Ask A Very Smart Brotha: He Held On To The Condom The Whole Time During Sex

September 11, 2013  |  
Dear Very Smart Brotha,

A guy approached me and asked me for my number a couple of weeks ago while I was pumping gas.  The attraction was immediate on my part and after a little chit chat we did exchange numbers.  Fast forward 2 weeks, we’ve had very exciting phone conversation every night and I know a little about his life- he is 48, lives alone, has 3 children, (all by different ladies), 2 grown and a 4 year old that he has every weekend he’s off and he’s been married once and divorced. Also he had not been in a relationship he said in over a year. I’m 51, divorced for years, with 4 grown kids.  A week after meeting him, he asked me to come to his house, which I did even though I kind of had a few misgivings about it, but I only ended up staying about 20 minutes talking in his driveway and he seemed pretty taken with me.  He almost could not keep up conversation from smiling so much. It was nice.

Second week and  second “date” he asked  me to come by on a Friday night to watch movies, order take out and chill with him and his son. Well, It ended up his son was not there(grandmother came and got him because he, the guy had to work the next morning) so we ended up spending time alone. Well, we ended up kissing and cuddling and things got a little hot and bothered.  We had had the ‘getting tested’ talk before but I didn’t push it because I did not expect to have sex anytime soon with him.  So when it looked like he was trying to initiate more than heavy petting, I brought the subject up again, explaining to him that I did not feel comfortable going any further. Even though our chemistry was amazing, I just did not know him well enough to share my girly parts yet. He kept insisting he was good, that he had a test about a year ago, and he had not been with anyone since and not to worry, and that he knew from our conversations that he wanted me to be his lady so it was all good.  I kept insisting I was not going any further without one, that he could show me a copy of those or he could go to any community center and get one done for free. Well he ended up  initiating oral sex and since it’s been a while for me also, it was really hard to resist, but I ended up  literally pushing him off of me. He apologized and said it was because it had been so long and it wouldn’t happen again.  Okay, Sunday night, he has to go to work and asked me to come see him before he goes to work.  His son is there and we are sitting watching the game as I’m getting to talk to son a little bit.  He goes to meet the mother to drop the son off , leaves me there, comes back and proceeds to initiate the kissing game again. Once again he tries to do the oral and I again bring up ‘getting his freedom papers’. (btw, mine were done in April, all good). After some discussion with him being a little upset that I did not trust him and like him as much as he did me,  I reluctantly agreed to continue, using a condom.

When he got the condom out, he admitted that condoms turn him off and once he put it on his erection was not so erected.  I told him if he did not use it , we could not continue. He did, holding it on the whole time and he managed to relieve himself in 2.8 seconds. But the condom came off and I ended up having to dig it up out of myself.  I then got really upset with not only him, but myself.   I  told him I was not coming back to his house until he could respect me and my wishes and get tested.  He kept saying  that he was good and please come back, he liked me a lot and we would talk about it the next time. Before leaving I told him I was not happy, at all with the course of events. We ended up talking the next morning and we did not discuss the night before. Neither one of us brought it up and it was almost like it never happened. Before  hanging up, he asked me to call him on my break or when I got off work. We hung up and have not talked since.  I did not call him and he has not called me. He knew I was upset and to express this, I did not call him. I thought he would at least call me if he was at all interested in keeping things going. He seemed to really like me and I really liked him.  All I wanted was his ‘freedom papers’!! My question? What went wrong or better yet, did I do something wrong? Please let me know if I was too hard on him. Thanks! (P.S. I call them freedom papers because after I see that you are clean, then you are free to do almost whatever you want with me! LOL)

Troubled by the Tip

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