I lost my virginity at 21 in the weirdest way. On my birthday, my sister who was 18, asked if I had any goals – if I had gotten laid yet and I said no.
She was laughing and asked how I still haven’t lost it to a girl and I said I never had the chance. She then said she can turn me into a man since I turned 21, and I asked for clarification.
My sister said she could help me do something I want – but with a catch. I would be able to try sex with her using a condom (no kissing, touching, or seeing her visually) with the catch that I swallow the sperm in the condom afterwards.
I asked why she wanted me to do that and she said if she is sacrificing some of her dignity to do a favor, I need to do something in return that is humiliating.
I was up for it and asked her how it would go down, she said to go to her bedroom at 1 AM when everyone was asleep – and to bring light pants, a few condoms, and a plastic cup.
I took her awkward request and anxiously waited for the hour, watching porn in the mean time and feeling excited to finally gain my manhood. My sister texted me at 12:30 AM, saying she would be fully clothed except no pants or underwear on. However she’d be covered by the blankets and her ground rules were, no kissing, physical touch, and I could not see her body, but I would have to let her see me naked. I did not mind the double standards as I was grateful enough she would sacrifice some of her dignity to let me have a favor.
Before I went to her room, I wore very light pants with no underwear on for ease of taking it off, then I took the pack of condoms and cup as I crept into her room. I saw her waiting under the blankets and she set the rules that I could not lift the blankets, kiss her ANYWHERE, or touch any part of her body.
She made me undress in front of her by lowering my pants as she smiled, then I took one of the condoms I brought to open it and roll it down my penis. I was not ready yet as the nervousness made it difficult to get hard, but I had to stimulate my penis as she watched it finally get hard. Afterwards she told me to get in the blanket without looking underneath, then she faced the pillow to have her rear side on top.
I felt her legs as I got on top and had trouble guiding my penis to the right hole. I asked her for help so she spread her legs, took her hand to grab my penis and guide it into the right place and told me to push. As I did that, I felt the warmth, and her vagina muscles gripping as I put it in. I asked why her body was so warm and said it feels wet and nice.
Afterwards, she set a timer for 6 minutes and said I am free to try as much as I want but whatever I release, I would have to eat later. I was excited and started my action, it was wet, warm, and kept gripping my penis with her muscles as I took full advantage of the 6 minutes and released a few times – knowing the fate of what would have to happen later.
When the 6 minutes were over, she pulled it out and told me to stop, then I got out of her bed and had an erect penis full of cum. As she saw it, she said ‘gross’ and I jokingly said this was all meant for you. She said ‘eww you’re my brother’ and I said ‘and I just got laid.’
After I awkwardly opened up the condom and she told me to pour it into the cup. Afterwards I felt disgust but knew this was the price I had to pay for getting some action, I quickly took it down without tasting it, feeling disgusted.
I left the room to dispose the cup, wash my penis, and brush my teeth and rinse my mouth. Afterwards I texted her to tell me when she was done dressing, and I went back to her room to ask how she felt. She said she was grossed out but was glad I am finally a man. Afterwards as a goodbye I asked if I could just kiss her vagina from the outside without seeing it, which she could not understand but she said fine.
She sat down and I kissed it, saying ‘thank you for finally turning me into a man after 21 years of living’ and she cringed, saying it wasn’t even that big of a deal. I left afterwards and felt great.
