This is a 100% true story that recently happened where my GF and I decide to explore my first threesome as she meets my roommate for the first time. She and I have been together for almost four years but live in separate towns and we chat and video chat almost daily.
In the last 6 months I had started a job in a new town and decided to have a roommate since neither he or I would be there all the time. When we moved in together we joked that what happens at the apartment stays at the apartment. At first was just a joke but as things played out, it became real.
He had heard me chatting with someone one evening while I was in my room so I shared details about her with him, she was a high level executive, beautiful, sexy and in incredible shape. We found that we made each other better personally and professionally. I will briefly describe her. She is in mid/late 40s, 5'10", blonde of Scandinavian descent with blue eyes. Thin and toned body as she works out with a flat stomach, beautiful ass, and the best skills in bed I have ever been with orally and more.
Our sex life was incredible when together and when we chatted online we discussed sex intimately. Sexual fantasies came up every now and then and she shared she had done a 3sum when much younger. I had never done but wanted a 3 very much so we talked about it quite a bit but the odds of it happening were small with how much we both had at stake. Meaning we couldn't do with a stranger and didn't want to do with someone we knew as we didn't want to hurt our relationship.
This is where the new roommate comes into play. She and I openly chatted after he knew about her and I shared some pictures of her with him (with her approval). After seeing he offered to share back with her if she wanted which she did. He was 6'1" and in great shape as well as he worked out. The pictures showed his cock was above average in length but maybe not as thick as mine, she thought it was "very nice" and would love to see in person.
She and I wondered if he could be a possible 3rd. She asked if I trusted him, what I knew about him, etc. I felt comfortable with but this was new ground for me and I was nervous about doing and how would I feel during and after. I hinted to him she "may" be up for a 3 but no promises. He said he would love but wasn't sure what he could do since he was in a serious relationship.
A few months later there is an opportunity for her to visit me in my town and we agree to message my roommate to see if he would be there. He responds he wont but maybe a week later. She wants to meet him so she adjusts her schedule a week and I let him know. A few days before she will be here I ask him if he wants to meet her and I for drinks which he says YES. At this point nothing promised but we all assumed that it could and may likely happen.
The day arrives and I pick her up at the airport. We were both excited to see each other but try to save ourselves (or at least me) in case things happen later. I took her to her hotel (she always got a hotel even though I had a place) and once in room I couldn't control myself as I wanted her.
We kissed and I started touching her as I removed her clothes. As I said, she is blonde, blue eyes, 5'10" with a perfectly toned body. I kissed her from the lips to the neck and down her body until I tasted her shaved pussy.
I stayed there using my mouth and fingers as she was on her back enjoying. She started to react more strongly until she exploded against me and came hard. She loves to suck so she put me in her mouth and fluffed me but knew I didn't want to cum yet. I got on top of her and slid inside and enjoyed how tight she is and I had to feel it a little now assuming I will later. I have a 7"+ cock that is very thick.
Before I could finish I pulled out, we kissed and agreed to get dressed. She handled some home and work issues before we headed out. We both asked each other if we were sure we wanted to do this. We agreed YES for now, but lets see how drinks/dinner goes. We agreed on a code word if either was uncomfortable and wanted to stop things.
My roommate had suggested a bar/restaurant to meet and it worked out as we sat at the bar on the end corner with her in the middle so was easy for them to chat and get to know each other and all of us to chat without looking around each other. We enjoyed a few drinks, had a light dinner and decided to go to the apartment for a drink. Nothing was agreed to at this point but I think everyone was thinking something will happen as we all hit it off so well.
She and I discussed on the drive home if we still wanted, she said yes she wanted if I thought he did. We got to the apartment well before him so she said when he comes in she will be in our room and asked me to ask him if he was interested in more happening or specifically a blowjob as she didn't want to be embarrassed by offering and he rejected, not because he didn't think she was hot but because of his relationship.
She went to freshen up and was in my room when he arrived so I asked him his thoughts and if he was interested, he immediately said yes would love, but wanted to go shower first. He left to shower as I went in my room to tell her he wanted. She smiled and we kissed as she pulled out some lingerie and a sexy blouse.
She joined me in the living room and we chatted on the couch. While nervous she told me she wanted this very much. We kissed and touched as we waited for him to come out.
A few minutes later he joined us and once he saw her he was blown away. We were standing near the bar as I had poured some shots and he commented to her that he may have seen these before as he touched her emerald panties and blouse. I am not sure if he meant her lingerie as he had seen pictures of her wearing or her body as he had seen as well. He hugged her and commented how hot she looked. This excited her as she loves being complimented.
We did the shots and toasted each other and went to the couch. She sat between us. I kissed her and looked her in the eyes and asked if she was ok. She said yes, I really want. I unbuttoned the one button on her blouse and exposed her as she turned toward him and started kissing him.
They kissed for a long time as she reached back and touched me from outside my shorts. She was touching him with her other hand through the bottom of his shorts. She continued kissing him as they both started touching. I stood up and pulled my shorts down as my shirt was already off and sat back down to give her easier access.
I kissed her neck and started touching her breast while they kissed, she had pulled his cock out and I could see her stroking him. They kissed for a minute or so more as he touched her breasts and moved his hand lower. She tugged at his shorts so he paused and stood up and removed them and he and I were both naked.
She dropped to her knees in front of us and started sucking him as she stroked me. His cock was about 6" and she immediately took him all the way in her mouth. He was loving and watched her closely as he made sure her hair was always behind her and out of the way.
We were both touching her breasts while she sucked him and I removed her blouse as she continued. She sucked him for what seemed like 10 minutes as she stroked me most of the time to keep me puffy. He had not finished yet but she moved over to suck me and stroke him.
As she took me in her mouth and I hardened, he got off the couch and went behind her. He touched her and told her how much he loved her ass and how she felt, he put some coconut oil on his fingers as he started touching her. He was slapping her pussy and asked her if she liked, which she said "yes". She looked me in the eyes while he used his fingers. He removed her panties as she lifted her legs to help him.
