Straight Male / 42
Doing An Unexpected Favor For My Wife's Colleague
This happened last week, and incredibly, things seems to be just starting. It's a bit long, but needs to get off my chest.
My wife and I moved for her job. Her colleagues have been really friendly and we have established some deeper ties with one of her female colleagues, whom I will call H (single mom). She has a 20-yo daughter (R), quite attractive and petite. R is shy, a bit lonely, but very smart and kind. I've interacted with H and R separately and together.
Last Saturday, after a gathering with friends, H grabbed me to have a talk. My wife was not around due to a trip, which H knew. Usually it's been chitchat and family stories, but not this time.
Long story short, H has been concerned for how lonely her daughter is, including zero experience in the sex department. That led her to worry about how her first sex experience would lead to someone either hurting her or manipulating her, and how she wanted someone she can trust for R's first time in bed. It was a surprise, and I was very hesitant at first given how unusual the request was.
We discussed at length implications, avoiding an unwanted pregnancy, how R would feel (apparently, she fancies me), and H told me all would be discreet to make sure all is good. Were I to proceed, it would be at her house to make sure R safe. I ended up saying yes very nervously, and the plan was set in motion for the next day.
H told my wife I would help R with college stuff during Sunday afternoon (I've done that every once and then, not suspicious). I arrived well groomed and dressed, with a box of chocolate. H wore a short summerly dress, and R had a sexy tank top with a miniskirt (visibly no underwear), quite anxious.
We all sat in the living room sofa first (H, me , R). H went through the rules we had discussed, and I asked R in no vague terms that she could back off at any moment. I could tell H was aroused and wearing no underwear either. Originally, I was to take R to her room, close the door, and do the deed, but H said she wanted to observe there too to make sure all was good.
R took my hand very shakily and we all went to her room. I started by hugging and holding her in my arms, telling R to breath deeply and relax. I felt her less agitated, and went in for a kiss; I expected to go slow, but R french kissed me from the start and took me to her bed. H was watching from a recliner in the room, which made be a bit self conscious; I got permission with a glance to go ahead.
R laid on her back, me on top, I slightly pressed my body against her to grind my erection on her pussy. What a moan she gave!!! I took her large tits out of the tank top and started licking them and plating with her nipples. Then, I went down and gave her a proper oral sex session that left her gasping a couple times. R pulled me up, we kissed again, and she started undressing me. I could her H's hand rubbing against the fabric of her dress.
I showed R how to give head, and H gave her a few tips from the sofa. It took all my will not to cum on her mouth like a hose. At this point we were both completely naked, and I had bought lube for the cherry popping moment. We went slow, I eased her nerves and after a few minutes of pain, I could sense R's pussy lubricating; she said she wanted to go on top and we fucked for about 10 minutes before I filled up the first condom. She was sweating over me, hardest nipples ever on my chest. I asked her to lay down, she still shaking from her orgasm, and I ate her ass hard and spanked her a bit. H was so horny, I could tell.
I started putting a finger in her ass, but R told me she was scared and wanted only regular sex for now. We did it a couple more times (she moans very loudly), and she ended up tired and curled up in my chest. After sensing she was satisfied, I said it was time.
As I picked up my stuff, H told me to follow her to for me to take a shower. I enter and she did too, closing the door. She kissed me, took the remaining condom off and gave me a savage blowjob. H said that I had earned fucking her ass, and called R to watch. I sure gave the daughter a show, R's eyes were wide open as my dick pounded her mom's anus. She was dripping wet and told me that she wanted to learn more.
Finally, I got a french kiss from R and a slap in the butt by H and parted, and was told I can visit R whenever I want. As agreed no communication on this. All this took about three hours.
It seems this summer I'll be doing a bit of unexpected tutoring.
My wife and I moved for her job. Her colleagues have been really friendly and we have established some deeper ties with one of her female colleagues, whom I will call H (single mom). She has a 20-yo daughter (R), quite attractive and petite. R is shy, a bit lonely, but very smart and kind. I've interacted with H and R separately and together.
Last Saturday, after a gathering with friends, H grabbed me to have a talk. My wife was not around due to a trip, which H knew. Usually it's been chitchat and family stories, but not this time.
Long story short, H has been concerned for how lonely her daughter is, including zero experience in the sex department. That led her to worry about how her first sex experience would lead to someone either hurting her or manipulating her, and how she wanted someone she can trust for R's first time in bed. It was a surprise, and I was very hesitant at first given how unusual the request was.
We discussed at length implications, avoiding an unwanted pregnancy, how R would feel (apparently, she fancies me), and H told me all would be discreet to make sure all is good. Were I to proceed, it would be at her house to make sure R safe. I ended up saying yes very nervously, and the plan was set in motion for the next day.
H told my wife I would help R with college stuff during Sunday afternoon (I've done that every once and then, not suspicious). I arrived well groomed and dressed, with a box of chocolate. H wore a short summerly dress, and R had a sexy tank top with a miniskirt (visibly no underwear), quite anxious.
We all sat in the living room sofa first (H, me , R). H went through the rules we had discussed, and I asked R in no vague terms that she could back off at any moment. I could tell H was aroused and wearing no underwear either. Originally, I was to take R to her room, close the door, and do the deed, but H said she wanted to observe there too to make sure all was good.
R took my hand very shakily and we all went to her room. I started by hugging and holding her in my arms, telling R to breath deeply and relax. I felt her less agitated, and went in for a kiss; I expected to go slow, but R french kissed me from the start and took me to her bed. H was watching from a recliner in the room, which made be a bit self conscious; I got permission with a glance to go ahead.
R laid on her back, me on top, I slightly pressed my body against her to grind my erection on her pussy. What a moan she gave!!! I took her large tits out of the tank top and started licking them and plating with her nipples. Then, I went down and gave her a proper oral sex session that left her gasping a couple times. R pulled me up, we kissed again, and she started undressing me. I could her H's hand rubbing against the fabric of her dress.
I showed R how to give head, and H gave her a few tips from the sofa. It took all my will not to cum on her mouth like a hose. At this point we were both completely naked, and I had bought lube for the cherry popping moment. We went slow, I eased her nerves and after a few minutes of pain, I could sense R's pussy lubricating; she said she wanted to go on top and we fucked for about 10 minutes before I filled up the first condom. She was sweating over me, hardest nipples ever on my chest. I asked her to lay down, she still shaking from her orgasm, and I ate her ass hard and spanked her a bit. H was so horny, I could tell.
I started putting a finger in her ass, but R told me she was scared and wanted only regular sex for now. We did it a couple more times (she moans very loudly), and she ended up tired and curled up in my chest. After sensing she was satisfied, I said it was time.
As I picked up my stuff, H told me to follow her to for me to take a shower. I enter and she did too, closing the door. She kissed me, took the remaining condom off and gave me a savage blowjob. H said that I had earned fucking her ass, and called R to watch. I sure gave the daughter a show, R's eyes were wide open as my dick pounded her mom's anus. She was dripping wet and told me that she wanted to learn more.
Finally, I got a french kiss from R and a slap in the butt by H and parted, and was told I can visit R whenever I want. As agreed no communication on this. All this took about three hours.
It seems this summer I'll be doing a bit of unexpected tutoring.
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