After an already pretty productive week (I had already seen West Point, Fickle Daddy, and Mr Fantastic this week), I was still sexually wanting. My insatiable sex drive needed more of something; more variety, more penis, or more orgasms–just more. This is where House Sitter comes in.
I matched with House Sitter on Tinder and for over a week he would ask me to meet up or come over to the house he was at. These requests would be during the day, right after work, or my favorite time–2am. I am obviously not a huge fan of booty calls, mostly because I am passed out by then and that bed is real comfortable after 10:30 at night. But I digress…When I matched with House Sitter (HS), his pictures made him look about a hard 8, and with his age of 22 I was hesitant if this was going to be a good choice or if I was going to get a “show me ur tits” within 3 messages. What can I say, past experiences can leave a girl leery. HS was very upfront about wanting to meet for what one could only hope and pray was not disappointing sex. Within just a few messages, House Sitter asked for my number so he could share pictures of himself, and that’s when I became the receiver of a beautiful dick pic. When I say beautiful, I mean it looked like it would make Catherine happier than a fat kid on dessert day. With his first invite, House Sitter enticed me with promises of massages. This was incredibly enticing, especially when I know I have the worst back ever. However, life and sleep got in the way.
Meeting up with HS was easier sad than done; I matched with him the Monday and he got straight to the point. I saw Fickle Daddy and Mr Fantastic that following Tuesday and didn’t really need to see three guys in one day, especially since I already had an orgasm with Mr Fantastic. I drug my feet on seeing him in person; this tends to happen when you’re busy with life and already have someone to help with most of your sexual needs. I eventually had free time to see House Sitter on Wednesday afternoon. Before getting ready to head over, I asked him if he had condoms; he did not have any, so I instructed him to go get some (I’m not a condom delivery service.)
He lived about 20-25 minutes from me, so I figured that plus my lazy way of getting everything together before leaving would be enough time for him to literally drive across the street to get a box of condoms. Boy, was I wrong. When I arrived at this fancy house on a golf course, I was greeted by a shiny and new sports car in the driveway (possibly his since there were clothes in the car and looked like a 2nd year senior’s car), House Sitter, and a great dane sized dog at the door. I was in love–that dog was the sweetest and gave the best big dog kisses ever! There was even a second big dog with which to give my all my love to. Yet, all I could focus on were the two dogs in the room, not the pretty damn hot younger gentleman that opened the door for me with a toothbrush in his mouth.
House Sitter was around my height (5’9), dirty blonde hair, blue eyes, and a fit frame. To say he looked like the well tipped bartender of a college town is an understatement. He quickly informed me that he had not gone to buy condoms. I think my expression went from, I LOVE DOGS, to, the fuck is wrong with you, bitch?, real quick. We don’t do sans condoms with a guy that looks like that, ever. That is chlamydia real quick, and I’ve had that enough in my life. I responded to his failure by saying “Well we should go buy those before we start taking any clothes off.” He offered to drive to the store, and I was ready to go. That shiny sports car was made for tiny people with tiny legs. I am tall with big thighs–I did not enjoy the clown car ride to the local pharmacy store to get condoms. Once there, he left me in his car to go procure anti-STD protection. I then texted my safe buddy to let them know where I was and that I could over power HS if needed. When HS returned to the car, he decided to not only flash me the condoms he bought, but also that they had this “fancy” sex oil. He bought the Trojan massage oil; I don’t know how that’s fancy, but it was to him.
Once back to the house, he directed me to the side bedroom he was staying in, away from the adorable dogs sadly. He turned on a side table lamp while I noticed he had thrown a sheet on top of the bed, which he said was because of the dog hair. Immediately House Sitter started to get undressed and asked if I wanted that massage. I quickly responded and said yes and asked how far I had to be undressed for this as he stood in front of me in his boxer briefs. He didn’t respond, so I just stripped down to the panties I had on and laid face down on the bed. HS walked over to where I was on the bed and straddled me with no warning as he poured what felt like half the bottle of oil on my back.
Cold. The oil was so cold and it hit my only ticklish spot–my spine. I flinched and bucked up into him something fierce. He told me to calm down. Don’t tell a woman to calm down when you have her basically pinned down in a strange house with cold liquid running down her back. I assumed the dogs may have saved me in the end, they knew I was their kind. After massaging my back he pulled my panties off not with his hands, not with his feet, no HS went all porn style by removing them with his teeth. How could I tell? He would move them down, kiss me, remove from another side, kiss, and repeat until they were at my knees. While this sounds like it’s leading up to some slippery sex, it led to a lot of massaging of my ass.
Pushing my cheeks together, spreading them, pushing up, pushing down–it was a nice muscle massage if I needed that.
House Sitter was so quick to put on the condom that if I hadn’t seen it afterwards I would have thought he didn’t use one. He wasn’t into kissing and didn’t want me on my knees for doggy, just laying on the bed so he could fuck me that way. Why didn’t he want me in a better position? Probably so he could fuck me between my actual ass cheeks. I didn’t know if I should tell him that that’s not how sex works, but I just laid there. Eventually he entered inside me; his cock was decent sized, but I couldn’t feel it that well from the angle he used to fuck me. I tried to push my ass up into him as much as possible, but it just wasn’t as exciting as I wished. It didn’t take him that long to change positions; he had me roll over onto my back so he could play with my boobs while on top. Not too long after, he came, rolling off of me and getting up to get a towel for me. I asked if we could cuddle, to which he shrugged it as a yes.
House Sitter was not a fabulous cuddle companion, but at least I got some cuddles before trying to turn him on again. Because I didn’t give him head before the first time, I didn’t notice that he literally dunked his crotch in cologne. The smell of men, in forests, and their big beards was really strong on his trimmed pubes. His cock didn’t make me gag, but the smell did. Unlike other men, I wasn’t down there as long as I would have normally been. The second time was not as long as the first round, but at least I got to feel all of his cock this time around.
Once done, he said he was going to take a shower and I said I would clean up and put clothes on. When he came out of the shower (which was a drug out shower, honestly), he was overly surprised to see me still slowly getting ready. My bad, I had to check my phone and respond to work e-mails. I apologized and said I would be leaving shortly. I grabbed my things, kissed all over the dogs, and went on my merry way.
House Sitter reached out to me a few more times before he went back to school/work/wherever he came from. While I enjoyed it enough, he wasn’t really something more than a one night to me. I was also in Houston pretending to enjoy the company of someone with a tiny penis and a horrible alpha male personality.
Lesson Learned: If your gut ever feels weird, it’s probably going to be weird. Also, dogs make or break things, and if he was staying around and they were his, I would have been around 24/7.
The Daring Vagina