Bareback Sex With Escort

    Wright Thiesen
    By Wright Thiesen


    I’m a 26 year old virgin and fucked my first escort
    Let me just say I’ve been very very reclusive for the past couple years and smoke a lot of pot.

    I was in my room smoking weed, as usual, and I had been already been interested in visiting escorts. However I never had the balls to partake. A few months prior I did go see MPA’s(rubn’tug) three times total (All within the limits). Previously to that I had no physical contact with any woman at all, aside from the couple times I went to strip clubs. I just feel very undeserving of a woman’s affection and always think she can do better than me.

    I was actually about to go to a massage parlour again because they were having a special. But for $20 more I figured I could have the option for more fun with an escort. I had an escort that I had been wanting to see for a while, as she seemed extremely safe(CBJ, no kissing, no DATY, etc.) which I liked. As well she was blonde and tall. I msg her and ask her if she’s free for 10:30pm. She gives me the intersection and rates. Now at this point I’m absolutely petrified. Literally my heart is racing and I’m anxious as hell. And I haven’t even come close to doing anything yet, lol. But I tell myself, that I’m only going to use her for a massage and release. So I put the right bills in my wallet. It’s about 9:15pm so I use this time to smoke as much weed as possible till 10.

    Now the weather outside was weird today, it was snowing at the end of march, previously in the year we had no winter at all. And today was the one day it freak snowed. dick sucker xxx cams took it as symbolism for ending my cold dry spell. I drove to the motel and texted her when I was parking. She gave me the room number and I knew it was time. As I walked into the reasonably well maintained lobby, no one is at the desk, and the elevator doors just open to invite me in. I walk in and push the button. I knock softly on her door, it opens moments later, where she is not directly in front of me but sort of behind the door. I see she is topless with only a g-string thong on. Lol, she closes the door behind me. Looks wise, I don’t really know what I was expecting. Guys had rated her as one of the hotter escorts but too restrictive for their tastes. For me I would rate her about a 6/10 facially with make-up. Her body was what I was expecting, curvy and juicy ass.

    I’m also still very high and try to keep composure. We shake hands and she goes towards her bed, tell me to leave the money on the dresser and wash my hands in the bathroom adjacent to me and get undressed. I comply and she says she going to give me a back massage. I thought great, as this was at least familiar to me. xnxx porn gives an okay back rub for a few minutes. I don’t like laying on my stomach as it puts strain on my neck, so I ask to have my chest massage. I flip over and she rubs my chest for a bit, I play with her tits and start a bit of dirty talk. Suddenly she goes on like autopilot grabs a condom in her mouth and wraps it around my cock like a pro and is sucking away. Well I’m past the point of no return, I thought. I have a weeks worth of jizz in my balls too, so I ask her to go slow. I start playing with her pussy, and feel that she’s really wet. I ask her to turn around so I can see her head going down on my cock. She has pretty good technique, but I really want to fuck. She asks me what my favorite position is and I stumble and say missionary, she says “me too”. I get up and she lies down and spreads her legs. I’m smiling in my head how easy this is. I slide my dick in her and basically just lie on top her humping away. Eventually Kylie Jenner Nude lose control here and start ramming her as fast as I can and cum hard. I still wanted to fuck but my dick is losing blood. And I tell her “I think I came”. Finally I get a real shred of emotion from her, “you think?!” LoL I’m still so high and she tells me to toss the condom in the toilet and hands me a baby wipe. As I’m cleaning myself off I feel quite ashamed of what I had done. I still had time left too, but was unsure on how to bring it up. I was extremely quiet at this point so I quickly got dressed. My stepsister and her mother moved in with us when she was 3 and I was 13. She was a spoiled brat that I couldn't stand being around. But when she hit puberty and started to become a woman my view of her started to change. But because of our age difference, her being my stepsister and me being married me only admired her from afar.

    After I graduated high school and got married my dad and stepmom joined a nudist resort. After a year or so they invited my wife and I to go with them. Personally I think it was so my dad and bi stepmom could see my wife naked but that's another story for another time. Because of the resort my sister had no problem being naked around me. Fast forward to her senior year.

    We live in a small town and 4 houses away on the same street. Every few months our parents, who are swingers, would go to the resort or camping with friends and my sister would stay with my wife and I. As luck would have it my wife took our kids to visit her family while I stayed home because of work the same week our parents went out of town.

    The first couple days of us being alone together we mainly just flirted with each other witch we had been doing for a while prior to this week. I also sleep nude so in the mornings I would get up and go to the kitchen to make coffee before getting dressed. At night I'd undress before walking down the hall to take a shower. She wouldn't walk through the house naked but there were times she'd have on just her underwear. Just like at the resort we would pretend not to notice the other but I would always catch her checking to see if I was or not and try to hide a grin when she'd see me watching her. When she would take a shower I would go into the bathroom and talk to her. I loved watching her through the semitransparent shower curtain. She is 5'4" reddish brown hair with the light skin and freckles to go with it. She also played sports all year round so she had an athletic hard-body with perfectly round butt-cheeks that just beg to be touched.

    Even with all the flirting and some light touching we had done for a while now I was still nervous about going farther than she was willing and telling our parents or my wife. It was the third night when she was taking a shower and I asked her if she'd like a full-body massage when she was done. She said yes.

    When she got out of the shower I went to my bedroom to get the bed ready. I got the massage oil out and laid a towel on the bed to keep from staining the blankets with the oil.

    A few minutes later she came in wearing a matching black lace bra and thong. The sight of her wearing that knowing she had put that on just for me made my already firm cock get hard and stand at attention. She got a naughty grin on her face when she saw the rise she got out of me.

    She laid face down on the bed. The thin piece of lace that disappeared at the top of her ass and reappeared at her pussy which was also trying to swallow the thin fabric made my cock throb as I got on the bed and straddled her.

    I ran my hands from her hips up to her bra where I unhooked it. As she was removing her bra I grabbed the oil and rubbed it into my hands. When she settled back down I started massaging the oil onto her. Rubbing from the top of her thong to her neck. Making sure to press my throbbing cock against her firm round ass every time. As I massaged her she started to ever so slightly lift her ass to meet my cock.

    After several minutes of massaging her back I moved down so our knees were next to each other and oiled her ass and legs. Putting my knees between her legs so I could get oil on her inner thighs which of course gave me a perfect view of my ultimate goal. With her legs spread her puffy young pussy lids opened just enough to take in the thin lace fabric trying to cover them. While massaging her ass I made sure to do it in such a way to spread her cheeks an expose her asshole being cut in half by the string of her thong. Massaging her legs I would start at her knees and go up to her soft shaved pussy making sure to do it in a way that made her pussy open even more. After massaging both legs in this way it made so lace fabric that was supposed to be covering her pussy now was being devoured by her beautiful mound.

    I told her to roll over. I didn't move from where I was kneeling on the bed. I got the oil proceeded to oil her belly and tits. Her tits are a little more than a handful, very firm and with small pink erect nipples. Spending several minutes rubbing the oil into her belly and tits. But most was spent on her tits. Gently rolling her hard nipples between my thumbs and forefingers. The longer I did this the heavy her breathing got and the more her hips would move. And the wetter pussy got.

    She was laying there with her eyes closed and her mouth slightly open. I gave her breasts a gentle squeeze as I leaned over and pressed my lips against hers. Kissing her for the very first time. Since her eyes were closed it startled her and her eyes opened wide. But just as fast as her eyes had opened her tongue shot into my mouth and she wrapped her arms around me. While we explored each others mouths with our tongues I slid my hands down her body and gently pulled at her thong. For a moment I didn't know if she would let me take them off. Then she lifted her hips so I could get the thong over her round ass. I sat up to get her thong off and expose her pussy that is the same light pink as her nipples. And almost dripping wet now.

    As she lay there with a nervous grin on her face all I could look at was one of the most beautiful pussies I have ever seen. Since I have seen her naked before knew her clit was big enough to poke out of her pussy when her legs were together. More than most pussies I had seen. Seeing it fully exposed I couldn't help but suck on it.

    She gasped, lifted her hips and grabbed the back of my head to press my face into her as I started sucking and massaging her clit with my tongue. While she held my head and ground her pussy into my face I managed to work my sweatpants off. Finally releasing my hard throbbing cock from its prison.

    As she continued to grind and I continued to suck I started to rub her pussy. Using my middle finger I started to gently probe the hole that I've been longing for. Her pussy was on fire and dripping as I continued sucking her clit and finger fucking her. Her moans were almost screams as she continued the grind my face into her.

    I started to put two fingers into her. But could only get two fingers in to the second knuckle?! I thought, "Why is she so tight?". That's when I realized the opening was much smaller than the inside. She still has part of her hymen! She's a virgin and I'm going to take her virginity!

    I don't have a large cock but it is bigger than average according to what I've googled. I'm a cut 7 inches which is longer than average and I can barely touch my thumb and middle finger around it which is thicker than average. "If I can't get two fingers in her how am I going to get my cock in her?"

    I continued sucking her clit as I tried working both fingers into her. She didn't let go of my head but she did stop grinding into me and her moans became heavy breathing with almost whimpering gasps when I'd press my fingers into her. Was I hurting her? I could tell I was a little but she never let go of my head so I continued on. I stopped sucking her clit so I could focus on getting my fingers in her without causing her too much pain. When she was finally stretched enough it was like when you stick your cock in an ass that wasn't stretch first. When the head of your cock pops past the sphincter it tries to suck the rest of your cock in with it. That's what happened. My knuckles popped past her hymen and her pussy sucked my fingers all the way in. She let out a light gasping scream and grabbed my wrist. But instead of pulling my fingers out of her, like I expected her to, she held my in her. Even pressing my hand into her little more.

    She lay there with her head tipped back and her mouth gasping as her pussy was spasming, squeezing my fingers like a vice as it tried to adjust to this new invasion.

    After a couple minutes she got her breathing under control as her pussy accepted my fingers and let go of my wrist. I licked her clit letting my saliva drip onto my fingers to help lube them as I ever so gently started moving them around in her.

    When she got use to my fingers I re-positioned myself to kiss her with my fingers still in her. She stopped me and said, "But you just ate my pussy!" A little shocked all I said was, "So." and put my tongue in her mouth. Which she also did in return.

    While we kissed and I continued to finger her tight pussy my head was swimming with thoughts. She'd had a couple boyfriends in high school but never let them finger her?! Or even use more than one finger on herself?! And never licked her finger while playing with herself to taste her own pussy?! I'm I really about to fuck my sister or is this the best wet dream I've had about her yet?!

    As we continued to kiss and the thoughts continued to swim about in my head she started to move her hips in rhythm with my fingers. It was time.

    We continued exploring each others mouths with our tongues as I pulled my fingers out of her burning pussy and re-positioned myself between her legs. I moved my mouth to her breasts as I took my cock in my hand. Sucking on her nipples while rubbing the head of my cock on her pussy and pressing it against her hole. My fat head wasn't even starting to go into her. It was like there was no hole there. I sat up so I could see her hole and put my cock exactly where it needed to be.

    Even though I had just spent several minutes with two fingers in her it was like she shrunk to the size of a pencil. Taking a firm grip on my cock I pressed hard against her hole. No go. In my head I has screaming, "NOOOOOOO". I continued rubbing my cock on her and pressing my head into her hoping this would be the time it'd go in. This went on for what seemed like forever but was probably only a couple minutes. I was starting to go soft. I couldn't believe I was so close to fucking the pussy I've been longing for so long and couldn't have it. Then it happened.

    The head had shrunk enough to go in. When the head popped in she let out a little scream and pulled away a little then relaxed again. Since all I had in her was the head and I was almost completely limp I leaned over and kissed her while pressing and grinding myself into her. She wrapped her arms and legs around my holding me tight against her as we kissed. Between that and her tight throbbing pussy squeezing the head of my cock I started getting hard again. I was able to slowly work it in as I slowly got hard again. I didn't get completely hard till I was all the way in her.

    Her hymen was squeezing the base of my cock like a cock ring that is too small. Because of how much I had grown while inside her I was afraid the try and trust in and out of her. I could tell by the look on her face I was hurting her. But like with my fingers she held me tight in her. As she kept her arms and legs wrapped tight around me her body twitched and convulsed under mine. With each twitch and convulsion she would let out a mix of moans, gasps and whimpers as the feelings of pleasure and pain swept through her body. Because she was so tight and I had gone in soft and doubling in size one in her pussy was also convulsing trying to expand to the thing that had groan inside it.

    Because of how hot and tight her pussy was and how it was convulsing around my cock it didn't take long before I couldn't hold it in anymore. I had had a vasectomy a couple years earlier so I didn't wear a condom and pumped my load into her. Every time my cock twitched to pump out my cum it would make her pussy clamp down on my cock and she'd let out a loud moan.

    It was like her pussy was milking every last drop of cum out of me. When I finally stopped cumming and her body stopped twitching and convulsing I collapsed on top of her. We laid there for several minutes panting and covered in sweat with my cock still trapped in her twitching pussy. When I was soft again I slowly pulled out of her since I knew she must be sore. Her pussy was still so tight that my cock came out almost dry but when the head popped out my cum poured out of her.

    Because of how sore she was we didn't fuck again till the next night. I was able to get it in her while I has hard but she was still supper tight. The next day we had an idea about when our parents were going to be there to pick her up. I had bent her over the bed and was fucking her from behind when our parents pulled into the driveway.

    She lived at home for the next couple years while she went to the local community college. We would fuck every chance we got. When my wife would be gone overnight my sister would sneak out of our parents' house and into my bed. During the day if I was the only one home she would tell our parents that she is going for a walk. There were several times we all went camping and after everyone was asleep we'd sneak away.


    She tells me to call her again, I thank her and she tells me the back exit is down the hall. As I walk down the stairs I notice it is not maintained at all. It’s like a dark, grimy escape for all the johns that fuck the questionable women operating in that motel. I see symbolism again that this choice of lifestyle is downward-spiraling and degrading to both parties. Although I really don’t want to do it again (with an escort), I feel as if there is a great weight lifted off my chest and don’t have the virgin label on my head anymore.

    But all this time I thought I wanted sex, but in truth, it was intimacy that I had been searching for and will continue to search for
    I just want to enjoy amazing girls. Crazy what sort of journey I've embarked on pursuing this quest.