This is part of a multipart story. For context you may want to start at part 1. Otherwise some of the themes will seem weird. Thanks for reading, hope you enjoy, please remember to vote and comment.
Met friend and past lover Lisa at a hotel for a Christmas catch up. I’d helped her out financially during a long unemployment period for her. It had coincided with a family member needing care and her time.
Lisa wanted to “Thank me personally for helping her out”.
It was Lisa that suggested the hotel. She had also been very clear she wanted extreme rough roleplay, extra everything she had said. I was hoping she might let me bring my current girlfriend. Lisa said she’d think about it, then ruled it out a day before start time. It was just as well as I’d talked about the meetup with my girlfriend. She was very understanding about my friendship with Lisa. my girlfriend did not want to see Lisa. The drunken behaviour upset her. She told me to go and have fun, especially do all the dirty things with Lisa I used to enjoy.
My girlfriend and I had an open honest relationship. We used to tell each other about wild times in our past while fucking. Lisa often starred in some of my stories.
I brought lots of champagne and a small bag. First mistake, I’d forgotten to never exceed 3 or 4 bottles with Lisa. Lisa met me in the Hotel lobby. She had a concierge take my bags upstairs.
We had the first bottle at the cafe downstairs on the street side. Second mistake – no food with the alcohol drinks. Once the first bottle was gone Lisa said “I’m going upstairs to change, give me ten minutes then come upstairs for your massage. Remember to be sexually assertive”
I said “can you be clearer about that” Lisa gave me a lewd smile and said “force me to do anything you want, I’m going to fight you, so it won’t be easy. I want it really rough! Not your usual baby girly stuff. This is on my terms not yours.”
I still wasn’t clear what exactly ’it’ was but Lisa had given me some fabulous massages in the past. I was in and hoped for a special night.
I sat out 8 of the 10 minutes downstairs, then went to the service counter and asked them to put a bottle of champagne at the room door but not knock. I then went up to the room. A quick knock and Lisa answered the door opening it, but staying behind the door. I came in and as she shut the door she said “you are fucking late. Price is $200 now”
I replied “$200 is a lot of money. I need to know you are worth that much”
She was walking past me so I grabbed her throat and she turned away from me. My other hand touched her inner thighs. They were bare inner thighs, as she was wearing a tiny short skirt. I pushed my hand in under her firm ass, feeling her thong and swollen wet pussy lips. I roughly shoved two fingers into her tight wet pussy, then firmly pushed my thick thumb and her G-string ribbon into her tight dry ass.
She screamed “fuck, stop that you bastard. Get out of here, massage is cancelled”.
I pushed the two fingers deeper in to her pussy and pulled the thumb out of her ass. I quickly pushed her face into the wall and pushed the two pussy wet fingers into her ass. They slipped in easily and she barely stopped herself pushing back onto them.
I said “you’re not wasting my time bitch. You agreed to this meet. You said tonight would be hot, now you’re going to give me hot.“
I pumped her tight ass with her pussy juice lubricant and relaxed my hand on her throat. She Immediately bit my wrist and twisted out of my grip. She stepped towards the bed and said as she twirled for me “does this look like a time waste?”
She was wearing thigh high stiletto black slut boots, a red purple dress that showed her ass curves below and a busty top showing half her tits in a push out bra. She asked “do you like my slut outfit? Will it make your cock hard? Watch out when I bend over.”
With that she stepped to the window sill, putting both hands on it. Lisa placed her legs apart, pushed her ass out to me and her short skirt rode up showing her pink tiny ass hole directly to me.
She said in a commanding voice “you hurt my ass hole with your rough fingers, kiss it better with your lips and tongue or you have no chance of getting your big hurting cock up there.”
Lisa wriggled her sexy size six ass at me for emphasis.
I walked forward and got on my knees behind her and lifted her tiny red/purple slut dress above her ass then pulled her G-string down over her black boots. With her help I removed her G-string. I held her dress up and started tonguing her anus. She was right into it, pushing back and loving my warm tongue in her private places. Sometimes she would tilt her hips and push back. My tongue would go all along her pussy slit and push against her clit.
After 5 minutes of this Lisa was panting. Lisa stood up and said “This is not the plan. You are supposed to be assertive and take what you want. Not some polite little ass licker tonguing my ass for my favour. You can get out. I’ll find a real man to make me fuck him.”
Lisa pushed past me. I felt my cock was rock hard. I stood and grabbed her in one movement then pushed her face down in the bed. Again, I used one hand on her throat, the other aligned my cock onto her saliva coated anus. Her well licked hole stretched to accommodate my thick hard cock head.
I felt my cock head penetrate her ass. She was so tight. I used the full weight of my body to fully push my cock up her ass, until she had the full length deep in her ass. I grabbed a handful of her head hair and pressed her skull into the bed. I then commenced to pull my hard cock out of her ass, then forcefully push it back into her.
Lisa was gasping and shaking, she said “Oh the little ass licker has found some balls. Use them you fucker, fuck my brains out. Don’t make me tell you again.”
I had brought a little bag of tricks along to push our boundaries during the night. After fucking her ass roughly for 15 to 20 minutes, my cock was getting sore and I needed a break. I knew she would complain bitterly if I stopped and did nothing. I grabbed the little bag and got a small 10mm thick rope out. Then roughly grabbed her hands behind her back and did a truckies hitch on each wrist then wrapped the rope around each wrist and the joined bundle and did many knots to ensure they would stay put.
I then got a ball gag out of the bag and forced it into her mouth. She fought me as this was new and we had not agreed on it. Once the gag was in place, I got some soft sleeping mask eye covers out and put them on her head. I knew she was a little scared as this was all new. In her scared state she was actually enjoying the huge hard cock up her ass and was fucking onto and out of my thick cock. It was feeling really good. Her ass was self-lubricating and her cunt was dripping juice.
I got another rope out of the bag. I had to pull out of her and tied her feet together and to the rail of the hotel bed.
Once that was done, I was immediately back in her sweet ass. I was enjoying fucking her and feeling her pulse and shake from the force of the anal fuck. I pulled out of her sweet tight pulsing ass and smacked her ass really hard with my hand. I said “Well slut you better start being fucking respectful now. You’re all tied up, blindfolded and gagged. You can’t go anywhere or do anything, except be a hole for my cock, until I’m ready for you to stop.
She started struggling and trying to shout. She was barely audible. I shoved my big cock into her ass again making her pulse. I got up and smacked her ass again and said “I’m bored with your stinking little ass. Think I’ll take some sweet wet pussy now.” I grabbed fat vibe from her bag and shoved it in her ass and turned it on to a high buzz rate. I took a few pics of our handiwork then set an alarm on my phone that sounded just like a phone call on Lisa’s phone to occur in 5 minutes.
I then got up and washed my cock while talking to her. I said “Think I’ll have to ramp it up as you are always calling me names and saying I’m not dominant enough with you. Time for me to push way past your barriers. Get to the places that stretch what you want.”
With a clean cock I pushed hard into her tight little wet pussy. I could clearly feel the buzzing vibe still in her ass. This was not new, we had done this plenty of times.
I got up and walked to the phone, lifted the handle and typed the 3 digit room service number so she could hear it, then silently pushed the phone rest down to disconnect the call. I said “Hello this is room xxx, we need some extra towels, and a bottle of the best champagne. Yes book it to the room. Thank you, ten minutes excellent. Goodbye”
I went back to her and roughly pulled the anal vibrator in and out a few times. Then shoved it deep back in her ass and fucked her tight wet pussy with my hand to make her squirt. She did a lovely big squirt and I raised my hand to taste it and the scent of her clean pussy made my cock throb.
I fucked her tight pussy again then squeezed her nipples hard to make her cum. She didn’t cum. The bitch was denying me the enjoyment of watching her cum.
Suddenly there was a loud sound of a phone ringing. It was the alarm I set. I acted like I was answering the phone but just turned off the alarm. I said “Oh Hi Sue, yes nice to hear from you. Yes Lisa and I are away for the weekend. Oh you knew. Wonder why she did that. No Sorry she is tied up right now and can’t talk. Yes she’s fine. I can get her to call you later. OK will do. I didn’t know you were in town. Yes I could come n have a drink with you down stairs. Well now really, can come right down. OK a couple of minutes. Yes it would be nice to see you without bossy Lisa running everything.”
I acted like I hung up the phone. I had a quick shower, then checked Lisa was ok. I said “I’m going downstairs to fuck Sue, sorry have a drink with Sue. Wonder why you had her as your backup plan. Might have a drink and fuck her.”
She was struggling a bit and growling into the gag.
I put a dressing gown on, and went outside the room. The passage was deserted. 1 minute later I knocked on the room door. I said loudly “Room Service”, waited 15 seconds then knocked again and called again “Room Service”.
I used my door key and opened the door. I said in a fake French accent “Room Service” and walked inside shutting the door. I put the champagne on the table, and said in the fake accent “Are you ok Madame.”
Lisa was totally silent and still. I dropped the dressing gown to the floor and got my rock hard cock in my hand. I got on the bed on top of Lisa and pulled the vibe out of her ass. She stayed silent and did not move. I pushed my hard cock half way into her ass and started fucking her. I never went fully deep. She did not move for about 5 minutes, then suddenly she started shaking and had a massive orgasm including squirting onto my balls. What a fucking slut, cumming because she thought she was being fucked by a random stranger doing room service.
I pulled her up on her knees into doggy and fucked her ass to the smaller depth until she came again. Her orgasm was very intense including hard squeezing her ass on my cock. She was amazingly orgasmic this night. I continued to fuck her hard and over 30 minutes she came maybe 10 times. That was easily a record for her cumming with me. It was about what she claimed she could do alone, or with her previous young lovers.
I then came in her ass, blasting a big heavy load into her tight little shoot.
I got up, put the dressing gown on and opened and closed the door. I stayed inside and listened. I could hear Lisa start to cry. That really surprised me. I’d seen pretty much every emotion from her but never heard or saw her cry.
After a couple of minutes, I loudly opened and closed the door. I walked into the bedroom saying “That Sue can really suck cock.”
Then I looked at her, cum leaking out of her ass and the vibe out on the bed.
I said “Oh you have spat your vibe out, why would you do that”
She had stifled the crying. I got on the bed and said “I’m still half hard after blowing in Sue’s mouth. She said you had organised it as a Christmas present for me. Thank you.”
Obviously, I had been in the room with Lisa, all the time. I had not seen or touched Sue. To my knowledge, Sue was still back east with her mother.
I slammed my hard again cock into Lisa’s tight ass. I loved the feel of my cum, as lube in her ass. I had no idea if she had fallen for the trick about the room service guy. I did not think she would fall for it really. The crying had confused me.
I fucked Lisa hard, full depth and after 10 minutes could not stop myself cumming in her ass.
I started untying her and took the gag out. I said “Were you worried while I was gone? Hey how did the champagne get inside.”
Lisa said nothing.
I said “That’s weird, there’s no way you could have let room service in. They must have come in. They had to walk past you naked on the bed, to put the champagne on the table. Hey the vibe was out of your ass. Wait a minute, your ass was lubed up with cum. Did you let the room service guy fuck your ass.”
Lisa said nothing. She could have said “It was you” or “Nothing happened” or “It was your fault”
Instead, she said nothing.
I got her a drink. Third mistake, still nothing to eat.
Lisa did not want to talk about being upset. Forth mistake, don’t let Lisa simmer when she is upset.
We started partying again. Music up. I was serving the drinks. When one bottle was empty, I just opened another. By about midnight we had drunk all the champagne in the room. Fifth mistake, don’t give Lisa lots to drink when she is already upset.
That night after that role play game, Lisa had been drinking really heavily. Initially we danced, ate a little and laughed. I did say she should slow down on the booze a little to prevent a train crash. She got argumentative around midnight. I tried my best to settle her but she stormed out of the hotel drunk around 1am. I looked for her on the street, and told the hotel security. I rang another mutual friend, who lived near Lisa. She said she would keep an eye out. She texted me around 3am that Lisa was home.
Lisa apologised a week later. I said I was a bit disappointed with her behaviour. By then it was Christmas, so I was busy being away with family for the Christmas break. I didn’t see Lisa for about 4 weeks. When we did catch up, I said I had been worried about her safety, after that the topic wasn’t discussed.
It was months before Lisa told me she had been fucked in the ass by a waiter around Christmas time. I knew it had to have been that night at the hotel. She confirmed it was after she had stormed out of the room.
I told her it was a role play game and it was me in the room that fucked her. She replied “The one in the room might have been you, I suspected it was you, but never knew for sure. The waiter down stairs, the one that fucked me in every hole in the car park after I left the room, that was clear enough not you.”
I said “Gee that happened fast, how did he find you. Why didn’t you just come back to the room. I just don’t think I said or did anything to deserve that treatment. If the role play was what upset you I’m really sorry. It was along the lines you had told me to do for role play.”
Lisa hung her head and said “I was really upset, he found me in the basement looking for my car. He was going to call the police. I told him to fuck me instead. He’s a guy, of course he fucked me.”
I said “Do you want me to follow up with the hotel, staff should not take advantage of guests. Does not matter if they are drunk. I know we are just friends and you can do what you want sexually, but I feel responsible that that staff member basically raped you.”
Lisa said “No just forget it. It was my fault. I was angry and wanted to get back at you because I was angry.”
I said “I’m still going to take it up with the hotel.”
Lisa said in a very angry voice “No leave it alone. Can’t you fucking understand, I loved it. I’m a worthless disgusting fucking slut. I loved him fucking my face and ass in public, in the bloody basement. I wanted it. I asked for it. I sucked his cock after he fucked my ass. If there’d been any more staff around, I would have fucked them too. I’m a fucking whore. I’m not worth your friendship.”
I said “Were you angry at me for the trick about the waiter in the room. I thought you would work it out and love the dirty scenario. You did go off big time.”
Lisa replied “I did love it. I still do love it. That’s why I got so angry. You reminded me of how much guilt I have, how disgusting I can be when I let the Lisa Monster out of the box. How the most disgusting horrible things I’ve done in my life, are the things I think about most when I fuck myself with the biggest toys I have.”
I said “I usually like the Lisa Monster.”
She replied “You have never really seen the real Lisa Monster. I am a whore.”
I said “We have done pretty much everything sexual together and most role play that there is. What else can there possibly be?”
Lisa said “The truth.”
I sat there looking into her eyes for a long minute. She put her head in her hands and started to cry. It was the first time Lisa had cried in front of me knowingly in the years we had been friends.
That discussion led to me talking Lisa into having grief counselling. She needed it for whatever trauma she had bottled up inside her. That lead to many changes in the friendship and many changes in Lisa’s risky lifestyle choices.