Watching Jessie at the Hotel

This is a continuation of the story Watching Jessie (glory hole).

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By the time I got Jessie dressed to leave the glory hole booth another cock appeared through the hole in the wall. Jessie wasn't about to leave it there. Jessie promised that she just wanted to practice her sucking skills. Jessie knelt down in front of the cock and began kissing and stroking it. As the cock began to grow Jessie stroked it more and licked it all over paying special attention to the head. When the cock was fully hard Jessie took it into her mouth. I watched as Jessie bobbed her head back and forth on the rather long cock. Jessie was making a slurping sound as she worked on the cock. Jessie stopping for a moment when she gagged but went right back to deep throating the cock.

I needed to get my cock in Jessie's pussy. Watching was amazing but I was ready for me to have my turn. I ran my hand up between Jessie's legs pushing them apart. I easily moved Jessie's thong aside and slipped two fingers into her sopping pussy. Jessie wiggled a little to try and get me to stop but she was focused more on the cock in her mouth then what I was doing. Even though I didn't have a condom I was going to try and slid my cock into Jessie's loose wet pussy. I had my cock in my hand as I knelt between Jessie's legs. I pushed my cock between Jessie's legs. I could feel the heat from Jessie's pussy on my cock. I slid my rock hard cock back and forth against Jessie's pussy. It felt amazing and even though I couldn't get my cock inside of Jessie's pussy the way she was positioned I was still about to explode. I stopped stroking my cock against Jessie's pussy not wanting to cum yet.

Jessie was still sucking voraciously on the cock from next door. I had pulled my cock out from between Jessie's legs to cool down some. I could hear the guy moaning through the wall as Jessie gobbled his cock. I repositioned myself and pushed my cock back between Jessie's legs. This time my cock was pointing upwards more. I felt the heat from Jessie's pussy on my cock once again. Then it happened, my bare cock entered Jessie's pussy. Jessie's pussy was hot and wet even though it was unusually loose I dared not move for fear of cumming inside of her. Jessie was swallowing hard as the guy shot his cum in the back of her throat. Jessie pushed back against me her pussy seemed to convulse on my cock. It was too much I pulled my cock out of Jessie's pussy shooting my cum as I did. Most of my cum was on Jessie's pussy but some was inside of her and some on the floor.

Jessie finished cleaning the guy's cock then wiped her mouth off with a paper towel. Jessie said let's go as she looked at me and my still hard cock. Jessie opened the door. I quickly tucked my cock away and tried to suggest to Jessie that she might want to wipe my cum off her pussy. Jessie paid no attention to what I was saying. Jessie walked proudly back out through the store.

Jessie's phone was going off again. Jessie stopped long enough to pull it out of her purse. Jessie commented that she didn't know who it was as she proceeded toward the door. Once outside Jessie checked her calls and messages. Jessie had missed two calls from the same number and had a voicemail and also a text from the same number this is Frank. Jessie listened to the voicemail as we walked back to her car. Jessie suggested that we get a hotel room for the night. I thought that we had already decided to do that. I inquired about her voicemail and Jessie said that it was Frank and he wanted to get together.

Jessie was unsure if she wanted to see Frank. Jessie reasoned that he was probably ugly and it would spoil her memory of how good his cock had felt. Jessie asked if I thought I could drive to the hotel. It was only 3 blocks away I said I think I can handle it. Jessie texted on her phone as I drove. Once at the hotel Jessie wanted me to go in and get the room. Jessie would pay me back but she couldn't bring herself to go to the desk reeking of sex. When I got back in the car Jessie was talking on the phone with Frank. I parked the car and got the bag we packed just in case out of the trunk. Jessie finally got off the phone and got out of the car.

As Jessie and I walked to the room she told me about Frank. Seems that Frank is married. Frank's wife was out of town with their two teenage girls. Frank had heard about the adult bookstore and that you could get a blowjob there for next to nothing. Frank's wife hadn't sucked on his cock in years and he missed it. I opened the door to our room. Jessie didn't say anything as we walked into the room. Once i shut the door, Jessie put arms around my neck and kissed me I could taste the cum she had swallowed as she ran her tongue into my mouth. Jessie whispered I want you to fuck me. That sounded good to me. I started to take Jessie's clothes off. Once I freed Jessie's breasts I started to suck and kiss them. Jessie whispered when you're done I want Frank to come over. Was I ready for Jessie to take it to this level. It had been teasing up until tonight. Even the glory hole was without contact with the other person just purely sex. How could I tell Jessie no. I was the reason Jessie had come out of her sheltered lifestyle. Besides I wasn't sure if I wanted Jessie to stop.

Jessie didn't seem to be asking me any way. Jessie dropped to her knees and pulled down my shorts. Jessie lifted my cock out of the way and started sucking on my balls. Jessie began stroking my cock with her hand as I started getting harder. Once my cock was fully hard Jessie moved her mouth from my balls to my cock. Jessie had sucked my cock before but nothing like she was doing now. Jessie had her hands clutching my ass pulling me to her and forcing my cock down her throat. Thoughts of fucking Jessie's pussy left my mind. All I could think about now is Jessie milking my cum from my balls and sucking it out of my cock. I could hear Jessie gagging occasionally as she took all of my cock into her mouth. I couldn't hold back anymore and I shot my cum down Jessie's throat. Jessie made a gurgling noise as she swallowed my cum. Jessie sucked and swallowed all of my cum before getting up. I collapsed on to the bed. Jessie went in the bathroom.

I heard the shower turn on. After a few minutes I turned on the TV and scrolled through the channels. Jessie finally came out of the bathroom wearing a see through nighty she had bought for my Birthday. I was admiring Jessie's large but still perky breasts through the thin fabric. Jessie pulled back the covers and sat on the edge of the bed. My hands were roaming over Jessie's body as we gently kissed each other. I wanted to take my shower and make out some more with Jessie. However Jessie kept pulling me back for another kiss. I was startled by a knock on the door. Jessie seeing my surprise said that'll be Frank, do you want to let him in.

So this was it, Jessie had invited Frank to our room. Jessie wanted me to let him in there by consenting, I suppose. I got up and went slowly to the door as Frank knocked again louder this time. I peeked through the door. A rather large older looking black guy was there by himself. I opened the door. Frank stepped inside and grabbed my hand shaking it and thanking me for letting him come over. Frank made a rather imposing figure at over six feet tall and broad. Frank looked to be in his forties and appeared to have a bit of a belly. As quickly as Frank had grabbed my hand he let it go. Frank seeing Jessie standing by the bed in her see through nighty left me by the door.

Frank was telling Jessie how beautiful she was as I shut the door. Frank continued praising Jessie and thanking her for inviting him. Frank couldn't believe that Jessie had invited him. Frank had Jessie turn around so he could admire her from behind as well. Frank moved in close behind Jessie and put his arms around her. Jessie leaned back against Frank. Frank moved his hands up and began fondling and caressing Jessie's breasts. I was watching Jessie and Jessie kept looking at me. Frank leaned down and started kissing Jessie on the neck. Jessie titled her head back and closed her eyes.

I took a seat in the chair to watch the show. Jessie opened her eyes to peek at me then shut them again. Frank moved his right hand from Jessie's breast and slid it down across her stomach. Frank's hand moved down and he pushed his fingers between Jessie's legs. Jessie opened her eyes for a moment to look at me. I was still sitting watching. Jessie closed her eyes again and tilted her head back further. Jessie's lips parting as she started to moan softly. Frank was now rubbing his big hand against Jessie's pelvis. Jessie reached her hand behind her to feel Frank's cock through his clothes. I saw Jessie peek at me again as she felt of Frank's cock. Frank leaned down and put his lips on Jessie's mouth kissing her gently. Jessie rubbed Frank's cock and kissed him back. Frank pulled Jessie's nighty up so his hand was on her bare pelvis. Frank pushed his finger into Jessie's pussy. I could see Frank's finger glistening with Jessie's pussy juice. Jessie had stopped rubbing Frank's cock which was straining against his pants and pushing against Jessie's ass. Jessie broke the kiss gasping from pleasure. Frank continued kissing Jessie's neck and fingering her pussy until she came.

Jessie after cumming on Frank's finger turned around to face him. Jessie pressed herself against Frank and kissed him hard on the mouth. Frank's reached down and pushed Jessie's nighty up and grabbed her ass with both hands. Jessie had her arms around Frank's neck. Frank and Jessie continued kissing Frank's erect cock sandwiched between them as Frank's big hands groped Jessie's ass. Then Frank picked Jessie up. Jessie wrapped her legs around Frank. Frank was rubbing Jessie's pussy and ass with his fingers as well as his big cock which was straining against his clothes pressing against Jessie's pussy. Jessie broke the kiss moaning and asked Frank if he was ready for a blow job. Frank said not yet. Frank sat Jessie on the bed and pulled her nighty off over her head. Jessie's nipples were hard already. Frank had Jessie move further onto the bed as he climbed on the bed, kneeling between Jessie's legs.

Frank put his hands on Jessie's breasts and massaged them. Frank then leaned forward and kissed and sucked on Jessie's breasts for several minutes. Jessie after a short time pulled Frank's shirt up. Frank took a break from Jessie's breasts just long enough to finish pulling his shirt off. Jessie's hands look tiny against Frank's large black body as she ran her hand up and down his side. Jessie was moaning either from Frank's attention to her breasts or his large cock rubbing and pressing against her pussy. Jessie slipped her hands between her and Frank and unfastened his pants. Frank raised his hips up still sucking and kissing on Jessie's breasts. Jessie worked Frank's pants down until his huge black cock sprang free. Jessie ran her hands over Frank's cock.

I was shaking from the sight as Frank removed his pants lowered his hips back down his bare black cock disappearing between Jessie's legs. I hadn't expected Jessie to let Frank put his cock in bare. I was scared, nervous and excited all mixed together. Jessie had her arms around Frank moaning loudly as he continued sucking and massaging her breasts. Trembling I moved around to see better between Jessie's legs. All I could see through was Frank's big black balls resting on the bed. It looked like Frank was too far down for his cock to be inside of Jessie. Frank raised up off of Jessie enough for me to see that the tip of his cock was pressed between the lips of Jessie's pussy. It was a relief but I thought that Frank was going to push his cock into Jessie's pussy now. Frank then asked me if I was okay I guess because I was standing so close shaking. I shook my head. I finally managed to ask Frank if he needed a condom. Frank didn't answer for a moment apparently thinking about how to respond. Frank finally said that it was up to Jessie.

Frank raised up off of Jessie kneeling between her legs. Frank stroked Jessie's pussy with his hands and rubbed his cock all over her pussy. I got the package of condoms out of my bag and put them on the bed. Frank moved down and he began kissing Jessie's belly. Frank worked his way down. Jessie gripped the sheets as Frank's tongue flicked across her clitoris. Frank continued licking, kissing and sucking on Jessie's pussy. Frank reached up and caressed Jessie's breasts while he feasted on her pussy. Jessie was moaning like crazy and was letting out a bunch of ohhhh oh ohhhh fffu ohhhh ffuck ohhh ohh fu ohh fuck yeah. Hearing Jessie had my cock getting hard again and I'm sure it was having the same effect on Frank.

Jessie finally unable to take anymore said I need you inside me now. Frank raised his face up from Jessie's pussy. Frank was kneeling between Jessie's legs and I handed him a condom. I could hardly believe the size of Frank's cock or balls. Frank's cock must have been close to a foot long and thick as a soda bottle.

Frank nodded to me in acknowledgment as he took the condom. Frank worked the condom on to his cock as far as it would go. Frank eased forward and rubbed his cock against Jessie's pussy. Jessie was moaning as Frank rubbed his cock between the lips of Jessie's pussy spreading them apart. Jessie's juice was coating Frank's condom covered cock. Frank pushed his cock into Jessie's pussy making Jessie gasp. Frank slowly pushed his cock farther and farther with each stroke. In a matter of minutes Frank put Jessie's legs on his shoulders. Frank humped his cock rapidly into Jessie's pussy his big balls slapping against Jessie's ass with every stroke. I listened to the smacking sounds and the sloppy suctioning sound as Frank pounded into Jessie. Jessie cried out in pleasure over and over as Frank fucked her hard for a long time. Frank's back was wet from sweat when he finally announced that he was going to cum. Frank grunted as he rammed deep into Jessie's pussy. Jessie yelled out oh fuck as Frank ejaculated.

Frank leaned down and kissed Jessie tenderly on the mouth for several minutes. I realized that I had a big wet spot on my shorts though I hadn't even touched myself. Jessie told Frank that was amazing. Frank said I hope you enjoyed it as much as I did. Jessie insisted that she had enjoyed it more than Frank did. Frank finally pulled his cock out and rolled off of Jessie. Jessie said damn, that could get addicting. Frank smiled then said I hope so. Frank played with Jessie's nipples a little then gave her a kiss as he got up to go in the bathroom.

Jessie was excited as she said to me oh my God that was amazing...can I keep him. I smiled back at Jessie and said I guess you liked it. Jessie asked is that okay? Yeah I replied. I sat on the bed next to Jessie and gave her a kiss while I fondled her breast. Then I had to see Jessie's pussy. I moved down between Jessie's legs and checked her out. Jessie's pussy looked very different it was opened up so I could see inside and very red in color the lips were puffy. Frank came back out of the bathroom while I was checking out Jessie's pussy.

Frank walked back to the bed and picked his pants up off the floor. Jessie asked you aren't leaving? No, just picking my clothes up...why said Frank. Jessie said I don't want you to leave yet. Frank laughed and said I can't leave you promised me a blow job. Jessie laughed and said oh really that the only reason you're staying. Frank said hec no you are sexy as hell. Jessie smiled at the compliment. Jessie then asked when do you have to leave. Frank asked are you trying to get rid of me? No Jessie said. Frank said he didn't have to be home until tomorrow afternoon. Jessie then getting excited said you can spend the night. Frank said sure.

I went in the bathroom to shower, since it seemed that Frank was going to spend the night. Jessie and Frank talked while I was in the shower. I found out later what about. Frank and Jessie talked about where Jessie and I worked. What Frank did for work. Frank's relationship with his wife. Our relationship. Frank's wife was very suspicious of him not because he cheated on her but because he could. Frank was the CEO of the company his wife's father had started. Frank's wife Terry was always checking out who Frank hired at the company. If it was a female employee Terry wanted to see them and know what they were hired for. Frank told Jessie that he could have a well paid position for me if we were interested.

When I came out of the bathroom Jessie and Frank were laying on the bed together still talking. Jessie seeing me said I looked refreshed. Frank started running his hands over Jessie's body. Jessie in turn started running her hands over Frank's body. Frank kissed Jessie tenderly. Maybe it was just me but Frank seemed to want to make out with Jessie more when he was sure that I was watching. It didn't matter Frank was a married man and Jessie was going home with me tomorrow and would at best rarely see him again. I got in the other bed but sitting up to see what Frank and Jessie did.

Frank whispered something to Jessie. Jessie nodded. Frank turned crossways the bed his feet towards me. I soon realized what Frank must have whispered. Jessie moved and put her head on Frank's round stomach and massaged his balls in her hands. Jessie soon moved her mouth to Frank's balls. Jessie had to suck on Frank's big balls one at a time. Jessie spent a long time sucking on Frank's balls eventually Jessie began to slowly stroke Frank's cock as it began to grow. All I could think of is that it looked like Jessie was making love to Frank's cock and balls. Jessie finally moved her mouth to Frank's cock. Jessie licked Frank's cock lovingly and caressed his balls. Jessie then knelt on the bed her ass to me as she sucked Frank's cock her hands stroking his cock and caressing his balls.

I could plainly see Jessie's pussy still opened from Frank's huge black cock. Thinking about how Frank had just Fucked Jessie had my cock hard. I quietly got off the bed and carefully got the condoms off the other bed as I walked to the bathroom. In the bathroom I opened a condom and rolled it onto my cock. I returned to my bed. Jessie was still kneeling leaning over sucking Frank's cock. I stood behind Jessie and lined my cock up with her pussy. With one stroke I buried my cock into Jessie's stretched pussy. Jessie let out a little ooh of surprise. I grasped Jessie's hips and pumped into her for only two or three minutes before I came. Jessie never stopped sucking Frank's cock except to give her jaw a break. Jessie sucked on Frank's cock for between a half an hour and an hour before she finally gave up unable to make him cum.

Frank assured Jessie that it was fine. Frank excused himself to take a shower. Jessie got into bed with me. Jessie told me what her and Frank had talked about. Jessie wanted to know if I was interested in the job possibility. Of course I was interested but I would have to know what it was and how much it paid. Jessie asked if I was willing to move. Yeah if the right opportunity is there. Jessie said then let's ask him about it. I agreed.

Frank returned from the bathroom wearing a towel. Frank sat down on the other bed and Jessie instantly joined him. Jessie said I was telling him what you said about maybe having a job. Frank looked at me waiting for me to say something. I didn't know how to start. Finally I just asked do you really have a job if so what would I be doing and how well would it pay. Frank said it's more of a concept position but if everything worked out could be a six figure salary. Wow I thought that's almost four times what I make I wouldn't have to kill anyone I asked. Frank assured me that it was nothing illegal I'd be his executive assistant. I said it sounds good to me. Frank said Jessie probably wouldn't be able to work. This sounded a little unusual I looked at Jessie to see what her reaction was. Jessie said I think that I could do that. Frank went on about what he expected. It soon became clear that Frank wanted to be able to see Jessie on a regular basis and that I would be a decoy for Terry. Frank though added that I would be groomed to take his place one day. So there was another carrot. I would have to share Jessie with Frank though. I couldn't do that. Jessie said I don't mind being with you both. I said I need to think about it. Frank said that's understandable. Jessie then said to Frank can you give us a minute. Frank nodded and went into the bathroom.