I Had to Pay for The Hotel Pt. 01

A little backstory on how I ended up in my situation. My name is Steve and I am 25. I am a college educated guy who works in finance. I really never had much luck with the ladies during college other than a few one night stands. I'm 5'9" tall with a slim swimmer's body. I'm also average in the cock department being around 6" long and average girth from what I've seen in locker rooms at the gym.

I first laid eyes on Rebecca, or Bec for short one night while I was out at a bar. We instantly hit it off and I loved her long blonde hair and green eyes. She was very engaging and we ended up talking for a while before we left and went to a small local coffee shop and talked for a few more hours.

She was 24 and had a totally different history than I did. While in highschool she fell in love with her highschool sweetheart. At the end of her senior year she ended up pregnant so they got married. She ended up working at a local department store and he worked at a manufacturing plant. They were together for a few years and then he surprised her by saying he wasn't ready to be a father or a husband, divorced her and left town. Now all she sees of him is a card at the holidays and on their son's birthday with some money in it.

It was a sad situation but the way she took it in stride and had just kept going amazed me. Everything about her was exactly what I had been looking for.

Bec was 5'6" with a thin body. She has a nice C size breasts but she didn't seem to overshow what she looked like. The more we talked, the more I fell for her.

That first conversation led to a few more dates where we would just sit and talk. Neither was in a rush and we both were honest and open with each other. She told me that her ex was her only sexual partner and it had all been really vanilla with mainly missionary in a bed.

I on the other hand had been with several partners and some of them had really stretched my comfort zone with different positions in all kinds of situations from outside in a park to actually having a girl ride me cowgirl in a dark corner of a frat house with others around at a party.

She was always asking questions about my past, how each position felt and what it was like. She really wanted to open up sexually but with a small son she was always very conservative, which was understandable.

It was almost a month before we made out on her couch one night and I went down on her. She tasted amazing and after a few minutes had an orgasm while gripping the back of my head. After that she thanked me and said that she wasn't ready to go all the way but wanted to return the favor. She had me stand up while she nervously unbuckled my pants and pulled out my cock. As she held it and it started to grow she looked up at me with a grin. Just then, she reached out and licked it from my balls to the tip. The feeling was amazing. Just when I thought it couldn't get any better she grabbed and and started to suck the tip into her mouth. She finally closed her eyes and started to do a long slow suck on me.

The more she did the better it felt. After a few minutes I ended up reaching down and grabbing the back of her hear and slowly fucked her mouth. She instantly started to moan as I did. The closer I got, the faster I stroked in and out of her mouth. She latched down with her mouth and was constantly moaning. I finally let her know that I was going to cum and she just kept going. Finally when I came she swallowed as quickly as she could.

Once I had finished and started to soften, my cock slipped out of her mouth and I fell back on her couch out of breath. She just slid up beside me, still in her bra and shirt, with her panties and skirt on the ground while my limp dick fell to the side and my pants were around my ankles. It was heaven while we cuddled.

As we were laying there she let me know that was the first time she had an orgasm from someone going down on her. Her ex would never do that and either wanted to just climb on top of her to get himself off or have her quickly give him a blowjob. Her sexual experience was limited but she enjoyed testing her boundaries and trying new things. She really enjoyed me fucking her face because she had never experienced that either. She generally would be asked to lick him until it was wet and jack him off while he sat back with his eyes closed. That's when she told me she was hesitate to go further with me because I was longer than her ex. That shocked me considering I wasn't that big or thick. So no wonder she almost never had an orgasm unless she did it herself.

That night was a turning point for us. After that I went out quite a bit with her and her son. we started hanging out and a few weeks later once she put him to bed she asked me to spend the night. I couldn't agree fast enough.

The first time that we had sex it was missionary and very slow. We took our time and enjoyed each others bodies. I found out that she really loved her nipples being sucked and really got off on looking face to face while we fucked.

The next morning wasn't as awkward as I thought it would be around her son, so it took the edge off of everything. I was the first one up so as I started to make coffee he came in the room and I made him some cereal. We were talking about the cartoon that was on when she came out of the bedroom. She was in a big T-shirt and panties and looked more beautiful than I had ever imagined. She just grinned at me and poured a cup of coffee.

After that first night, I started staying over three or four times a week. She was always up to try something new. Her favorite new position was doggy style. She really liked it when I would pull her hair while I hammered into her. She ended up screaming an orgasm into a pillow so she didn't wake up the whole apartment complex.

After about six months we had started a familiar routine. We would have amazing sex, using different positions, toys I had bought, blindfolds and anything else we could think of. She was really getting into her own and was even dressing sexier. She was generally wear tight fitting jeans but started wearing tops that were cut lower and lower showing more and more cleavage. She loved to see the lust in my eyes every time I saw her.

Then the day happened that changed it all. She came home after work and I had been making dinner for us. She said that she got pulled over for speeding, but got out of it with a sort of warning. I asked her what that meant as she poured a glass of wine and drank a few sips.

She said that the officer was a really good looking guy who really took a liking to her. They talked while he ran her license. He then said that he would love to take her to dinner and see what he could do to make the ticket go away. So she gave him her phone number and then he introduced himself as Ben.

I didn't know what to say but that night we had mind blowing sex. As we were sitting there in the afterglow I brought up that Ben had her number and what would she do if he called. She really never answered me straight forward. So I asked her if she thought he was sexy and I slid between her legs. Since we always used a condom, there was no remnant of our first encounter so I just started to lick her. I knew i was on the right track as she started to moan. I started asking questions as I kept licking and using my fingers to get her excited.

"Did you like the attention and the way he looked at you?"

"yes......"

"Did you think he was attractive?"

"yes....."

"Did you imagine what it would be like to kiss him?"

"Maybe...."

"Be honest, did you imagine screwing him?" as I slid a finger in t was wetter than usual.

"Okay, yes, I thought about it and got wet thinking about it."

"Is that something you would want to do?" This really got her going as I put two fingers inside her.

"I don't know........"

I stopped licking and put a third finger inside her as I looked up at her. "Be honest. Do you want to fuck him?"

"YES! YES! YES!" she screamed as she had an orgasm.

I didn't take long for her to come down from her high and then flip me over and ride me. As she rode me she kept having smalll orgasms and she chanted "Fuck me Ben! Fuck me Ben!"

When I was close I pulled out and stroked myself a few times before I came on her stomach and breasts. I then collapsed beside her.

As she got up and went to the bathroom my head was spinning. I didn't know what this meant or what just happened but I knew that it made me hard and it was hot.

When she came back and snuggled up to me it took a few minutes before she started to speak. "I'm sorry, I don't know what came over me. I shouldn't have said any of that."

"Was it the truth, do you want to experience a different guy?" I looked straight into her eyes and tried to show her I was interested and not hurt.

"I don't know, kinda. I just felt like I missed alot and I'm so behind in my sexual experiences. Time with you has been amazing but I just hate that I missed so much married to my ex.?

I gave her a moment and then said, "I think you should call him."

"What?!?!?" she said jumping up to look me in the eye.

"I'm serious, you should call him and at least go to lunch. If things look like they might go good, then we can take the next step. I love you but I don't want you to ever have any regrets if this is going to work."

She was quiet for a while and then let out a "Okay.......thank you so much."

Things went back to normal and then two days later I went to her house for dinner. While we were cleaning up afterwards, she said "so Ben called me today." and let it just hang in the air waiting on my response.

"Oh really, how did that go?"

Her face lit up with a smile and she looked at me with enthusiasm. "He was so nice. we talked for about an hour. He wanted to go to lunch tomorrow but I told him I wasn't sure if I could get a baby sitter." She kept looking at me waiting on a response.

I looked her straight in the eye and said "call him and tell him you have a babysitter. I'll watch your son while you go to lunch with him."

"Really?" she said and when I nodded she lept into my arms and kissed me hard. She then led me into the bedroom and spent the next hour giving me an amazing blowjob.

While we laid in bed that night she slept soundly but I just kept tossing and turning thinking about lunch. What it would be like? Where was this heading? What did he want out of this situation?

I mean it was no secret I loved Bec and her son but I just wasn't ready to commit and get married. What if he was? But the more I thought, the harder I my cock got. I slowly got up, went to the bathroom, just shut the door and slowly stroked my cock while I imagined them having lunch, touching hands, starting the kiss, and then other things. My mind started imagining the faceless man fucking Bec and her letting go and having rolling orgasms. Then all of the sudden I came all over the mirror. I quickly cleaned it up, flushed the evidence and went back to bed and spooned Bec until I fell asleep.

The next morning was a blur with her asking me a few times if I was still good to babysit today. I told her no problem I had arranged to work remotely so I was good to be here all day. She got a huge grin on her face and then went back to the bedroom to get ready. When she came out she had had a shower and was in a short black skirt with a white top. If you looked hard enough you could see a black bra underneath and lots of cleavage. I got hard just seeing her.

One last time she came to me and said, "Are you sure you are good babysitting?" looking me in the eyes.

"Yes, I am positive. Go have fun."

She squealed, kissed me on the cheek, kissed her son on the head and went out the door.

I didn't get much work done that morning. She had left at 10:30 and supposed to meet him for lunch at 11. When I looked at the clock it was 11:30. That means that they had already met. What were they doing? Did he like how she was dressed? Did she think he was hot? What were they talking about?

It was all too much. I looked over and her son was still enjoying his cartoons. I wanted to go rub one out but knew that wasn't the responsible thing to do. Instead I just tried to focus on work as the minutes went by.

Finally I looked at the clock and it was 2:05 pm. Where they still there? What could they still be doing? My answer came in the form on a text.

My phone buzzed and I immediately grabbed it.

HEY, SORRY I HAVEN'T RESPONDED. WE'VE BEEN HAVING A GREAT TIME. I'M LEAVING NOW AND SHOULD BE HOME IN 30 MINUTES.

I was a flood of emotions. Relief, jealousy because it had went well, anger because the text was so short. But the main thing was I was extremely hard.

When she came in a little later she still looked as amazing as she did before but her hair was a little messed up, as was her lipstick.

She saw that her son was asleep in his room and just took my hand and led me to the bedroom. I instantly thought we would have sex but she sat down on the bed and asked me to sit with her.

I sat down suddenly not knowing where to look.

"Thank you for letting me do that. It was amazing."

"I'm glad you enjoyed it." I said not knowing what else to say.

"He is really nice and charming. I think you would like him."

I wasn't sure what to say so I finally stumbled out. "I was getting worried, lunch went a little long."

"Well I have a confession to make. We ended up eating and having a great time. Then he suggested a coffee shop and drove us there. After coffee and more conversation we got back in his car. That's when he kissed me. It was electric and the hottest thing I've ever done, knowing you were here waiting on me."

There was a long pause so I finally chose to break the silence, not really wanting the answer.

"Is kissing all that happened?"

She blushed and then finally spoke. "No, after we kissed for a while and he felt me up, I ended up rubbing his cock through his pants. It felt huge, like bigger than I've ever imagined one to be. Please don't be mad and I know this is going fast, but I had to see it. So he ended up sliding his seat back and I took his cock out and sucked it."

"Wait, you gave him a blowjob in a car, right after you met him?" My head was spinning but my cock was straining against my pants threatening to bust out.

"Yes I did, I don't know how it happened but I just had to see it and taste it. It was really thick and long. It didn't take long, he kept telling me how great a cocksucker I was and I just got more turned on. Then finally he exploded in my mouth and I just swallowed it."

It was at the moment that I realized she had just come in from meeting him and kissed me.......with cum and cock still on her breath before this conversation. I was guy punched but also aroused.

"Thank you so much for letting me explore my wild side, and it looks like you need some relief as well." as she stroked my cock under my jeans.

Without another word she pulled me to my feet, got on her knees and started to fish my cock out of my pants. As she blew me I was in heaven because it was amazing but I was also imagining everything she had just told me.

She pulled her mouth off my cock and was just stroking it as she got up on her feet and was talking into my ear.

"He wanted to take me to dinner tonight. Would that be okay? I called my mom and she's going to watch my son."

I was trying to process what she had said but also what I was feeling. Then she leaned in close and said.

"I just had one more favor. Since this was your idea and I don't feed safe going to his house, would you rent me and Ben and hotel room while we are at dinner?"

I came all over the floor and relaxed back onto the bed fully spent.

She crawled up next to me, my pants still around my ankles and said "Is that a yes?" with a grin on her face.

I'm not sure why I did it but I just nodded yes.

She squelled with excitement and kissed me on the cheek. "Thank you so much! I love you! I have to go text Ben and then pick out something to wear. Could you clean up your mess when you recover sweety?"

So there I was laying on the bed, my pants around my ankles, my limp cock still pumping a few drops of cum and my cum on the floor for me to clean up. In the other room, my girlfriend was making a date and getting in the shower to freshen up for her evening and night in a hotel with another man.

The only question going through my mind.........."which hotel does she want to go to?"

To be continued.