high school when she worked for the school as a tutor. We slept together my last year of high school, my first time with any woman and we kept an open relationship for years. Abby was marring another man in a few weeks, but I had insurance that I would not have to spend the whole week thinking about her, I could at least fuck Lisa.
Chapter 2: My Longing for Abby Grows.
After two days on vacation I could not shake the thoughts of Abby, wondering about opportunities lost. On the third day of vacation, I was sick of these thoughts always in my head, and made an effort to put them elsewhere. I walked the house focusing on the walls doing anything to redirect my thoughts. I went up stairs to go to my room, when a pair of soft hands covered my eyes from behind. Then I heard it, the voice that melted my heart and made my knees weak. Abby whispered in my ear, “Guess who?” I laughed pushing her hands away and turning to see her perfect frame standing before me. The light from a nearby window hitting her face perfectly, she was stunning.
She stood 5 feet 5 inches about 15 pounds overweight, she carried her weight in her tits, her ass, and just a little on her stomach. She had long brown hair that stopped a few inches below her shoulders. She smiled, “So, Jack and I are going for a walk we will be gone for about an hour.” Do you want to come at all?” She asked the question in the way that somebody asks something to be polite but really only wants to hear one answer. I just nodded no and she turned without a word, her perfect ass bouncing as she went.
Chapter 3: Me and Lisa
I turned again to go to my room as I entered I heard another voice calling out. It was Lisa then time calling me into her room. I walked in planning to sit on the bed but as I walked in, I found myself falling into Liza's arms. I felt the warmth of her trim athletic body pressing against mine. Her dark brown curls that rested on her shoulders now tangled with my own sandy brown hair. She stood 5’8 and I was 5’10 so when I placed by head on her shoulder I got a decent look at the top of her well-rounded B-cup’s hiding in a tightly fighting blouse.
“What’s wrong sweetie?” I walked over to the bed with my head sinking to my chest. Taking a deep breath I said, “I need to tell you something.” “I think I have some feelings for Abby.” She laughed semi-nervously, “I’m sorry, I don’t mean to laugh, but when you said “you think” I was a little shocked. It seemed that Lisa already knew about my feelings about Abby. Liza sunk down on the couch next to me. "Cooper you have lusted at that girl for years and never made a move.” “All four years in college, how many times did you tell me about the emails she would send, or the flirts when she was drunk, or the drunk dials and texts? Now that she is marring Jack, you are hurt you never did anything about it." Lisa placed her hand on my knee locking eyes and saying, “You need to let her know how you feel, before she marries Jack and you live in silence forever.
“I guess I should, I figure a lot of my hesitation has to do with the fact that I have not slept with a woman in 6 months and I'm so plugged up I can’t even focus my thoughts.” Lisa just smiled sliding her hand slowly up my leg reaching my inner thigh. “So…what yours saying is you need some… release?” I blushed slightly as she felt my growing cock through the denim of my jeans. I nodded as she slipped off the bed so that she sat at my feet.
She reached up, unbuttoned the button on my jeans, and then slowly moved the zipper down my pants looking up at me. She pulled apart the side flaps on my fly, “let’s see what we can do about all this pressure.” She reached into the small cloth flap of my boxers she wrapped her hand firmly around my penis taking it out. In her most playful tone, she said, “Well, well, well, what do we have here?” Laughing she reached back up grabbing the waistband of my jeans and pulled them down swiftly to my feet.
Getting a better grip on my cock, she started to work my shaft up and down, gently licking the tip of my dick sending a jolt of pleasure through my whole body. She started to rock her hand up and down my shaft gently kissing the head. She moved her head to take me inside her working her mouth and her hand together. She pushed her tongue around my cock, making sure to get all my pre-cum. After a few minutes, she slid off my cock and took my balls in her mouth. She took each one individually looking up at me while she did. She spread my legs wider with both hands then leaned in applying pressure with her closed lips allowing my penis to part her lips. She slid all the way down and then all the way to the head again. She repeated this for 5 or 6 strokes until I could not hold back anymore and looked around for a towel. Lisa could always read my mind, as I was looking she slid off my dick and said, “you can go in my mouth, ok?" She went down again this time holding the position and I blew my load, blasting everything I had into the back of her throat. She lifted off me holding her mouth close sucking every bit of wetness from my slowly softening dick.
I was amazed; I never remembered her ever swallowing before. “That was a lot of fun, and I think it may have helped me with my um…thoughts.” She kissed my soft penis and pulled my pants up as she stood up. She went into the bathroom to clean up. After she was done in the bathroom, she walked back over to me leaning in to my ear and taking my hand in hers. She placed my hand on her right tit and whispered, “I hoped that helped sweetie, try to talk to her, tell her how you feel."
Chapter 4: Talking to Abby
Leaving Lisa’s room, I felt better, knowing I had to talk to her about my feelings. When I got down stairs, I found Abby sitting alone in a reading chair looking at a book on economics. She looked up smiling to say “Hey!” “Jack went out to get some food so we are going to eat in like an hour if you want to do something until then?” Many thoughts crossed my mind at that moment, including “Yah, I love to rip your clothes off with my teeth and make you squeal like a pig.” Of course, what came out of my mouth was stumble of nonsensical words. I walked to the chair next to her grasping her soft hand firmly in my own.
I breathing became labored as I tried to sike myself to ask a question that had been on the tip of tongue for years. “So, I wanted to talk to you about something.” “I know you and Jack and getting married soon and I wish you both the best, but I think it is important to understand that I have very, strong, feelings for you.” I started to breath heavy, thinking that I had just said the one thing that could ruin our friendship.
Abby looked up, then stood up, all in silence, her face twisted in a half angry, half comical face then said, “You're a fucking idiot.” “You waited until now to fucking tell me this?” “You realize that I have been waiting for fucking years for you to say something?” Her face and tone of voice growing less comical and more angry, “What about all the years of signals, all the years of fucking texts and flirts, and throwing myself at you." "God damn it Cooper!” “Do you realize every time my husband takes me from behind I imagine that it's you." "I spent three years in college thinking about would my life would be like if we got together!" “This is fucking crazy, you just can’t come over hold my hand two fucking weeks before the wedding and tell me that shit, you can't it’s too God damn late!”
I was shocked I was not oblivious to her feelings in college but all this time she was the one waiting for me to make the move." I took step back “Ok, so I feel like an idiot now.” “Look don’t marry him, give me a shot, we can make this work.” She laughed angrily saying, “I have to marry him, I’m engaged, and I can’t go back now.” Lowering her voice and sinking back into her chair looking like she was just emotionally beaten to death as she held her head in her hands. I walked over touched her shoulders and she did not resist. “Please…I have been a fool, but I need one more shot.” She looked up placing a hand on her chest. “I have such strong feelings for you that on some level, I think I want this, but this is too damn late.”
Chapter 5: The Deal:
Still looking into her eyes, I dropped to my knees speaking softly, remembering that Lisa was right upstairs, but knowing that she probably herd everything. “I will make you a deal.” “You meet me 2 am in the morning after everyone is in bed.” “Slip out, don’t wake Jack, there is a hot tub out back meet me there.” “I think we need to do something that is going to get a lot of emotions and unanswered questions out in the open.” She looked down at me placing a hand on the back of my neck. “If you promise to never bring this stupid shit up again, I'm willing to talk." “You have to understand, if this happens it is a onetime thing, understand?” I nodded trying to force back a smile that I’m sure she would not want to see. I stood up leaning in to give her a hug and in my surprise; she leaned in and kissed my hard on the lips. She then leaned back draped her arms around my neck, “I want you to go now and I don’t want to see you until tonight.”
Chapter 6: Me and Abby
That night I found my way through the dark, by the light of my cell phone. As I rounded the back of the house my heart was racing and it practically exploded when I saw the hot tub and Abby standing next to it dressed in a bathrobe, barley covering her black bra and panties.
She turned when she heard my steps “so you ready to do this?” She asked. I walked to her and kissed her. She stepped back sliding her robe off her shoulders letting it drop to the floor. Her figure was more perfect then I could have imagined, not a beauty my media standers but a gem in my book. I pulled off my white t-shirt, and she got close to me kissing my chest. I wrapped my hand around her waist pulling her close, as she reached down with her right hand and pulled my sleep-pants from the waist until they fell to the floor.
She came back up to meet my eye line and kissed me again this time harder and on the lips. She rolled her tongue in my mouth and my mind slipped from reality and into a world of pure bliss. She stopped kissing and leaned in closer to me “I have always wanted you." I held her closer “I thought you just thought of me as a friend, not as someone you could date.” “I can’t believe I did that to you Abby, I was a prick, I'm so sorry.” She stopped kissing me and dropped slowly to her knees.
Standing looking down at her as she looked up at me was intoxicating. I stood in my loose fitting boxer shorts now pushed away from my body due to my rock hard penis. “So speaking of pricks let’s see what we are working with.” She pulled down my boxers from the bottom and a smile came over her face. “God damn it, I don't care about size, never have, but damn it, Cooper, to think I could have been getting this dick for all those years, I'm pissed.” She did not hesitate quickly taking it in her mouth humming with glee.
She slid her lips off my shaft almost as quickly as she had taken it. Standing to turn the hot tub on then returned to her position at my feet. Without words she grabbed my cock and inserted it again, working her hand and mouth in rhythm up and down my shaft. She reached behind her back with her unoccupied hand to release her bra exposing a set of pear shaped breasts with hard erect nipples standing at attention.
I could not wait to touch them reaching out immediately and grabbing her breasts, my cock still buried in her warm wet mouth. She moaned in pleasure as I did and backed off my cock again this time to beckon me with her finger pointing me towards the hot tub. “Get in the tub, its fucking freezing out here!” "I would rather we finished." "Do you want me to suck your dick or do you want to fuck me?" I could fight that question, I quickly climbed into the hot tub and Abby followed pulling off her underwear in one fluid motion as she hit the water. I looked at her body quickly slipping into the warm water and her natural tits resting slightly above the water before sinking in below the water. “You look beautiful Abby.” She winked and swam over to me stopping just a few inches away.
She reached down and grabbed my cock moving her hand up and down before straddling me and inserting my cock into her. She leaned in kissing my neck moving her body in a slow rocking motion as I leaned back in pleasure. She looking into my eyes and we held to gaze both of us saying without words that we were happy together. I placed my hands at the small of her back as she continued to rock up and down the water splashing in rhythm as she did.
When we had gone at it for an hour I was close to popping. Abby seemed to sense it and she slowed her rhythm, "You like it slow baby?" I squeezed her ass hard in agreement. We went on like that for what felt like an eternity, and she leaned in to my ear whispering, “Did you know that I was a diver in high school?” “That means I can hold my breath for a really long time.” She smiled and reached down taking my cock out of her and went under the water.
She inserted in her mouth from under the water and stayed for an impressive amount of time. She came back to the surface and twisted her body raising her ass and slapping it gently saying, "Come on fuck me Cooper." I got into position and mounted her from the back inserting myself into her pushing in deep. We moved together like one perfect being, me pushing in, her pushing back. I kept watching her hair toss and her tits bounce dangling just above the water. I kept pushing harder enjoying the sound of the water as we made waves and her muffled moans and as she took my whole dick inside of her.
She turned back to face me and said, “I’m loving doggy, but I don't think I can hold this position." “I brought down some towels to dry off with, let's lie out on them." We both got out of the hot tub and quickly walked over to the blankets and lay on the floor next to the hot tub. I looked up at her as she lowered her self to lie beside me. "You are so smart to bring some blankets down with you.” She just kissed me and climbed back on top of me straddling me resting her crotch on my neck.
She worked her way up to my face resting her mound on mouth. I took her clit in my mouth and sucked gently. I pushed my tongue into her opening, swirling it around. I kept taking her pussy in my mouth working my jaw her hips rocking up and down on my mouth. I ate her more then 10 min till my mouth felt like it was going to fall off.
She lifted off me and worked her way back down to my waist swinging her legs out behind her so that her head was hovering just above my cock. She moaned a happy eager moan, before taking my dripping wet cock into her warm mouth. She moved up and down on my shaft slowly taking brief moments to rise off my dick in order to kiss my head and lick me from balls to tip. She smiled at me after awhile and turned herself to sit in the cowgirl position. I reached up to grab her ass, steadying her and she started to rock her body up and down again, working faster as she went. She leaned down kissing me deeply as she rocked and I kissed her back.
After about 20 minutes of more fucking, I was coming close to climaxing again. I gripped her neck bringing her bouncing to an end I kissed her once more, “I am going to cum!” She did not answer me but instead pushed herself down so that my cock was in the deepest it could go. Her mussels constricted grabbing my cock and she yelled out having an orgasm.
As she came out of it and back to reality she started to rock her body again. "I have not had an organism like that in ages." I tried to tell her I had to cum but I did not get the words out, “I have to…” she interrupted me, “Fuck me until you cum, you bastard, I’ve never cummed that hard before. “But I don’t want to cum in you, want me to pull out right?” She struggled to form words as she entered into another orgasm. “I’m… on… the… pill.” She cummed again, her muscles contracting grasping my cock, her pussy releasing a flow of warm, wet, juices dripping down my cock.
I held on to her ass trying to keep from cumming to let her finish. Her head tossed back and she pushed down again “O my god, I’m fucking cuming again!” She started to yell, at first at a low volume but then loud enough that I had to cover her mouth. I was closer to cumming with every thrust of her pelvis, giving one last push hard and deep into her wet pussy. In one, perfect moment I cummed hard into her, every fantasy that I ever had coming into reality.
She collapsed rolled off me and rested next to me placing her head on my chest. She pulled a bi beach towel over us and slept instantly one hand in my hair the other around my cock. She woke a few times in the night to tell me she loved me and then went back to sleep.
We spent the night sleeping outside in the night air; waking up I saw Lisa standing is the doorway that lead to the hot tub looking at us with a smile. I panicked and woke Abby, but as Lisa approached, I realized she was only there to help us. Long story short, Lisa is the coolest person in the world. She helped Abby into the house and into a shower, me into my room, then picked up the clothes and left them in my room where they would be safe.