I’ve posted about Jay before, he was one of my fwb when I was in my mid twenties, and how I fell for him despite having a loving boyfriend and even worse despite him constantly treating me like shit and putting me down.

On this occasion he’d asked me if I was going to be free one Friday night. I told him I would be for him. He replied great and asked me to send him some photos of me in certain lingerie and dressing up outfits I had. I was really excited he never seemed that bothered to see me it was normally me doing all the chasing.

I got home from work that day and asked my boyfriend to take all these photos of me and sent them to Jay to see which one he liked. He picked out a slutty tartan outfit (shirt tartan skirt, small white see through top and a tartan tie) which he wanted me to arrive me and told me to make sure I had my make up and hair done nice (a constant complaint of his was that I never made an effort when I always did) and then he told me to bring some blue lingerie that I had that I could wear later.

Friday came and all I could think about at work was how excited I was to go to Jays that night. After work I went home, had a shower, put on my makeup and made sure my hair was exactly how he liked it. Then I put on the outfit like I was told so I could arrive in it. I put a long coat on over it while I left my house but he’d told me he wanted me to park across the road from his house and watch me walk over the road and up his driveway dressed like that so I made sure I took the coat off while I was driving.

I got to his house and I had to park across the road and about five doors down so I had a bit of a walk dressed like I was! I rang him and said “are you going to look out the window and watch me walk?” He said yes and I had to walk slow I couldn’t run or he wouldn’t let me in. Ruined my plan to leg it towards his house lol. I got out the car and had to wait about 20 seconds to cross the road as it’s a busy road and had a couple of cars beep at me. Then when I finally crossed there was some chavvy lads sitting in someone’s garden smoking weed who made some comments so I just smiled and said “thanks”. Two other cars drove past and beeped at me too and the whole time I could see Jay looking out of his window laughing lol.

I got to his house and for once he was kind and let me straight in. As soon as I was in I started kissing him and trying to undo his trousers but he stopped me and said “not yet” and told me to go in to the living room. I walked in and there was some guy sat there who I didn’t recognise and I just said “oh hello” and then Jay said “here you go James, happy 21st, I told you I got you a nice present” and i was looking around for a present before I realised he meant me! This wouldn’t be the first, or the last, time Jay had shared me with his friends but it was the first time he’d done it without asking me. I’m ashamed to say I was that much under his spell and didn’t want to disappoint him or make him look stupid that I didn’t even argue. James was overweight and not at all good looking but then to be honest neither was Jay and I just wanted to impress him so I said “can I get you boys a drink?” And went to the kitchen. I got them both a beer and grabbed the bottle of wine I’d brought with me.

I walked back in to the living room and I sat next to James and gave him a beer (while I drunk some wine straight from the bottle) and then gave Jay his and he said “right I’m going to go upstairs, you two have fun”. As soon as he left the room James started kissing me and I thought “it’s his 21st let him enjoy it” plus I had a thought in the back of my mind that it would make Jay happy if I made James happy.

I climbed on his knee and started kissing him back while I dry humped him through his trousers. I could feel him getting harder straight away and then I leant forward and put my tits in his face while I drank some more wine straight from the bottle. He pulled my top open and started sucking my tits and I said “do you want sex or a blowjob?” I just wanted to get this done with so I could get upstairs to Jay. To James credit he said “whatever you want but I don’t have a condom” I told him I’ve got some in my bag so it’s his choice.

He chose sex so I went and got my bag and when I came back his dick was out, I put the condom on it for him and got back on top of him and slipped him in. My plan was to ride him quickly and make him cum quick and it worked perfectly. I rode him as fast as I could and I pulled his head in to my tits and probably 30 seconds later he was telling me to stop and he was done.

I climbed off him, grabbed my bottle of wine, drank some and went upstairs to Jay. He was in bed on the phone to a girl called Sam (I was so jealous of her he always said how she was better than me and better looking). I sat on his bed drinking wine while I waited for him to finish. He seemed in no rush and then just pulled his trousers down and got his dick out. I went to climb on him but he pushed me away and made the blowjob sign with his mouth so being the idiot I am I did just that and gave him a blowjob while he was on the phone to her. Like James downstairs he didn’t last long and he was still on the phone when he came. Once he was done I went back downstairs and sat with James.

I was feeling a bit drunk by now and had nearly finished my wine. Me and James sat there just watching tv and from what I remember he was actually quite a nice guy we were having a laugh together and he offered to get some food when I said I was hungry. Maybe it’s just because I was a bit drunk but the night seemed to get a bit better from there. Jay came down and we were all just laughing and drinking all night. Jay told me to get changed in to the other outfit I’d brought to show James so I did and about ten minutes later our food arrived that we had orders and they were both daring me to answer the door. I kept saying no but then thought fuck it why not lol. I opened the door in some see through lingerie with stockings and suspenders and I could hear them two laughing in the living room.

It got to about 2am and Jay said “what did you think to her blowjob skills then?” And James said “she didn’t give me one” I knew what was coming and said “come on James let’s give you a birthday blowjob” grabbed his hand and took him upstairs. We went in the spare room and I gave him head while he sat on the bed and then after he was done I ended up sleeping in his bed not Jays as Jay said he was going out, god knows where probably to see Sam. I didn’t do anything else with James apart from kissing and groping throughout the night, I did wank him for a bit but he couldn’t stay hard.

In the morning I thought “shit I’ve got to walk to my car dressed like that again” luckily Jay was still out so I asked James to go to my car and get my coat for me, I know Jay would never allow that. He did bless him so I put that on to cover myself up, gave James a big kiss and let him have my number and left.

I had no intention of doing anything with him again but he was good to talk to and we did text on and off for years until he met someone.

Jay messaged me the next morning and said I’d done a good job and James was happy which made me feel good knowing I’d made Jay proud (it makes me feel sick writing that now but I have to be honest).

When I got home I lied to my husband and told him I knew about James being there but I didn’t tell my husband to keep it a surprise. I felt terrible lying but I did end up confessing everything a few months later when I told my husband I had feelings for Jay and had to stop seeing him.