I first met Olivia after Cindy and I had been dating for almost a year. Cindy was very protective of her after having had bad luck with different men that she dated in the past. She did not want Olivia becoming attached to anyone and then having to suffer from the break up. Things were headed in the right direction with us and she finally allowed us to meet. When I first met her, she was young with a flat chest, cute little butt with a beautiful face. We have all seen little girl’s on TV modeling clothe or some other product and we all know why she was picked. That’s how cute she was.
As time went on, we started spending more time getting to know each other. As a “family” we would go out to the movies and then afterwards for ice-cream. I started realizing that she was a pretty cool kid. I would stay over a few nights a week and she would come out in her pajamas to kiss Cindy goodnight, then she would sit on my lap and kiss me on the cheek. I was not sure how to react, so I would go with the flow and kiss her back on her forehead. Cindy seemed to enjoy that as she would be smiling. After several weeks of this, she started giving me a quick peck on the mouth as my goodnight kiss. Cindy’s response to this was “I think someone has a crush on you.”
Cindy and I continued dating for the next few years. We continued taking Olivia out with us to spend time with her. And yes, she continued giving me a peck on the mouth at bedtime. I was totally in love with Cindy and soon I asked her to marry me. She said yes and we started making plans on moving in together. What drew me to Cindy was her beauty and brains. She was a 5′ 8” tall (most of it legs), flat tummy, full C cup breasts with a bubble butt that looked perfect on her. She was biracial (her father English and her mother Jamaican) with black hair and striking blue eyes. She was 35 and I was 30. Her only concern was if I was ready to be a step-father to a 14 year old. That would put me at 16 when Olivia was born.
We were lucky to find a house that was right smack in the middle of both our jobs. In the morning, she would head east and I west. The house also came with a pool. Soon after moving in Cindy got a promotion at work, but it also required that she travel twice a month. She would often fly out early Monday morning and be back Wednesday night. This was her ritual every other week. By this time Olivia had started developing and would prance around the house in her little panties with a camisole as a top. I actually started developing a little crush on her. She developed little A cups with her nipples driving me crazy sticking out. This did not last long. Cindy told her that was not appropriate and that she needed to wear proper pajamas. However, when Cindy was away on a trip, she would go back to panties and a camisole, She was certainly turning into a little flirt, asking me to pinkie-promise not to tell her mother, with a sexy smile. That was a promise I was certainly willing to keep. Again, a young girl running around in little panties. Who’s going to say no?
As time went on, she also started wearing tight cotton shorts that showed off the nice bubble butt that she was continuing to develop, same as her mother. Often times when we went out and they were walking in front of me, I couldn’t decide who had the nicer ass. I remember us having brunch at a diner one morning when Olivia excused herself to go to the restroom. Cindy caught me staring as Olivia walked away, asking me “Are you checking out my daughter?”. I was caught red-handed and stalled, not knowing how to answer. I was saved by the waitress bringing us our food. Olivia soon returned and the subject was changed. Around the house, I would often catch her laying on the sofa, wearing her tight cotton shorts that showed the bottom part of her ass hanging out. Fuck that drove me crazy! Stroking my dick in the bathroom and thinking of her ass had me coming in seconds. What the fuck was wrong with me? This was my fiancees daughter.
Most pretty girls are popular and Olivia is no exception. I suppose having a house with a pool also helped. As summer approached, she asked if she could invite her friends over. Cindy and I discussed it and decided we were okay with it as long as there were no more than five kids at a time. We did not want wild parties all the time.
More often than not it would only be her with four other girls. They would lay around getting a tan and not bother jumping into the pool. On a day that her mother was on a trip, I was peaking out the window and noticed that one of her friends was wearing a thong bikini with a gorgeous ass and the strings to her top undone to avoid tan lines. I unconsciously started rubbing my cock, wishing I could see more. After a few minutes, I came up with an excuse and decided to get a closer look. I was shocked when I stepped out the door and realized it was Olivia the one with the nice ass in the thong laying on her tummy with the strings to her top undone. I quickly excused myself and went back inside. Olivia came in a few minutes later with a scared look on her face begging me not to tell her mother what she was wearing. I told her I would not say anything, but she needed to be more careful. She asked me to pinkie-swear, while giving me a longer than normal peck on the lips and saying “Thank you daddy.” Yes, I went back to spying on her through the window while jacking off.
Another time, towards the end of summer, she came into the house and asked me for a favor in her sweet, sexy little girl voice, asking that I not step out to the back yard. I asked what was going on. She explained that summer was coming to an end and they wanted to get a tan with their tops off. I told her that I promised not to go to the backyard for the next hour. She asked that I pinkie-promise her never to tell her mother. That promise was also followed by a long kiss that was becoming the norm. The thought of knowing that her tiny breast were on full display had me wanting to look out the window. Once again I found myself cumming on my hand while peaking out the window. All five girls were topless cuties.
By the time she reached 16, Olivia was a fucking knock out! Boys were all over her and she was going out on dates every single weekend. I recall feeling real jealousy when Cindy informed me that she needed to put Olivia on the pill. She explained that her daughter had a close call recently and she was not ready to be a grandma. My jealousy was based on knowing these boys were enjoying that sweet ass of hers. The sweet ass that I got to see around the house with her prancing around in her short shorts and even worse, in her panties, when her mother was away on her trips. Yet, I was not allowed to touch.
Life hummed along, with Olivia showing me her delicious ass and me fucking Cindy, dreaming it was Olivia that was under me, on top of me and in front of me. It was Olivia’s lips that were sucking my dick and Olivia’s pussy I was making love to with my mouth. Cindy certainly had no complaints.
One day, Cindy came home explaining that she needed to attend a Conference over the weekend that would require her to fly out on Thursday and not return until Monday night. She asked if Olivia and I would be okay. I assured her that we would and that she need not worry. However, the only thing I could think of was Olivia walking around the house half naked in her new sexy come-fuck-me panties. By this time, on one of Cindy’s prior trips, I had taken Olivia to the mall with the pretense of buying shoes. While there, she explained she also needed to buy new underwear. When we walked into Victoria’s Secret, I was not sure on what to think. She grabbed a few ***********ions and stepped in to try them on. While the cashier was ringing us up, her comment was “I’m sure your boyfriend is going to love these” while looking at me. I stayed quiet.
When we were done, we stopped at the food court for something to eat. I couldn’t help myself and asked her “Do you think your boyfriend is going to love them?” She responded with a smile on her face “She thought you were my boyfriend. You’ll need to tell me if you like them next time Mom leaves.” I was was dumbfounded and not sure on how to answer. On Cindy’s very next trip I found out that I did like her new underwear. I also found out that she had purchased a teddy with matching underwear she occasionally wear around the house in the evening. This girl was playing with fire and I was going to get burned.
The day Cindy left, I asked Olivia if she was up for dinner Saturday night. She had previously mentioned having made plans with ther friends on Friday night. She asked what I had in mind and I told her that it would be nice if we dressed up and went to ‘Di’Amato’s’. It’s a restaurant that has a nightclub right next door. The cover charge is included with your dinner. Unfortunately, I explained she was under 21 and would not be allowed to enter.
Come Saturday morning, I came into the living room with my new camera. It had arrived Friday and I was excited to play with it. Olivia was already in the living laying down, playing on her tablet in her camisole and a new pair of panties that I bought her at the mall. Very little material Fuck!
I started pointing my camera around the house getting familiar with the focus and the camera’s functions. At one point, I pointed the camera at Olivia and asked her to smile, she turned her head and stuck her tongue out. We both started laughing. I continued taking pictures around the living room, but I just couldn’t help myself. I thought I was being sneaky taking quick pictures of her sweet ass when she was so focused on her tablet. I started noticing that this little girl on the couch was starting to slightly open her legs, exposing her sweet pussy more and more. Before long, I was blatantly taking pictures with her not saying anything.
We were both startled when my phone rang. I immediately dropped my camera, my heart started beating a million beats per minutes and she quickly closed her legs. Was she aware of what she was doing? Was she doing that for me?
It was Cindy calling to check in on us. After assuring her that everything was fine on our end, we talked for a bit about her conference and then hung up.
After that, I went to the bathroom. The pictures of Olivia’s young ass and pussy had me cumming in 10 seconds. When zooming into the picture, I could swear her panties were wet at the crotch. Nonetheless, I avoided being in the same room with her the rest of day. I just couldn’t trust myself to not do anything that would ruin my relationship with Cindy. I ran a few errands, fixed the leaky shower head, did other small repairs around the house. Before I knew it, it was 6pm and our plan was to leave by 8pm with reservation for 9pm. Olivia announced she would be leaving to her room to get ready.
A few minutes after 8pm, she walked into the living room where I had been waiting for at least half an hour. If my life was a cartoon, I would be the wolf who’s jaw drops to the ground, his tongue rolls out and he bangs himself on the head with a mallet. She looks hot! Smoking hot! It was as though she had just stepped of the stage at a beauty contest during the evening gown event. She asked “How do I look” while she slowly turned around. Her hair and makeup looked professionally done, with succulent full red lips, gorgeous tits, and the bubble butt that had been driving me crazy for some time now, all while wearing one of her mother’s evening gowns. A backless red dress that went down to her ankles. She was slightly over-dressed for our dinner, but I was not about to say anything. She broke my stare by stating “I will assume you approve from the look on your face.” We were ready to go. I opened the front door and allowed her to go first, catching a glimps of her sweet caboose as she walked out. We walked to the car and I opened the door for her. The way she was looking made me want to treat her like a lady.
We pulled out of the driveway and we were soon on the freeway. “Do I really look nice? I wanted to look nice for you on our date” she said. I told her she looked great! She turned a bit to her left and smiled while asking me “Do I really look good?”
“Yes”
“Do I look sexy?”
“Uh…yes”
“Do I look hot?”
“Uh…maybe.” Was she trying to get me in trouble?
“If you weren’t with mom, would you want me as your girlfriend?”
“Uh…maybe” What was I supposed to say?
“Good!” she giggled “Tonight it is only Tom and Olivia, boyfriend and girlfriend…..Tonight, I’m yours.” She said the last three words in a very low, sexy tone. She turned to look forward while holding my hand and interlacing our fingers, same as she has seen her mother and I do many times in the past. After a few minutes I heard her say “Babe.”
I gave her a ‘are you talking to me’ look. Again, she says “Babe.” Oh, I guess we are going with the pretend boyfriend/girlfriend game. “Yes?” “Does my ass look good in this dress?” “Uh, uh…uh, uh…it looks very nice.” What I really wanted to say was ‘fuck yeah. I definitely wanna tap that ass.’
We soon arrived at the restaurant and pulled up to valet parking. They opened both our doors and she was helped by one of the attendants. The look on his face was priceless. She certainly did not look her age. As we walked to the front door, she grabbed my arm and wrapped it around her, with my hand landing around her waist. I was loving it! We checked in at the front desk and were informed our table would be ready in 15 to 20 minutes. After about half an hour, we were escorted to our table. The young man that seated us seemed new. He asked for our drink orders. I asked for my favorite, an old fashion and Olivia ordered a glass of white wine. I assumed with the kid being new, he was nervous and forgot to ask for ID. Plus, as I previously stated, she looked a older. When he left, I asked what she was doing. She said this was a date and besides, it wasn’t like she had never had wine before. Cindy, on a few occasions, had allowed her to have wine at dinner.
We were talking and laughing and having a great time at dinner, when I suddenly felt her playing footsies with me. I asked what she was doing and her response was “playing footsies with my boyfriend” I reminded her that I really wasn’t her boyfriend and her response was “Tonight you are.” We continued our dinner and conversation – she also continued playing with my foot. When the waiter brought us our receipt, he asked if we would be visiting the club next door, with Olivia quickly responding “Yes.” We were escorted to a special door that connected the restaurant to the club next door. We came to find out that they were owned by the same owner. With no bouncer at the special door, we got in very easily. We went to the bar and ordered another round and found a tall table to stand at; again, she grabbed my arm and put it around her back wit my hand on her waist. We were soon on the dance floor and I had the biggest hard-on of my life with Olivia dancing and grinding her ass on my crotch. With her outfit and dance moves, I am sure I was not the only one having trouble walking. It was soon followed by a slow song and I was feeling her tits pressing hard against my chest and her pelvis pushing against mine. How could she not feel rock hard cock in my pants? She tilted her head and put her lips on mine. Oh shit, I knew I was in trouble.
We continued dancing throughout the night and having a great time. She would kiss me here and there but never really a full make out kiss. I was loving it and started relaxing. I was enjoying our pretend date and started feeling like she really was my girlfriend. At one point during a slow dance, she once again started kissing me and soon we were making out like a couple of teenagers – if only the people around us knew that one of us really was. I was enjoying myself, she really is a great kisser. When I came back to reality, I pulled away. She brought her mouth to my ear and said “Tonight I am yours. Kiss me”. I surrendered to her request and continued kissing her. I am sure the alcohol played a part in me letting down my guard down. With the sensuous kissing, how was this night going to end?
It got late and I suggested we go home. She agreed and we were soon out the door, once again with my hand down and around her waist. Fuck she felt good! As we waited for the valet attendant to bring our car around, the kissing continued, with her always initiating the kiss. What was happening? How was I going to stop this? With a hot young lady all over you, would you want to stop it? I decided to enjoy what was happening and worry about it tomorrow morning. In the car, on the way home, she calmed down a bit and told me thank you for the date, telling she was having a great time. Arriving at home, we drove into the driveway and she did not get off the car until I came around and opened the door for her. She reminded me that the date was not over.
Entering the house, she asked if I could grab my camera. She wanted me to take a few pictures of her in her mother’s elegant dress. I walked to my bedroom and while I was grabbing my camera, she stepped into her bathroom to touch up her make-up. My god, she is fucking beautiful! She started posing in different places around the living room. She looked sexy and my cock was throbbing, begging to be free. She would sit at the couch with her legs crossed, looking very elegant. Nice, innocent looking poses – at first She then stood by the doorway leading to the hallway and stood sideways, with her face turned to me, with her side profile highlighting her succulent bubble butt. These poses were getting sexier by the minute, with her showing more of her beautiful legs through the slit on the side of her dress. By this point, I was done and needed some comfort. I excused myself to change into a t-shirt and shorts.
When I returned, I was definitely not expecting what I saw on the couch. Olivia was laying there on her tummy in her satin camisole and panties, identical to how she was dressed this morning. She asked if I was ready to continue and I told her I did not think it was a good idea for me to be taking pictures of her dressed that way. I was speechless when she answered “Isn’t this what I was wearing when you took pictures of me this morning? Don’t you like my ass in these panties, babe?” I hesitated for two seconds and then pointed my camera towards her and started clicking away. Again, she started spreading her legs, with me knowing that this time she was doing it for me! She kept looking at me while her left hand reached back and slowly started caressing her ass, while giving me bedroom eyes and slowly licking her lips asking “Is this what you wanted?” She then dropped to the floor, with her ass up in the air and her head on the floor turned to the side. Same as any girl would be while getting ready to be fucked from behind. “Babe, does my ass look good?,,,,,does it?” She was mesmerizing and I owed her the truth. “Oh yeah, your gorgeous ass looks very good.” She then asked “Don’t you wish Mom dressed like this for you?” I could only answer a simple “Uh huh.” Her response was “Well, that’s what you have me for, to wear these sexy panties for you.” By now she had turned around and was slowly crawling on all fours towards me with her top hanging, showing me most of her tits and part of her areolas. I felt like some sort of prey as she approached me. I was dumbfounded with nothing to say other than to enjoy her beauty. She approached me and slowly got up onto the sofa and straddled me.
We started kissing as she started grinding her sweet little pussy on my cock. The only thing separating our genitalia was her panties and my shorts. In the name of comfort, I had not bothered with any underwear when I changed. There is a kiss to say hello or goodbye and then there is a “I want to fuck you” full make-out kiss. That is what was happening between us. She was shoving her tongue in as far as it could go while grinding her pussy hard on my cock. I assumed this was as far as we would be going and I was more than happy with it. Her young, hard, smooth body felt amazing in my arms as I kept feeling her up and down from her flared hips to her waist and up to her shoulders.
She started telling me that she had a crush on me when she first met me as a little girl. “When I started kissing you good-night, I always wished that one day you would kiss me back. But you never did,,,..until tonight.” Once again we started making out, with her tongue deep down my throat. Then she asked if I remembered when she first asked me not to go to the backyard because she would be tanning topless. I said I did. “As I laid out in the backyard, especially when I was alone, I fantasized that you would come out and put my little titties in your mouth.” As she said this, she grabbed the bottom of her camisole, pulled it over her head and sat there on my lap with her gorgeous, young naked B cup breasts mere inches from my face. She cupped one of her breasts with her hand and fed it to me. “Suck it, baby. Please suck my breast.” How the fuck could I say no?!? This goddess is straddling me topless, only in her panties, asking to suck her breasts. Yes, I did exactly what any straight man would do.
As I was enjoying her breasts, sucking them hard as if expecting milk to come out, she started moaning loudly, telling me how long she had been dreaming of this, telling me “Please don’t stop, please don’t stop…your mouth feels so good.” She allowed me to suck on them for awhile before she started sliding down until she was on her knees looking up at me with her gorgeous eyes. There was no need for words, she simply grabbed my shorts at the waist and started pulling them down. Subconsciously, I lifted by butt so that she could easily pull them down. She had a little trouble with my stiff cock causing her a bit of an obstacle. Of course she did not let that stop her. She reached in, pushed my cock down and continued pulling down my shorts. She did not stop until they were completely off. At this point, I thought to myself that everything would be okay because there was no penetration. Oh, the lies we tell ourselves.
She grabbed a hold of my cock and started stroking me slowly while telling me “You know, when I stand by your door, hearing you and mom fucking, I dream that you are telling me, not her, to suck your dick, telling me to put your big fat dick in my mouth…..,,say it, say it! Tell me to suck your dick!” She kept stroking me, waiting for me to respond. I was not sure what to say. She then repeated herself “Say it, damn it, tell me to put your fucking dick in my mouth and suck it!!” At this point, my dick was controlling my mouth. “Olivia, suck my dick. Suck my dick, baby.Open your mouth and suck daddy’s cock” She immediately brought her lips down to my dick and started licking the head, the whole time looking me in the eyes. She held my cock while opening her lips and lowering her head. My god, it was my wet dream becoming a reality. It was actually Olivia and not Cindy sucking my cock! Compared to mom, she was not as skilled. However, her enthusiasm certainly had me close to cumming. She must has sensed it, because she took my dick out of her mouth and told me another dirty little secret.
“You know, this morning when you were taking pictures of my ass, I really wanted you to reach out and pull my panties down so you could stick your dick in me and fuck me.” While she said this, she stood up in front of me and reached out for my hands. She pulled them to her hips, stuck my thumbs into her panties waistband and started pushing down. I caught on very quickly and pulled them down the rest of the way, helping her step out of them. When her panties revealed her little slit to me, her pussy was perfect. Her lips looked wet and gave off a sweet aroma of youth. “I wanted you to see my smooth little pussy” she kept talking as she once again straddled me, grabbed my cock and started rubbing my dick back and forth along her slit. “I shaved my little-girl pussy so that you knew exactly who you are FUCKING” The moment she said the word ‘fucking’, she started going down and my dick was very quickly half way into her vagina. My god, her pussy fit like a glove two sizes too small. Her sweet young pussy was so tight. “I want you to remember that this is not mom’s pussy, this my little pussy.” We concentrated on fucking, with her on top having all of the control. I took my shirt off and put my hands one her sweet, tight ass, helping by pushing her up every time she came down while continuing to enjoy her breasts in my mouth. I kept alternating, getting a mouthful with each one in my mouth. “Your big hard cock feels so good. My god, it feels so fucking good the way your cock is stretching me. Now that I’ve had a man’s cock, your cock, I can never go back to the boys in school with their little dicks.” She started moaning louder and louder amd bouncing harder and harder. She kept telling me to fuck her harder and harder and to make her a real woman; telling me how much she loved my dick. Before announcing that she was cumming. I felt her shaking, her was body was trembling. I thrusted my cock harder up into her sweet cunt. “Oh fuck, that feels so go, baby…..I’m cumming, oh my god, I’m fucking cumming!! She trembled a bit longer before it came to a slow end. When she stopped shaking, she put her mouth next to my ear and told me “my pussy is all yours now….only you get to fuck this pussy!!”
I told her to get back on the other couch with her ass in the air. She did as she was told. As I positioned myself behind her, I couldn’t stop admiring her tight body. A beautiful smooth fresh body that only a young lady can have with her breast hanging, her taut stomach and her gorgeous ass and her shaved, cute little pussy. It drove me crazy remembering her telling me that she shaved her little-girl pussy so that I knew exactly who I was fucking. She wanted me to know that this was not a woman’s pussy, this was her little girl pussy. There was no way I would ever forget who I was fucking.
As I stood behind her, I grabbed my cock, lined up to her cunt and proceeded to slowly enter her. I wanted her to enjoy every inch as we slowly became one. Even though we had just fucked, her pussy felt so tight going back in. I looked down and saw my dick entering and exiting her cunt, the same view I had enjoyed many times before while fucking her mother. I was fascinated at knowing that this little bitch was mine, her cunt was now mine, her tits and her full luscious dick-sucking red lips were also mine. She had planned this whole night in order to give herself to me. To surrender her body for my pleasure.
As I continued fucking her from behind, she asked me “Do you like fucking your little girl, daddy? Huh, you fucking pervert, do you? Does my pussy feel tighter than Mommy’s? Does my pussy make you want to come?” Her words and her pushing back were driving me closer and closer and I couldn’t hold back any longer. I thrust forward and kept my dick deep in her pussy as I came like I never had in my life, not even when I first had sex with Cindy. “Oh my god, daddy! I’m cumming again, That feels so good, I can actually feel you shooting your cum in my pussy!” She quickly turned around and took my dick into her mouth, trying to suck out as much semen as possible. I soon asked her to stop, telling her my cock to getting too sensitive.
We were spooning on the couch, not saying anything, just holding each other. How the hell did I get so lucky?!? She then spoke up “Thank you for tonight’s date. It was better than I could ever imagine.” We both quietly drifted off to sleep.