This story follows up a story I wrote a few months ago.
I’d been in a relationship with Sara for a year before we split up. Sara was fun in bed but public sex was her thing. It turned her on to think we might be caught in the act. She loved fucking in her little red Toyota MR2. I’m six-one so her petite body was the only thing that made it possible. She had places to park all over the DC metro area, but we had car sex mostly in Northern Virginia where we worked.
I remember spending the night at her parents house. I slept in the guest room but in the morning I went to her room, she insisted we leave the door open which was one of her parents rules. She said, “Keep your clothes on then lay behind me on your side and we’ll spoon. I’ll slide my pajamas down and you pull your pants down.” It wasn’t great sex, I’d have liked to tear off her clothes and had her bounce on my cock. Later we went for a bike ride and fucked in a field just out of sight from the bike path, it was fun but really not very comfortable.
Our sex life dwindled after she got an apartment near our office. She complained of being sore after the first week of me dropping by before work to wake her up, and hooking up after work. I was too stupid to realize that she really wasn’t that turned on by normal sex.
She had been my second real relationship and it kind of threw me when she broke up with me. I wasn’t happy with my job, and my Dad had just gone through chemo therapy so I didn’t have anything holding me back from going on the solo cross country bicycle trip I’d always dreamed about. I quit my job and took a train to San Francisco two weeks later. I dreamed of fucking my way across America but of course it ended up being me jacking off in my tent—a lot. When I got back to DC three months later I stayed a couple of nights at Sara’s apartment. I hoped we’d get back together or at least have sex but of course she’d moved on to some other guy she’d met at her new part time job as a Hooters girl. It would have been fun to pick her up from work and go for a drive…
I met Jane, an older woman in my intro to graphic design class. Jane had been to art school so she said she’d help me as I’d enrolled full time in a graphic design program. I was working nights as a bicycle delivery man for Dominos Pizza. Jane liked to ask the dispatcher for special delivery, which should have been fun but was kind of creepy. My fathers cancer came back and I was having a hard time dealing with it all. One night my manager, who thought the whole thing was hilarious, gave me a ticket from Jane’s apartment. Apparently she didn’t realize I was working that night and a guy wearing her frilly pink robe answered the door. When my dad died later that spring I was really was thrown. I quit my job and barely got through the semester. My sister and I decided to keep his house. I’d live there with housemates, and pay my her part of the rent and have a little extra to live on while I got a graphic design certificate.
The first housemate was an older guy from Africa who’d just graduated from college and the other was Mandy. She had just graduated from high school and would be attending one of the better DC Universities. My friend had worked with her as a volunteer for a political campaign in her hometown a few hours from DC. He said she was a mature girl that didn’t want to live in the dorms. I was happy to have someone with a reference and figured once school started she’d be gone most of the time studying or having fun doing college stuff. She was not exactly what I expected. I thought political wannabes were nerds. Mandy was still seventeen but would be turning eighteen in a few weeks. When we met she was wearing a short tight skirt with a Mondrian pattern in classic primary colors, and a loose white blouse which couldn’t hide her ample breasts. I thought she was cute, which might be trouble, but she promised that she wouldn’t be inviting boys over. I was happy to have the rooms rented.
Mandy moved in a few days later and looked for a summer job in DC. I remember thinking of how her breasts looked in her sweaty tee shirt as I jerked off in my bedroom. They were her best feature but her blond curly hair, blue eyes, and delicate features also offset her slightly chunky five-two frame. I was in great shape and cocky. I considered myself to be above her league in looks.
I had a couple of friends over the next night and they were circling her like hyena’s on a fresh kill. I was a lion fending them off. My friend Dan was a shameless womanizer and she was loving the attention. I knew he’d fuck my perfectly good paying tenant without a thought about the consequences to my finances. I don’t remember what I did but I kept them apart. She may have mistaken this for interest on my part. I was determined to keep her in the friend zone, it would be legal and financial suicide.
As a good landlord and representative of Washington I felt it was my duty to show her around DC. Neither of us were working yet and school was out for summer. She went home for her eighteenth birthday while I went to New York to visit a buddy living in Greenwich Village. My friend had spent a year living in Sweden and had a couple Swedish girls visiting him. They weren’t the blonde bombshells I was hoping for, and I returned to DC having not been with a woman for a few months.
Mandy hung out drinking beer and watching TV the evening after I returned from New York. She leaned back on the day bed we used as a couch and teasingly said, “I’m not jail bait anymore,” while putting a hand behind her head thrusting her chest out like a pinup girl. I’m a bit thick so I chalked it up to her being drunk. I couldn’t imagine she’d want to screw up our living arrangement and growing friendship.
The next day we rode our bikes to Georgetown and played tennis on the public courts. She was pretty good and moved well but her bra was not up to the challenge. Her body looked a lot like this girls.. That night we were back in front of the tube drinking beer. I don’t remember what we were watching but at some point she challenged me to wrestle saying she’d taken karate and was stronger than she looked.
I was leaning back against the pillows when she tried to pin me. She was pretty strong, and I was already on my back. When she leaned on me I could feel her breasts press against me. I was instantly hard. She was sliding down toward my erection so I flipped her over to avoid contact. She laughed but then saw my hard cock through my shorts and reached for it.
It was game over, I couldn’t resist anymore. I had too feel those boobs. I grabbed them through her shirt and bra they were definitely more than a handful. She moaned, and gripped my cock through my shorts. I reached under her top, then she sat up and pulled off her shirt. Jesus there was something so nasty about this sweet innocent looking girl and her big pink nipples under the sheer fabric of her lightly patterned white bra. The bra had to go, I fumbled with the clasp while she slid my shorts down. Then I attacked her tits with my mouth while she slid her shorts down. I could smell how turned on she was and it drove me crazy. I looked down and saw her dark red engorged pussy lips slightly spread open begging for my cock.
I slid in in easily, she wasn’t a virgin but she was much tighter than Jane, just super wet. She must have had a lot of built up desire. I threw the big pillows off the daybed and thrust in and out slowly, then sank in deep thrusting hard at the end. She tensed and slid back and pushed me. Jane liked it when I bumped her cervix.
Mandy said, “not so deep.”
“Ok,” I didn’t want to talk. What was I doing? Shit. I almost pulled out and stopped, but she wrapped her legs around me and pulled me in.
I worked faster but not quite as deep. Her boobs were glorious. I watched them move back and forth on her chest, they didn’t flatten out of flop to the sides they stood proud and moved as two independent softball sized globes of flesh with just barely visible areola and those big nipples. It was too much, I came. The whole thing couldn’t have lasted more than a few minutes.
“I have to clean up,” I said as I got off her. my dick was coated in cum and pussy juice.
“Me too,” she said.
I went to the downstairs bathroom while she went upstairs. As I washed my dick in the sink I tried to think of what I would do next. We were both drunk. It didn’t have to happen again. We could still be friends.
Source: reddit.com/r/gonewildstories/comments/3zogd9/more_of_my_misspent_youth